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dipyrone

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Description

Dipyrone, also known as meтамизол, is a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. It is a pyrazolone derivative that was first synthesized in 1920. Dipyrone is a potent inhibitor of cyclooxygenase (COX), an enzyme involved in the production of prostaglandins, which are mediators of pain and inflammation. It is also thought to have central nervous system effects, contributing to its analgesic properties. Dipyrone is widely used worldwide for the treatment of mild to moderate pain, fever, and inflammation. However, it has been associated with serious adverse effects, including agranulocytosis (a potentially fatal condition characterized by a severe decrease in white blood cells) and hypersensitivity reactions. Due to these risks, dipyrone has been withdrawn from the market in many countries, including the United States. However, it remains widely available in other parts of the world. Research on dipyrone continues, focusing on its mechanism of action, its potential benefits and risks, and its use in specific populations, such as children and pregnant women. Studies are also exploring the development of safer and more effective alternatives to dipyrone.'

metamizole : A pyrazole that is antiipyrine substituted at C-4 by a methyl(sulfomethyl)amino group, the sodium salt of which, metamizole sodium, was widely used as a powerful analgesic and antipyretic, but withdrawn from many markets from the 1970s due to a risk of causing risk of causing agranulocytosis. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Dipyrone: A drug that has analgesic, anti-inflammatory, and antipyretic properties. It is the sodium sulfonate of AMINOPYRINE. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

metamizole sodium : An organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3111
CHEMBL ID461522
CHEBI ID62088
SCHEMBL ID24997
MeSH IDM0006535
PubMed CID522325
CHEMBL ID487894
CHEBI ID59033
SCHEMBL ID24996
MeSH IDM0006535

Synonyms (258)

Synonym
BRD-K76812510-236-05-6
DIVK1C_000634
KBIO1_000634
metamizolum
methamizole
metamizol
SPECTRUM_001681
BPBIO1_001019
PRESTWICK2_000713
BSPBIO_003182
PRESTWICK3_000713
IDI1_000634
SPECTRUM5_001215
methanesulfonic acid, 1-((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino)-
BSPBIO_000925
metamizole
DB04817
KBIO3_002682
KBIOSS_002161
KBIO2_007297
KBIO2_002161
KBIOGR_000805
KBIO2_004729 ,
SPECTRUM4_000203
SPBIO_001426
PRESTWICK0_000713
SPECTRUM3_001591
PRESTWICK1_000713
SPBIO_002846
NINDS_000634
SPECTRUM2_001553
D08188
50567-35-6
dolemicin (tn)
((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino)methanesulphonic acid
chebi:62088 ,
CHEMBL461522
[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonic acid
n-(2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-n-methylaminomethanesulfonic acid
(antipyrinylmethylamino)methanesulfonic acid
[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino]methanesulfonic acid
[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)(methyl)amino]methanesulfonic acid
n-methyl-n-(2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)aminomethanesulfosaeure
einecs 256-627-7
novamine sulfone
934t64rmnj ,
unii-934t64rmnj
pyridone
methanesulfonic acid, ((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino)-
methanesulfonic acid, (antipyrinylmethylamino)-
methamizole-
metamizole [who-dd]
SCHEMBL24997
sulpyrine (salt/mix)
methanesulfonic acid, 1-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino]-
analgin (salt/mix)
metamizole sodium salt (salt/mix)
melubrin, methyl-
metapyrin (salt/mix)
analgine (salt/mix)
methanesulfonic acid, [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino]-
LVWZTYCIRDMTEY-UHFFFAOYSA-N
noramidopyrine methanesulfonic acid
novalgin (salt/mix)
dipyrone (salt/mix)
optalgin (salt/mix)
DTXSID6044143 ,
metamizole sodium ;analgin
[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino]methanesulphonic acid
bdbm235671
Q56719288
gtpl10608
EN300-18537230
CS-0613716
HY-148147
dolemicin
dtxcid4024143
((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino)methanesulfonic acid
((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)(methyl)amino)methanesulfonic acid
chebi:59033 ,
mexican aspirin
metamizole sodique
vetalgin
analgin (sodium salt)
meamizol sodico
dipyrone [anhydrous]
methampyrone
sodium [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)(methyl)amino]methanesulfonate
ccris 4443
sulpyrinum
noramidopyrine methanesulfonate sodium
methanesulfonic acid, (antipyrinylmethylamino)-, monosodium salt
sodium noramidopyrine methanesulfonate
methylaminophenyldimethylpyrazolone methanesulfonate sodium
dipyrone (anhydrous)
phenyl dimethyl pyrazolon methyl aminomethane sodium sulfonate
4-sodium methanesulfonate methylamine-antipyrine
4-methylamino-1,5-dimethyl-2-phenyl-3-pyrazolone sodium methanesulfonate
keypyrone
natrium novaminsulfonicum
sodium ((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino)methanesulphonate
metamizole sodium
novaminsulfone sodium
metamizolum natricum [inn-latin]
pharmalgine
novaminophenazone
algocalmin
di-podil
novaminsulfone
diprofarn
metamizole sodique [french]
methanesulfonic acid, ((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino)-, sodium salt
metamizolnatrium
noraminophenazone sodium mesylate
algopyrine
sodium 1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylamino methanesulfonate
metapyrin
farmolisina
novamidazophen
novaminsulfonum
(antipyrinylmethylamino)methanesulfonic acid sodium salt
antipyrine, 4-(methylamino)-, monomethosulfate, sodium salt
1-phenyl-2,3-dimethyl-4-methylamino-5-pyrazolon-n-methanesulfonsaeuren natrium [german]
methanesulfonic acid, (antipyrinylmethylamino)-, sodium salt
nevralgina
novalgin
neo-melubrine
metilon
narone
novamidazophenum
dipyrone anhydrous
alginodia
barone
pyretin
neomelurbrin
bonpyrin
arpf
paralgin
1-phenyl-2,3-dimethylpyrazolone-(5)-4-methylaminomethanesulfonic acid sodium
pyrojec
optalgin
novaminsulfonium
1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethanesulfonate sodium
noveltex
methylmelubrin
analginum
sulpin
methylaminoantipyrine sodium methanesulfonate
metamizolo [italian]
novalgetol
sodium phenyldimethylpyrazolon-methylamino-methane sulfonate
novaminsulfon
noraminophenazone
noramidopyrine methanesulfonate sodium salt
sulpyrin
fenildimetil-pirazolon-metilaminometansolfonato sodico [italian]
conmel
analgin
noraminophenazone methanesulfonate sodium salt
dimethone
dipyrone [ban]
aminopyrine sodium sulfonate
metamizolum natricum [latin]
metamizole sodique [inn-french]
metamizolum natricum
noraminopyrine methanesulfonate sodium
sodium (antipyrinylmethylamino)methanesulfonate
pyralgin
metamizolo sodico [dcit]
sodium 4-methylamino-1,5-dimethyl-2-phenyl-3-pyrazolone 4-methanesulfonate
noramidopyrinium-methanesulphate natrium [german]
sodium methylaminoantipyrine methanesulfonate
einecs 200-694-7
pyretin (pharmaceutical)
fevonil
sodium novaminsulfonate
metamizol sodico [spanish]
gifaril
sodium 1-phenyl-2,3-dimethyl-4-methylaminopyrazolon-n-methanesulfonate
feverall
analgine
68-89-3
PRESTWICK_987
NCGC00017049-01
cas-5907-38-0
dipyrone
NCGC00095040-02
NCGC00095040-01
SPECTRUM1503298
HMS2093C17
D08190
dipyrone (ban)
vetalgin (tn)
HMS501P16
CHEMBL487894
dipyrone sodium
HMS1922A06
HMS1570O07
HMS2097O07
tox21_200497
NCGC00258051-01
dtxcid20543
cas-68-89-3
dtxsid8020543 ,
tox21_110759
CCG-39331
NCGC00017049-02
NCGC00017049-03
methamizole sodium
fenildimetil-pirazolon-metilaminometansolfonato sodico
metamizol sodico
prodolina
metamizolo
vsu62z74on ,
metamizolo sodico
dipyrone [usan:ban:jan]
dipyrone [usan:jan]
noramidopyrinium-methanesulphate natrium
metamizole sodium [inn]
metamizol sodico [inn-spanish]
1-phenyl-2,3-dimethyl-4-methylamino-5-pyrazolon-n-methanesulfonsaeuren natrium
unii-vsu62z74on
FT-0602853
metamizole sodium (anhydrous)
sodium 1-phenyl-2,3-dimethyl-4-methylaminopyrazolon-n-methanesulphonate
metamizole sodium [who-dd]
metamizolum natricum anhydricum
metamizole sodium [ep impurity]
noramidopyrine methanesulphonate sodium
EPITOPE ID:124939
AKOS015904648
SCHEMBL24996
NCGC00178220-05
tox21_110759_1
DJGAAPFSPWAYTJ-UHFFFAOYSA-M
methylmelubrine
methanesulfonic acid, [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino]-, sodium salt
sodium ((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)(methyl)amino)methanesulfonate
sodium;[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonate
metamizol sodium
HMS3714O07
M3060
F20711
dipyrone,(s)
mfcd00020783
metamizole sodium salt
Q422761
68-89-3 (sodium)
AS-81983
CS-0013577
HY-B1279A
metamizole (sodium)
methanesulfonic acid, 1-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)methylamino]-, sodium salt (1:1)
metamizolum natricum (latin)
metamizole sodium monohydrate (ep monograph)
nsc73205
metamizole sodique (inn-french)
metamizole sodium (ep impurity)

Research Excerpts

Toxicity

We identified epidemiologic studies, published from January 1970 to December 1995. Dipyrone was associated with significantly less self-reported adverse effects and these were not significantly different from those under placebo. In conclusion, the dipyrone formulation is effective and safe for clinical medication.

ExcerptReferenceRelevance
" We identified epidemiologic studies, published from January 1970 to December 1995, that investigated the association of serious adverse effects with aspirin, diclofenac, acetaminophen, and dipyrone to determine and compare the excess mortality associated with short-term drug use."( Comparative safety evaluation of non-narcotic analgesics.
Andrade, SE; Martinez, C; Walker, AM, 1998
)
0.3
" A significantly higher percentage of adverse gastrointestinal effects was found in patients given tramadol (42."( Efficacy and safety of dipyrone versus tramadol in the management of pain after hysterectomy: a randomized, double-blind, multicenter study.
Cabrera, J; Calderón, E; Cámara, J; de la Torre, MR; García-Magaz, I; Gómez, JL; Herrera, J; Martínez, T; Montero, A; Ortiz, P; Porres, R; Rodríguez, MJ; Ruiz, J; Torres, LM,
)
0.13
" All medications including placebo were almost equally safe and well tolerated."( Efficacy and safety of metamizol vs. acetylsalicylic acid in patients with moderate episodic tension-type headache: a randomized, double-blind, placebo- and active-controlled, multicentre study.
Cámara, J; Cornet, ME; Despuig, J; Díez-Tejedor, E; Fragoso, YD; Leira, R; Liaño, H; Martínez-Martín, P; Ortiz, P; Peil, H; Raffaelli, E; Titus, F; van Toor, BS; Vix, JM, 2001
)
0.31
"6 x 10(3) mg l(-1)) that was non-toxic for bioassays based on fish (Carassius auratus gibelio) and hydra (Hydra attenuata) and acutely toxic for bioassays with ceriodaphnia (Ceriodaphnia affinis) and onion (Allium cepa)."( Use of a complex approach for assessment of metamizole sodium and acetylsalicylic acid toxicity, genotoxicity and cytotoxicity.
Arkhipchuk, VV; Chernykh, VP; Goncharuk, VV; Gritsenko, IS; Maloshtan, LN,
)
0.13
"Controlled oral challenge with nonsteroidal anti-inflammatory drugs (NSAIDs) is the only definite way to detect safe NSAIDs in patients with NSAID-induced anaphylactoid reactions."( Safety of the new selective cyclooxygenase type 2 inhibitors rofecoxib and celecoxib in patients with anaphylactoid reactions to nonsteroidal anti-inflammatory drugs.
Conde, J; Delgado, J; Florido, JF; López-Pascual, E; Nieto, MA; Ortega, N; Quiralte, J; Sáenz de San Pedro, B, 2004
)
0.32
"The SBPCOCs with highly selective COX-2 inhibitors were safe in patients with single-reactive, NSAID-induced anaphylactoid reactions, even in cases that involved pyrazole derivatives."( Safety of the new selective cyclooxygenase type 2 inhibitors rofecoxib and celecoxib in patients with anaphylactoid reactions to nonsteroidal anti-inflammatory drugs.
Conde, J; Delgado, J; Florido, JF; López-Pascual, E; Nieto, MA; Ortega, N; Quiralte, J; Sáenz de San Pedro, B, 2004
)
0.32
" We conclude that dipyrone is an effective, safe and cost-effective option in acute migraine management."( The efficacy and safety of dipyrone (Novalgin) tablets in the treatment of acute migraine attacks: a double-blind, cross-over, randomized, placebo-controlled, multi-center study.
Boz, C; Erdemoglu, AK; Ergün, H; Göksan, B; Gülmez, SE; Inan, L; Ozbenli, T; Ozmenoğlu, M; Tulunay, FC; Varlikbas, A,
)
0.13
" In conclusion, the dipyrone formulation is effective and safe for clinical medication."( Pharmacodynamics and potential toxicity of intranasally administered dipyrone.
Bi, D; Mao, S; Yang, S, 2006
)
0.33
" Finally, the application of an acute toxicity test (Daphnia magna) showed an increase in toxicity during the photolytic process, a consequence of the formation of toxic photoproducts."( Photodegradation study of three dipyrone metabolites in various water systems: identification and toxicity of their photodegradation products.
Agüera, A; Fernández-Alba, AR; Gómez, MJ; Mezcua, M; Sirtori, C, 2008
)
0.35
" According to the Uppsala Monitoring Centre, WHO Collaborating Centre for International Drug Monitoring, the number of adverse effects registered in the years 1978-2009 (March) was 14441 for metamizol and 67581 for paracetamol."( [Safety of metamizole and paracetamol for acute pain treatment].
Kotfis, K; Zukowski, M,
)
0.13
"The frequency of adverse effects (including therapeutic failure) with the medications tramadol and dipirona were described and estimated."( [Adverse events associated with tramadol and dipirona administration in a level III hospital].
Montoya, GA; Parra, MF; Vaca, C, 2009
)
0.35
", Colombia, adverse events associated with dipirone and tramadol were rigorously tracked in patients hospitalized in the internal medicine, as well as the orthopedics and surgery departments."( [Adverse events associated with tramadol and dipirona administration in a level III hospital].
Montoya, GA; Parra, MF; Vaca, C, 2009
)
0.35
"6% (16 cases) were classes as serious adverse events."( [Adverse events associated with tramadol and dipirona administration in a level III hospital].
Montoya, GA; Parra, MF; Vaca, C, 2009
)
0.35
"An unacceptable level of preventable adverse events was described that impacted the well-being of patients, as well as the costs associated with remedial treatment."( [Adverse events associated with tramadol and dipirona administration in a level III hospital].
Montoya, GA; Parra, MF; Vaca, C, 2009
)
0.35
"To evaluate the ability of atropine sulfate, butylscopolammonium bromide combined with metamizole sodium, and flunixin meglumine to ameliorate the clinical adverse effects of imidocarb dipropionate in horses."( Evaluation of the use of atropine sulfate, a combination of butylscopolammonium bromide and metamizole sodium, and flunixin meglumine to ameliorate clinical adverse effects of imidocarb dipropionate in horses.
Abutarbush, SM; Al-Majali, AM; Alfaqeeh, SM; Mustafa, G; Qura'n, L, 2013
)
0.39
"Imidocarb dipropionate use in the control group was associated with serious adverse effects including signs of abdominal pain (4/7 horses) and diarrhea (2/7)."( Evaluation of the use of atropine sulfate, a combination of butylscopolammonium bromide and metamizole sodium, and flunixin meglumine to ameliorate clinical adverse effects of imidocarb dipropionate in horses.
Abutarbush, SM; Al-Majali, AM; Alfaqeeh, SM; Mustafa, G; Qura'n, L, 2013
)
0.39
"A combination of butylscopolammonium bromide and metamizole sodium may be useful to ameliorate the adverse effects of imidocarb dipropionate in horses, although group size was small and significant differences from the control group were not found."( Evaluation of the use of atropine sulfate, a combination of butylscopolammonium bromide and metamizole sodium, and flunixin meglumine to ameliorate clinical adverse effects of imidocarb dipropionate in horses.
Abutarbush, SM; Al-Majali, AM; Alfaqeeh, SM; Mustafa, G; Qura'n, L, 2013
)
0.39
" The aim of this study was to analyze individual case safety reports (ICSRs) of metamizole-associated hematological adverse drug reactions (ADRs)."( Hematological safety of metamizole: retrospective analysis of WHO and Swiss spontaneous safety reports.
Blaser, LS; Egger, P; Haschke, M; Krähenbühl, S; Rätz Bravo, AE; Tramonti, A, 2015
)
0.42
"To determine whether metamizole is clinically safe compared to placebo and other analgesics."( Metamizole-associated adverse events: a systematic review and meta-analysis.
Blozik, E; da Costa, BR; Fässler, M; Jüni, P; Kötter, T; Linde, K; Reichenbach, S; Scherer, M, 2015
)
0.42
" Adverse events (AEs), serious adverse events (SAEs), and dropouts were assessed."( Metamizole-associated adverse events: a systematic review and meta-analysis.
Blozik, E; da Costa, BR; Fässler, M; Jüni, P; Kötter, T; Linde, K; Reichenbach, S; Scherer, M, 2015
)
0.42
"For short-term use in the hospital setting, metamizole seems to be a safe choice when compared to other widely used analgesics."( Metamizole-associated adverse events: a systematic review and meta-analysis.
Blozik, E; da Costa, BR; Fässler, M; Jüni, P; Kötter, T; Linde, K; Reichenbach, S; Scherer, M, 2015
)
0.42
"Due to possible serious adverse drug reactions (ADRs), the use of metamizole for postoperative pain therapy in children is a subject of debate."( Metamizole for postoperative pain therapy in 1177 children: A prospective, multicentre, observational, postauthorisation safety study.
Badelt, G; Becke, K; Boethig, D; Eich, C; Fieler, M; Leimkühler, K; Messroghli, L; Sümpelmann, R, 2015
)
0.42
" No respiratory adverse events directly related to the metamizole administration and no clinical signs of agranulocytosis were reported."( Metamizole for postoperative pain therapy in 1177 children: A prospective, multicentre, observational, postauthorisation safety study.
Badelt, G; Becke, K; Boethig, D; Eich, C; Fieler, M; Leimkühler, K; Messroghli, L; Sümpelmann, R, 2015
)
0.42
" Over the past several decades, a number of epidemiologic studies have been conducted to quantify the risk of agranulocytosis and other adverse effects associated with metamizole and other non-narcotic analgesics."( Safety of metamizole: a systematic review of the literature.
Andrade, S; Bartels, DB; Gurwitz, J; Lange, R; Sandford, L, 2016
)
0.43
"Published studies reported differences in the magnitude of risk of adverse outcomes associated with metamizole use and often had small sample sizes and a number of other limitations that may have biased the results."( Safety of metamizole: a systematic review of the literature.
Andrade, S; Bartels, DB; Gurwitz, J; Lange, R; Sandford, L, 2016
)
0.43
" Metamizole is also infamous because of its potential fatal adverse drug reaction, agranulocytosis."( Chronic use of metamizole: not so safe after all?
Herbers, AH; Koehestanie, P; Terhaar Sive Droste, JS; Vuik, FE, 2017
)
0.46
" In a previous study, we have shown that N-methyl-4-aminoantipyrine (MAA), the active metamizole metabolite, reacts with hemin and forms an electrophilic metabolite that is toxic for HL60 cells, but not for mature neutrophil granulocytes."( Toxicity of metamizole on differentiating HL60 cells and human neutrophil granulocytes.
Duthaler, U; Krähenbühl, S; Roos, NJ; Rudin, D, 2019
)
0.51
" The anti-tumor effect is often accompanied by immune-related adverse events (irAE)."( Challenges in diagnosis and management of neutropenia upon exposure to immune-checkpoint inhibitors: meta-analysis of a rare immune-related adverse side effect.
Boegeholz, J; Brueggen, CS; Dimitriou, F; Dummer, R; Haralambieva, E; Manz, MG; Pauli, C; Widmer, CC, 2020
)
0.56
"To analyze whether the drug safety update issued by the Spanish Agency of Medicines and Healthcare Products (AEMPS), dated October 30, 2018, on agranulocytosis and metamizole contains accurate and necessary information to protect patients from the presentation of this adverse reaction (AR) and if the official documentation of medicines containing metamizole for doctors, pharmacists and the general population conforms to the guidelines of the AEMPS to reduce this risk."( [Adequacy of the safety of metamizole and agranulocytosis].
Garcia Del Campo, C; Martinez-Mir, I; Murcia Soler, M; Palop Larrea, V,
)
0.13
" However, dipyrone was associated with significantly less self-reported adverse effects and these were not significantly different from those under placebo."( Tilidine and dipyrone (metamizole) in cold pressor pain: A pooled analysis of efficacy, tolerability, and safety in healthy volunteers.
Baumann, F; Bingel, U; Kleine-Borgmann, J; Kratel, J; Schmidt, K; Wilhelmi, J; Zunhammer, M, 2021
)
0.62
" Adverse events were not observed in patients treated with ketamine."( Efficacy and safety in ketamine-guided prehospital analgesia for abdominal pain.
Dorau, W; Eppler, F; Häske, D; Heinemann, N; Schempf, B; Schopp, T, 2022
)
0.72

Pharmacokinetics

The pharmacokinetic behaviour of dipyrone metabolite 4-MAA in serum was determined in seven horses of different breeds after a single intravenous dose administration. Plasma levels of the active dipyr one metabolite-Methylaminoantipyrine (MAA) were measured and the calculated pharmacokinetics parameters were compared.

ExcerptReferenceRelevance
" Therefore, caffeine is maximally effective in potentiating the effect of analgesics at a dose of 10 mg/kg and this potentiation is not due to a pharmacokinetic interaction with the analgesic, and also not due to phosphodiesterase (PDE) inhibition."( Determination of the optimal analgesia-potentiating dose of caffeine and a study of its effect on the pharmacokinetics of aspirin in mice.
Gayawali, K; Pandhi, P; Sharma, PL, 1991
)
0.28
"The pharmacokinetic pattern of 100 mg nimesulide administered rectally at different times prior to undergoing minor surgery was studied in 45 children."( Pharmacokinetics and therapeutic study with nimesulide suppositories in children with post-operative pain and inflammation.
Brülhart, K; Monti, T; Schärli, AF,
)
0.13
" The mean Cmax of 4-MAA increased linearly with dose whereas its AUC was not proportional to dose after administration of 1500 and 3000 mg."( Pharmacokinetics of metamizol metabolites in healthy subjects after a single oral dose of metamizol sodium.
Bacracheva, N; Badian, M; Verho, M; Vlahov, V, 1990
)
0.28
" Twenty-four hours after the first period of this pharmacokinetic study, identical parameters were evaluated under dipyrone induced normothermic conditions."( Pharmacokinetics of ceftazidime and netilmicin in patients with sepsis.
Ganzinger, U; Grimm, G; Kleinberger, G; Laggner, A; Lenz, K; Schatz, F, 1987
)
0.27
" Plasma levels of the active dipyrone metabolite-Methylaminoantipyrine (MAA) were measured and the calculated pharmacokinetic parameters were compared."( Influence of food on the pharmacokinetics of dipyrone.
Flusser, D; Granit, L; Levy, M; Zylber-Katz, E, 1988
)
0.27
"0 mg/kg) and pharmacodynamic interactions of insecticide were studied with centrally acting drugs viz."( Pharmacodynamic interactions of cypermethrin and centrally acting drugs in mice.
Kanwar, RS; Varshneya, C, 1995
)
0.29
" The elimination half-life of the final metabolites FAA and AAA can be equally evaluated from plasma and saliva data."( Validity of saliva samples for the estimation of dipyrone metabolites pharmacokinetics.
Caraco, Y; Granit, L; Levy, M; Zylber-Katz, E, 1993
)
0.29
"The pharmacokinetic behaviour of dipyrone metabolite 4-MAA in serum was determined in seven horses of different breeds after a single intravenous dose administration."( Pharmacokinetic study of dipyrone metabolite 4-MAA in the horse and possible implications for doping control.
Böttcher, M; Hapke, HJ; Klaus, AM; Kleinitz, U; Schlingloff, Y, 1997
)
0.3
" The results revealed that cimetidine interacted with 4-MAA by increasing the systemic availability, prolonging the elimination half-life and decreasing the systemic clearance of 4-MAA, whereas the renal clearances of 4-MAA remained unchanged."( Effect of cimetidine on the pharmacokinetics of the metabolites of metamizol.
Bacracheva, N; Drenska, A; Gorantcheva, J; Schinzel, S; Scholl, T; Stoinov, A; Tchakarski, I; Tentcheva, J; Tyutyulkova, N; Vlahov, V, 1997
)
0.3
" Linear regression analysis and a "jack-knife" validation procedure revealed that the AUC(0-infinity) and the Cmax of MAA can be accurately predicted (R2>0."( Limited-sampling strategy models for estimating the pharmacokinetic parameters of 4-methylaminoantipyrine, an active metabolite of dipyrone.
Estrela, RC; Ribeiro, FM; Struchiner, CJ; Suarez-Kurtz, G; Vicente, FL, 2001
)
0.31
" In addition, after the simultaneous administration of the drugs in a single dose, a pharmacokinetic interaction was found, which significantly (P<0."( Effect of metamizol on morphine pharmacokinetics and pharmacodynamics after acute and subchronic administration in arthritic rats.
Cortés-Arroyo, AR; Domínguez-Ramírez, AM; López, JR; López-Muñoz, FJ; Y de la Peña, MH, 2010
)
0.36
" Pharmacokinetics and statistical analysis: Using the population approach based on a formerly developed experimental model, the relationships between pharmacokinetic parameters and demographic and physiological covariates are explored."( Population pharmacokinetic analysis of the active product of dipyrone.
Levy, M; Muszkat, M; Rich, B; Rosenkranz, B; Schlattmann, P, 2010
)
0.36
"A population pharmacokinetic analysis of MAA, the active product of dipyrone, reveals that age is a significant predictor of MAA disposition."( Population pharmacokinetic analysis of the active product of dipyrone.
Levy, M; Muszkat, M; Rich, B; Rosenkranz, B; Schlattmann, P, 2010
)
0.36
" This review sought evidence from single dose pharmacokinetic studies on the extent and timing of peak plasma concentrations of analgesic drugs in the fed and fasting states."( Effects of food on pharmacokinetics of immediate release oral formulations of aspirin, dipyrone, paracetamol and NSAIDs - a systematic review.
Derry, S; Moore, RA; Straube, S; Wiffen, PJ, 2015
)
0.42
" Food typically delayed absorption for all drugs where the fasting tmax was less than 4 h."( Effects of food on pharmacokinetics of immediate release oral formulations of aspirin, dipyrone, paracetamol and NSAIDs - a systematic review.
Derry, S; Moore, RA; Straube, S; Wiffen, PJ, 2015
)
0.42
" Other pharmacokinetic interactions along with known pharmacodynamic interactions in which metamizol active metabolites contribute, should be considered."( Pharmacokinetics and pharmacodynamics of metamizol in co-administration with morphine under acute and chronic treatments in arthritic rats.
Carrillo-Calzadilla, PE; Cortés-Arroyo, AR; Domínguez-Ramírez, AM; López-Muñoz, FJ; Medina-López, JR; Moreno-Rocha, LA, 2017
)
0.46
"This study was performed to determine pharmacokinetic profiles of the two active metabolites of the analgesic drug metamizole (dipyrone, MET), 4-methylaminoantipyrine (MAA), and 4-aminoantipyrine (AA), after intravenous (i."( Pharmacokinetic profiles of the two major active metabolites of metamizole (dipyrone) in cats following three different routes of administration.
Chea, B; Giorgi, M; Kim, TW; Lebkowska-Wieruszewska, B; Owen, H; Poapolathep, A, 2018
)
0.48
" The aim of this study was to assess the pharmacokinetic profiles of MAA and AA after dose of 25 mg/kg MT by intravenous (i."( Pharmacokinetic profiles of the active metamizole metabolites after four different routes of administration in healthy dogs.
De Vito, V; Giorgi, M; Kim, TW; Lisowski, A; Owen, H; Poapolathep, A; Łebkowska-Wieruszewska, B, 2018
)
0.48
"This preliminary clinical investigation of the pharmacokinetic behavior of the main metamizole (dipyrone) metabolites 4-methylaminoantipyrine (4-MAA) and 4-aminoantipyrine (4-AA) in calves undergoing umbilical surgery is part of an already published main study."( Pharmacokinetics of metamizole (dipyrone) as an add-on in calves undergoing umbilical surgery.
Baumgartner, C; Behrendt-Wippermann, M; Brandl, J; Feist, M; Fux, D; Metzner, M; von Thaden, A, 2022
)
0.72
"This study aimed to determine the pharmacokinetic profile of two active metabolites of metamizole (dipyrone), N-methyl-4-aminoanthypyrine (MAA) and 4-aminoanthypyrine (AA), after intravenous administration in cats."( Pharmacokinetic profiles of the two major active metabolites of metamizole, 4-methylaminoantipyrine (MAA) and 4-aminoantipyrine (AA), after intravenous injection in cats.
Araújo-Silva, G; Arcoverde, KN; de Macêdo, LB; de Paiva, ALC; de Paula, VV; Fernandes, NS; Mouta, AN; Nunes, TL; Urizar, JTP, 2023
)
0.91

Compound-Compound Interactions

Tramadol alone, or in combination with dipyrone or meloxicam, on postoperative pain and analgesia requirement after unilateral mastectomy with or without ovariohysterectomy.

ExcerptReferenceRelevance
"In the present study we investigated the antiinflammatory effect of pentosanpolysulfate (SP 54) in combination with metamizol using different forms of rat paw edema (induced by dextrane, hyaluronidase, trypsin, formaldehyde, carragenine or kaolin)."( [Pharmacological studies on the antiphlogistic effect of pentosanpolysulfate in combination with metamizol].
Kalbhen, DA; Smalla, HD, 1977
)
0.26
" We investigated the effect of this new sexual hormone alone and in combination with ethynylestradiol on the elimination of both testdrugs."( [Effect of a new gestagen--dienogest--and its combination with ethinyl estradiol on the activity of biotransformation reactions].
Balogh, A; Hoffmann, A; Klinger, G; Liewald, S; Liewald, T; Schröder, S; Splinter, FC, 1990
)
0.28
" The participants were randomized into three prophylactic treatment groups: dexamethasone (n = 43), ondansetron in combination with dexamethasone (n = 44), and placebo (n = 42)."( Dexamethasone versus ondansetron in combination with dexamethasone for the prophylaxis of postoperative vomiting in pediatric outpatients: a double-blind, randomized, placebo-controlled clinical trial.
Borges, PS; de Orange, FA; Flores, M; Marques, J, 2012
)
0.38
"8% in the group receiving ondansetron combined with dexamethasone, 14."( Dexamethasone versus ondansetron in combination with dexamethasone for the prophylaxis of postoperative vomiting in pediatric outpatients: a double-blind, randomized, placebo-controlled clinical trial.
Borges, PS; de Orange, FA; Flores, M; Marques, J, 2012
)
0.38
"To compare the effects of tramadol alone, or in combination with dipyrone or meloxicam, on postoperative pain and analgesia requirement after unilateral mastectomy with or without ovariohysterectomy in dogs."( Effects of tramadol alone, in combination with meloxicam or dipyrone, on postoperative pain and the analgesic requirement in dogs undergoing unilateral mastectomy with or without ovariohysterectomy.
Bressan, TF; Campagnol, D; Coelho, K; Monteiro, BS; Monteiro, ER; Teixeira, RC, 2013
)
0.39
" Before the end of surgery, dogs were randomly assigned to receive intravenous tramadol alone (3 mg kg(-1), group T), combined with dipyrone (30 mg kg(-1), group TD) or meloxicam (0."( Effects of tramadol alone, in combination with meloxicam or dipyrone, on postoperative pain and the analgesic requirement in dogs undergoing unilateral mastectomy with or without ovariohysterectomy.
Bressan, TF; Campagnol, D; Coelho, K; Monteiro, BS; Monteiro, ER; Teixeira, RC, 2013
)
0.39
"Under the conditions of this study, tramadol alone or in combination with dypyrone or meloxicam provided effective analgesia for 24 hours in most dogs after unilateral mastectomy with or without ovariohysterectomy."( Effects of tramadol alone, in combination with meloxicam or dipyrone, on postoperative pain and the analgesic requirement in dogs undergoing unilateral mastectomy with or without ovariohysterectomy.
Bressan, TF; Campagnol, D; Coelho, K; Monteiro, BS; Monteiro, ER; Teixeira, RC, 2013
)
0.39
" Based on these values and on the statistical model, the impact of drug combination versus single drug as well as of reversed order was small with changes in relative recovery of smaller equal 9%."( Drug combinations and impact of experimental conditions on relative recovery in in vitro microdialysis investigations.
Burau, D; Dorn, C; Ehmann, L; Kloft, C; Kratzer, A; Petroff, D; Simon, P; Weiser, C; Wrigge, H, 2019
)
0.51
" In the case of a treatment of valproate combined with dipyrone, a close monitoring of the valproate level is recommended."( [Medicinal Complex Therapy - Drug Interaction of Valproate and Dipyrone].
Green, K; Kliem, A; Mattern, M, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
" Maximal concentration, time to peak and absorption rate of MAA were similar for both groups."( Effect of age on the pharmacokinetics of dipyrone.
Granit, L; Levy, M; Stessman, J; Zylber-Katz, E, 1989
)
0.28
" Bioavailability of ASA at intramuscular administration to rabbits was close to that at intravenous injection and significantly higher as compared with intragastric administration."( [Analgesic action and pharmacokinetics of lysine acetylsalicylate administered intramuscularly].
Chaĭka, LA; Khadzhaĭ, IaI; Kosheleva, LP; Libina, VV; Pichugin, VV,
)
0.13
"The bioavailability of the four metabolites of metamizole (CAS 68-89-3), 4-methyl-amino-antipyrine (4-MAA), 4-formyl-amino-antipyrine (4-FAA), 4-amino-antipyrine (4-AA) and 4-acetyl-amino-antipyrine (4-AcAA) was compared after oral administration of a test (Analgin) and a reference formulation, both containing 1 g of metamizole."( Comparative bioavailability of two oral metamizole formulations. Influence of the acetylation phenotype.
Bacracheva, N; Drenska, A; Gorantcheva, J; Tyutyulkova, N; Vlahov, V, 1995
)
0.29
" This results in an increase in the rate of absorption of the active compound and, consequently, in an earlier onset of analgesic action."( Piroxicam-beta-cyclodextrin in the treatment of acute pain of rheumatic disease.
Franchimont, P; Reginster, JY, 1993
)
0.29
" Metamizol is well absorbed from the small intestine but only two above mentioned active metabolites and no parent drug can be detected in the blood."( [Metamizol--a new effective analgesic with a long history. Overview of its pharmacology and clinical use].
Fendrich, Z, 2000
)
0.31
" The results indicate that analgin nasal drops exhibited a higher bioavailability (relative to injection) and faster absorption (relative to tablet)."( [Studies on HPLC method for determination of 4-methylaminoantipyrine and relative bioavailabilities of analgin nasal drops in human volunteers].
Cui, JB; Jiang, XG; Xi, NZ, 1997
)
0.3
"The aim of this study was to investigate the extent and the rate of absorption of metamizole, appearing in blood as methylaminoantipyrine (MAA), from a new oral solution and a parenteral solution administered by the oral route relative to capsules."( Bioavailability of two metamizole (dipyrone) solutions as single doses of 2 g versus metamizole capsules.
Artaza, MA; Laporte, JR; Ortiz, R; Puerta, JL, 2002
)
0.31
" Metamizole as oral solution was bioequivalent to reference ampoules in the extent of MAA absorption, but absorption rate was faster."( Bioavailability of two metamizole (dipyrone) solutions as single doses of 2 g versus metamizole capsules.
Artaza, MA; Laporte, JR; Ortiz, R; Puerta, JL, 2002
)
0.31
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

Dipyrone, administered for 2 weeks, has effects on the gastric and duodenal mucosa comparable to those of paracetamol and placebo. noticeable damage is detectable at a dosage of 3 g/day.Increasing dipyrone dosage is a potential independent risk factor for AKI in adult ICU patients.

ExcerptRelevanceReference
"A simple, rapid, specific and sensitive colorimetric method is proposed for the quantitative estimation of noramido-pyrine methanesulfonate sodium in different dosage forms as well as in blood and urine samples."( Colorimetric assay of noramidopyrine methanesulfonate sodium in formulations and in blood and urine samples.
Diab, AH, 1977
)
0.26
" One of the surviving dogs treated with antipyretic was given the low disophenol dose and all the other survivors were given the medium disophenol dosage level."( Investigations of therapeutic measures for disophenol toxicosis in dogs.
Menhusen, MJ; Oehme, FW; Penumarthy, L, 1975
)
0.25
" A comparison between the single and the "cocktail" dosage did not reveal any significant differences in the pharmacokinetic parameters."( [Simultaneous administration of various model substances for characterizing in vivo biotransformation in chronic liver diseases].
Henschel, L; Hoffmann, A; Huster, A; Jorke, D; Kraul, H; Reinhardt, M; Töpfer, R; Truckenbrodt, J, 1990
)
0.28
" The efficacy of both drugs was judged by the physicians to be good or very good in 70% of cases and there were no statistically significant differences between the two treatment groups in the dosage required or the pain relief."( Pharmacokinetics and therapeutic study with nimesulide suppositories in children with post-operative pain and inflammation.
Brülhart, K; Monti, T; Schärli, AF,
)
0.13
" The trial was open, randomized, and cross-over, with a one-week interval between dosing days."( Pharmacokinetics of metamizol metabolites in healthy subjects after a single oral dose of metamizol sodium.
Bacracheva, N; Badian, M; Verho, M; Vlahov, V, 1990
)
0.28
" During thermal pain stimulation pymadine had the analgesic effect only at dosage of 5 mg/kg and potentiated the action of morphine given in doses of 3 and 5 mg/kg."( [Analgesic activity of pymadine].
Bantutova, I; Mitsov, V,
)
0.13
"5 g, the dose-response relationship of the analgesic effect has not been investigated in humans."( [Dose-dependence of the analgesic action of metamizol].
Neddermann, E; Rohdewald, P, 1988
)
0.27
" Tiapride dosage was brought down to four tablets per day."( [Detoxication of a drug-dependent patient (author's transl)].
Chancelade, C, 1982
)
0.26
" Areas under the curves from 1 to 6 h after dosing indicated distinct interindividual differences in metabolite patterns even in the absence of disturbed liver function, whereas the intraindividual data were closely reproducible."( Plasma levels of parent drug and metabolites in the intravenous aminopyrine breath test.
Breyer-Pfaff, U; Egberts, EH; Harder, M, 1982
)
0.26
" The results of the eight drugs revealed that ciliary movement is frequently affected by many drugs and, therefore, care must be taken in developing any nasal dosage form to ensure its least ciliotoxicity."( [Toxicity of drugs on nasal mucocilia and the method of its evaluation].
Cui, JB; Fang, XL; Jiang, XG; Wei, Y; Xi, NZ, 1995
)
0.29
" Dipyrone, administered for 2 weeks, has effects on the gastric and duodenal mucosa comparable to those of paracetamol and placebo, though noticeable damage is detectable at a dosage of 3 g/day."( Endoscopic assessment of the effects of dipyrone (metamizol) in comparison to paracetamol and placebo on the gastric and duodenal mucosa of healthy adult volunteers.
Ardizzone, S; Bianchi Porro, G; Caruso, I; Montrone, F; Petrillo, M, 1996
)
0.29
" upon diagnosis and half dosage once daily thereafter."( The anti-inflammatory drugs phenylbutazone and dipyrone in the treatment of field cases of bovine mastitis.
Saran, A; Shpigel, NY; Winkler, M; Ziv, G, 1996
)
0.29
" Diflunisal was given at the dosage of 500 mg perorally twice a day, and dipyrone was given at the dosage of 500 mg perorally three times a day."( A comparison of two nonsteroidal antiinflammatory drugs (diflunisal versus dipyrone) in the treatment of moderate to severe cancer pain: a randomized crossover study.
Firat, D; Güllü, IH; Savaş, C; Tekuzman, G; Yalçin, S, 1998
)
0.3
" The proposed method has been applied to the determination of these drugs in their each pharmaceutical dosage forms with satisfactory results."( Study on the charge-transfer reaction between 7,7,8,8-tetracyanoquinodimethane and drugs.
Bian-zhen, X; Feng-lin, Z; Shen-yang, T; Zhi-quan, Z, 1999
)
0.3
" Forty-three percent of the parents administered the recommended dosage (10-20 mg/kg), whereas 24."( Parental knowledge of the treatment of fever in children.
Barzilai, A; Davidovitch, N; Eisen, I; Kaplan, G; Linder, N; Sirota, L; Snapir, A, 1999
)
0.3
" Overall, patients in both groups requested only 25% of the permissible dosage of analgesia."( Oral analgesia in the treatment of post-cesarean pain.
Alpert, I; Itskovitz-Eldor, J; Jakobi, P; Solt, I; Weiner, Z; Zimmer, EZ, 2000
)
0.31
"Two accurate, precise and sensitive thin layer chromatographic (TLC) and second derivative UV-spectrophotometric procedures are described for the simultaneous determination of ascorbic acid and dipyrone in pure form and in pharmaceutical dosage forms."( Second derivative ultraviolet spectrophotometry and HPTLC for the simultaneous determination of vitamin C and dipyrone.
Abuirjeie, M; Aburjai, T; Aiedeh, K; al-Khalil, S; Amro, BI, 2000
)
0.31
" Dose-response curves (s."( Interaction between metamizol and tramadol in a model of acute visceral pain in rats.
Planas, E; Pol, O; Poveda, R; Puig, MM; Romero, A; Sánchez, S, 2003
)
0.32
"To assess clinical efficacy of IV paracetamol 1 g and IV metamizol 1 IV metamizol 1 g on a 24-h dosing schedule in this randomized, double-blinded, placebo-controlled study of 38 ASA physical status I-III patients undergoing retinal surgery."( A comparison between IV paracetamol and IV metamizol for postoperative analgesia after retinal surgery.
Eggert, D; Giesecke, T; Kampe, S; Kiencke, P; Landwehr, S; Thumann, G, 2005
)
0.33
" However, only a fractional amount of the applied dosage can be recovered by this procedure."( Characterization of oxalic acid derivatives as new metabolites of metamizol (dipyrone) in incubated hen's egg and human.
Daldrup, T; Kiefer, H; Matyja, M; Neugebauer, M; Tarbah, FA; Weber, H; Wessel, JC, 2006
)
0.33
" The following medications were randomly given to the patients who declared pain in the sixth hour after the operation: naproxen sodium, meloxicam, rofecoxib, paracetamol, dipyrone, and etodolac in proper dosage to form groups of 20 for each medication."( [Postoperative pain management in clinics of otolaryngology].
Cağici, CA; Calişkan, EE; Erkan, AN; Gencay, S; Ozlüoğlu, LN; Sener, M; Yavuz, H; Yilmaz, I; Yilmazer, C, 2006
)
0.33
"To assess clinical efficacy of IV paracetamol 1 g and IV dipyrone 1 g on a 24-h dosing schedule in this randomised, double-blinded study of 40 ASA I-III (American Society of Anesthesiologists classification of physical status) patients undergoing surgery for breast cancer."( Clinical equivalence of IV paracetamol compared to IV dipyrone for postoperative analgesia after surgery for breast cancer.
Dagtekin, O; Haussmann, S; Kampe, S; Kiencke, P; Landwehr, S; Paul, M; Pilgram, B; Warm, M, 2006
)
0.33
" Patients kept daily diaries and recorded pain scores and self hydrocodone dosing upon awakening, in the afternoon, and at bed time."( Effect of cigarette smoking on serum hydrocodone levels in chronic pain patients.
Ackerman, WE; Ahmad, M, 2007
)
0.34
" Moreover, whereas plasma concentration of morphine markedly decreased up to 4h (C(4h)) after subchronic administration of the opioid, multiple dosing of the morphine+metamizol combination produced an accumulation of the drug in plasma (P<0."( Effect of metamizol on morphine pharmacokinetics and pharmacodynamics after acute and subchronic administration in arthritic rats.
Cortés-Arroyo, AR; Domínguez-Ramírez, AM; López, JR; López-Muñoz, FJ; Y de la Peña, MH, 2010
)
0.36
" Piritramide dosage and incidence of side effects were not reduced."( Efficacy of intravenous paracetamol compared to dipyrone and parecoxib for postoperative pain management after minor-to-intermediate surgery: a randomised, double-blind trial.
Brodner, G; Cosanne, I; Ellger, B; Freise, H; Gogarten, W; Hahnenkamp, K; Huppertz-Thyssen, M; Van Aken, H; Wempe, C, 2011
)
0.37
"This casuistic reports on a 59-year-old pain patient taking normal dosage Tramadol as analgetic drug, who suffered from chronic dizziness leading to immobilisation for more than 9 months."( [Chronic dizziness in a pain patient--pharmacogenomic identification of tramadol as cause].
Barth, J; Eichhorn, A, 2010
)
0.36
" Additionally, systematic reviews of these placebo-controlled trials have failed to determine clinically meaningful dose-response effect."( Analgesic effectiveness of dipyrone (metamizol) for postoperative pain after herniorrhaphy: a randomized, double-blind, dose-response study.
Alvarez, HD; Chaparro, LE; Joaqui, W; Lezcano, W, 2012
)
0.38
"This trial shows a dose-response effect of 40 mg/kg over 15 mg/kg of intravenous dipyrone based on better movement-induced pain control, lower morphine consumption and fewer opioid-related side effects."( Analgesic effectiveness of dipyrone (metamizol) for postoperative pain after herniorrhaphy: a randomized, double-blind, dose-response study.
Alvarez, HD; Chaparro, LE; Joaqui, W; Lezcano, W, 2012
)
0.38
" A careful and slow adoption of dosage leads to more safety and tolerability."( [Pain in multimorbid internistic patients].
Schneider, D; Zimmerli, L, 2012
)
0.38
" Dose-response curves were constructed and the values of ED50 for treatment alone and combined were statistically compared."( Synergistic effect of the L-tryptophan and kynurenic acid with dipyrone or paracetamol in mice.
Carvalho, AM; de França Fonteles, MM; de Sousa, FC; Dias, ML; Freire, LV; Rios, ER; Rocha, NF, 2013
)
0.39
" The purpose of this study was to investigate the antinociceptive and constipation effects of tramadol and metamizole alone or in combination in rats and to discern among the types of drug interactions that exist using dose-response curves and an isobolographic analysis."( Enhancement of antinociception but not constipation by combinations containing tramadol and metamizole in arthritic rats.
Bravo, G; Déciga-Campos, M; Domínguez-Ramírez, AM; Guevara-López, U; López-Muñoz, FJ; Moreno-Rocha, LA, 2013
)
0.39
" PGE2-induced mechanical hyperalgesia was inhibited by dipyrone, 4-MAA, and 4-AA in a dose-response manner."( The analgesic effect of dipyrone in peripheral tissue involves two different mechanisms: neuronal K(ATP) channel opening and CB(1) receptor activation.
Athie, MC; Bonet, IJ; Dias, EV; dos Santos, GG; Parada, CA; Tambeli, CH; Teixeira, JM, 2014
)
0.4
" Patients were divided into 3 groups according to the dosage of postoperative intravenous-patient-controlled analgesia: paracetamol, dipyrone, or placebo."( Administration of paracetamol versus dipyrone by intravenous patient-controlled analgesia for postoperative pain relief in children after tonsillectomy.
Aribogan, A; Caliskan, E; Caylakli, F; Kocum, A; Sener, M; Yilmaz, I,
)
0.13
" For residents with scheduled medication, dosage and duration of use were analysed."( Pain medication in German nursing homes: a whole lot of metamizole.
Hoffmann, F; Schmiemann, G, 2016
)
0.43
"8%), the mean daily dosage was 1843 mg (interquartile range [IQR]: 1500-2250); 66."( Pain medication in German nursing homes: a whole lot of metamizole.
Hoffmann, F; Schmiemann, G, 2016
)
0.43
"Increasing dipyrone dosage is a potential independent risk factor for AKI in adult ICU patients and may prolong vasopressor therapy."( The use of dipyrone in the ICU is associated with acute kidney injury: A retrospective cohort analysis.
Buessecker, L; Gillmann, HJ; Leffler, A; Stueber, T, 2017
)
0.46
" It was pointed out that the proper evaluation of the efficiency of the release modification requires the examination of dosage forms as well as physical mixtures of API and excipient."( Dissolution studies of metamizole sodium and pseudoephedrine sulphate dosage forms - comparison and correlation of electronic tongue results with reference studies.
Cal, K; Ciosek-Skibińska, P; Wesoły, M; Wróblewski, W; Zabadaj, M, 2018
)
0.48
" This article presents different analgesic drugs, their mode of action, indications, dosage and adverse drug reactions."( [Pharmacological Basis of Pain Treatment].
Schüning, J; Schwarzer, A, 2018
)
0.48
"We analysed hospitalized patients who ingested ASA at least 30 min prior to metamizole (recommended dosing group, n = 15), metamizole prior or simultaneously with ASA (not recommended dosing group, n = 16) and patients with unknown or mixed intake (mixed dosing group, n = 5)."( Intake of aspirin prior to metamizole does not completely prevent high on treatment platelet reactivity.
Bertsche, T; Dietze, C; Gockel, I; Josten, C; Kaiser, T; Petros, S; Pfrepper, C; Remane, Y; Schiek, S, 2020
)
0.56
"Maximum AA-induced LTA prior to the intake of ASA was significantly lower and the rate of high on treatment platelet reactivity (HTPR) higher in the recommended compared with the not recommended dosing group (19."( Intake of aspirin prior to metamizole does not completely prevent high on treatment platelet reactivity.
Bertsche, T; Dietze, C; Gockel, I; Josten, C; Kaiser, T; Petros, S; Pfrepper, C; Remane, Y; Schiek, S, 2020
)
0.56
" Patients were stratified in groups according to their estimated glomerular filtration rate for drug dosing of vancomycin and meropenem."( Drug dosing using estimated glomerular filtration rate: Misclassification due to metamizole interference in a creatinine assay.
Bojko, L; Borato, DCK; Borges, CL; Dionísio, LM; Moss, MF; Ripka, GP, 2021
)
0.62
"During the validity of metamizole treatment, the stratification for drug dosing by the estimated glomerular filtration rate is not reliable if the creatinine measurement is done through dry chemistry."( Drug dosing using estimated glomerular filtration rate: Misclassification due to metamizole interference in a creatinine assay.
Bojko, L; Borato, DCK; Borges, CL; Dionísio, LM; Moss, MF; Ripka, GP, 2021
)
0.62
" For the in vivo uterotrophic assay, immature female rats (22-days-old) were treated daily by oral gavage for three days with different doses of dipyrone alone (50, 100, 200 mg/kg/day) and associated with three ethynylestradiol (EE) doses (1, 3 and 10 μg/kg/day), which were based on a dose-response curve experiment."( Uterotrophic and in vitro screening for (anti)estrogenic activity of dipyrone.
da Silva Amaral, BA; Gomes, C; Grechi, N; Martino-Andrade, AJ; Palu, G; Passoni, MT; Rülker, C; van Ravenzwaay, B, 2021
)
0.62
"The aim of this study is to assess the current situation in out of hospital pain management in Germany regarding the substances, indications, dosage and the delegation of the use of analgesics to emergency medical service (EMS) staff."( Application of analgesics in emergency services in Germany: a survey of the medical directors.
Scharonow, M; Scharonow, O; Vilcane, S; Weilbach, C, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (7)

RoleDescription
antipyreticA drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
antirheumatic drugA drug used to treat rheumatoid arthritis.
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
peripheral nervous system drugA drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
prodrugA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
cyclooxygenase 3 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antirheumatic drugA drug used to treat rheumatoid arthritis.
peripheral nervous system drugA drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
antipyreticA drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
prodrugA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
cyclooxygenase 3 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
pyrazoles
amino sulfonic acidAn organosulfonic acid containing one or more amino groups.
organic sodium salt
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency17.03900.177814.390939.8107AID2147
acetylcholinesteraseHomo sapiens (human)Potency50.19240.002541.796015,848.9004AID1347395; AID1347398
15-lipoxygenase, partialHomo sapiens (human)Potency18.85410.012610.691788.5700AID887
USP1 protein, partialHomo sapiens (human)Potency35.48130.031637.5844354.8130AID504865
GLI family zinc finger 3Homo sapiens (human)Potency6.81020.000714.592883.7951AID1259369
Microtubule-associated protein tauHomo sapiens (human)Potency31.09890.180013.557439.8107AID1460; AID1468
estrogen nuclear receptor alphaHomo sapiens (human)Potency1.78000.000229.305416,493.5996AID743069; AID743079
polyunsaturated fatty acid lipoxygenase ALOX12Homo sapiens (human)Potency12.58931.000012.232631.6228AID1452
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency8.91250.251215.843239.8107AID504327
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency18.85410.316212.765731.6228AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency18.85410.00638.235039.8107AID881
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency39.81070.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)IC50 (µMol)375.50000.00582.14107.9000AID1803034
Carbonic anhydrase 2Homo sapiens (human)IC50 (µMol)375.50000.00021.10608.3000AID1803034
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (112)

Assay IDTitleYearJournalArticle
AID1803034CA Enzyme Assay from Article 10.3109/14756366.2011.574130: \\Evaluation of in vitro effects of some analgesic drugs on erythrocyte and recombinant carbonic anhydrase I and II.\\2012Journal of enzyme inhibition and medicinal chemistry, Feb, Volume: 27, Issue:1
Evaluation of in vitro effects of some analgesic drugs on erythrocyte and recombinant carbonic anhydrase I and II.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1743185Antiinflammatory activity in rat model of carrageenan-induced paw edema assessed as inhibition of hind paw swelling at 15 mg/kg, ip measured after 1 hr relative to control2020European journal of medicinal chemistry, Dec-15, Volume: 208Multiple biological active 4-aminopyrazoles containing trifluoromethyl and their 4-nitroso-precursors: Synthesis and evaluation.
AID1237658Anti-nociceptive activity in ip dosed Swiss mouse assessed as inhibition of acetic acid-induced writhing dosed 40 mins before acetic acid injection and measured over 25 mins2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Synthesis and evaluation of the anti-nociceptive and anti-inflammatory activity of 4-aminoquinoline derivatives.
AID1743189Analgesic activity in rat assessed as prolongation of latency period at 15 mg/kg, ip measured after 1 hr by hot-plate test relative to control2020European journal of medicinal chemistry, Dec-15, Volume: 208Multiple biological active 4-aminopyrazoles containing trifluoromethyl and their 4-nitroso-precursors: Synthesis and evaluation.
AID1743186Antiinflammatory activity in rat model of carrageenan-induced paw edema assessed as inhibition of hind paw swelling at 15 mg/kg, ip measured after 3 hrs relative to control2020European journal of medicinal chemistry, Dec-15, Volume: 208Multiple biological active 4-aminopyrazoles containing trifluoromethyl and their 4-nitroso-precursors: Synthesis and evaluation.
AID1179420Antinociceptive effect in mouse assessed as inhibition of acetic acid-induced abdominal constriction at 100 uM/kg, po2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis and evaluation of novel dapsone-thalidomide hybrids for the treatment of type 2 leprosy reactions.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1237659Anti-nociceptive activity in ip dosed Swiss mouse assessed as inhibition of acetic acid-induced writhing dosed 40 mins before acetic acid injection and measured over 25 mins relative to control2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Synthesis and evaluation of the anti-nociceptive and anti-inflammatory activity of 4-aminoquinoline derivatives.
AID616797Antinociceptive activity in Swiss albino mouse assessed as reduction in acetic acid-induced abdominal constrictions at 100 umol/kg, po administered 1 hr before acetic acid challenge measured for 20 mins relative to control2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Design, synthesis, and pharmacological evaluation of novel hybrid compounds to treat sickle cell disease symptoms.
AID636241Prodrug activation in C57BL/6 mouse spleen assessed as formation of arachidonoyl-4-aminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID687418Antinociceptive activity in Swiss mouse inflammatory pain model assessed as reduction in hyperalgesia at 160 ug/paw dosed 45 mins before PGE2 dosing measured 3 hrs post PGE2 challenge2011Journal of natural products, Apr-25, Volume: 74, Issue:4
Mechanisms involved in the antinociceptive effects of 7-hydroxycoumarin.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1404802Antinociceptive activity in Swiss albino mouse assessed as decrease in number of acetic acid-induced abdominal constriction at 100 umol/kg, po pretreated for 1 hr followed by acetic-acid challenge for 10 mins measured for 20 mins relative to control2018European journal of medicinal chemistry, Jun-25, Volume: 154Discovery of phenylsulfonylfuroxan derivatives as gamma globin inducers by histone acetylation.
AID1377056Antinociceptive activity in dopamine-induced Swiss mouse model of mechanical hyperalgesia at 320 ng/paw administered as intraplantar injection pretreated for 15 mins followed by dopamine challenge after 3 hrs by Von Frey filament assay2017Journal of natural products, 06-23, Volume: 80, Issue:6
Naphthoquinones of Sinningia reitzii and Anti-inflammatory/Antinociceptive Activities of 8-Hydroxydehydrodunnione.
AID636242Prodrug activation in FAAH wild type C57BL/6 mouse brain assessed as formation of arachidonoyl-4-methylaminoantipyrin at 600 mg/kg, po administered daily measured after 48 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID636239Prodrug activation in C57BL/6 mouse CSF assessed as formation of arachidonoyl-4-aminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID454681Antinociceptive activity in Albino mouse assessed as inhibition of acetic acid-induced abdominal constriction at 100 umol/kg, po treated 1 hr before acetic acid challenge relative to control2009Bioorganic & medicinal chemistry, Sep-15, Volume: 17, Issue:18
Synthesis and analgesic profile of conformationally constrained N-acylhydrazone analogues: discovery of novel N-arylideneamino quinazolin-4(3H)-one compounds derived from natural safrole.
AID636236Prodrug activation in C57BL/6 mouse spleen assessed as formation of arachidonoyl-4-methylaminoantipyrin at 600 mg/kg, po administered daily measured after 48 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID636247Prodrug activation in FAAH knock out C57BL/6 mouse brain assessed as formation of arachidonoyl-4-aminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID636238Prodrug activation in C57BL/6 mouse CSF assessed as formation of arachidonoyl-4-aminoantipyrin at 600 mg/kg, po administered daily measured after 48 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID533819Antinociceptive activity in ip dosed Swiss mouse assessed as inhibition of acetic acid-induced abdominal contraction administered 30 mins before acetic acid challenge measured after 20 mins2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID649083Antiinflammatory activity in albino rat assessed as inhibition of carrageenan-induced paw edema at 100 umol/kg, po administered 1 hr before carrageenan challenge measured after 3 hrs by plethysmometric analysis relative to control2012Bioorganic & medicinal chemistry, Mar-15, Volume: 20, Issue:6
Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives.
AID533813Ratio of acetyl salicylic acid ID50 to compound ID50 for inhibition of acetic acid-induced abdominal contraction in ip dosed Swiss mouse2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives.
AID636235Prodrug activation in C57BL/6 mouse CSF assessed as formation of arachidonoyl-4-methylaminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID387097Antinociceptive activity against acetic acid-induced abdominal constrictions in ip dosed Swiss mouse pretreated 30 mins before acetic acid challenge2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity.
AID487925Analgesic activity in albino Wistar rat assessed as reaction time required for tail flicking at 25 mg/kg, po after 90 mins by tail-flick method (Rvb = 3.87 +/- 0.355 sec)2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety.
AID1377057Antinociceptive activity in dibutyryl cyclic AMP-induced Swiss mouse model of mechanical hyperalgesia at 320 ng/paw administered as intraplantar injection pretreated for 15 mins followed by dibutyryl cyclic AMP challenge after 3 hrs by Von Frey filament a2017Journal of natural products, 06-23, Volume: 80, Issue:6
Naphthoquinones of Sinningia reitzii and Anti-inflammatory/Antinociceptive Activities of 8-Hydroxydehydrodunnione.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID636246Prodrug activation in FAAH knock out C57BL/6 mouse brain assessed as formation of arachidonoyl-4-methylaminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID387103Antinociceptive activity against formalin-induced paw pain in ip dosed Swiss mouse pretreated 30 mins before formalin challenge assessed after 15 to 30 mins2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID363307Analgesic activity against formalin-induced neurogenic pain in albino mouse assessed as time spent on paw licking at 1500 umol/kg, sc administered 20 mins before formalin challenge assessed for 30 mins at 5 mins intervals2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: novel agents with analgesic and anti-inflammatory properties.
AID636243Prodrug activation in FAAH wild type C57BL/6 mouse brain assessed as formation of arachidonoyl-4-aminoantipyrin at 600 mg/kg, po administered daily measured after 48 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID704130Antinociceptive activity in Swiss albino mouse assessed as inhibition of acetic-acid induced abdominal constriction at 100 umol/kg, po administered 1 hr prior to acetic-acid challenge measured after 10 mins relative to vehicle-treated control2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Design, synthesis, and pharmacological evaluation of novel hybrid compounds to treat sickle cell disease symptoms. part II: furoxan derivatives.
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID487924Analgesic activity in albino Wistar rat assessed as reaction time required for tail flicking at 25 mg/kg, po after 60 mins by tail-flick method (Rvb = 4 +/- 0.360 sec)2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety.
AID363310Analgesic activity in albino mouse assessed as response latency at 1500 ug/ml, sc after 30 mins by hot plate method2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: novel agents with analgesic and anti-inflammatory properties.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID636237Prodrug activation in C57BL/6 mouse spleen assessed as formation of arachidonoyl-4-methylaminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID649080Analgesic activity in albino mouse assessed as inhibition of acetic acid-induced abdominal constriction at 100 umol/kg, po administered 1 hr before acetic acid challenge measured after 60 mins relative to control2012Bioorganic & medicinal chemistry, Mar-15, Volume: 20, Issue:6
Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID636244Prodrug activation in FAAH wild type C57BL/6 mouse brain assessed as formation of arachidonoyl-4-methylaminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID533814Ratio of metamizole ID50 to compound ID50 for inhibition of acetic acid-induced abdominal contraction in ip dosed Swiss mouse2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives.
AID1377055Antinociceptive activity in PGE2-induced Swiss mouse model of mechanical hyperalgesia at 320 ng/paw administered as intraplantar injection pretreated for 15 mins followed by PGE2 challenge after 3 hrs by Von Frey filament assay2017Journal of natural products, 06-23, Volume: 80, Issue:6
Naphthoquinones of Sinningia reitzii and Anti-inflammatory/Antinociceptive Activities of 8-Hydroxydehydrodunnione.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID363314Increase in locomotor activity in albino mouse assessed as number of crossing at 1000 umol/kg2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: novel agents with analgesic and anti-inflammatory properties.
AID387095Antinociceptive activity against acetic acid-induced abdominal constrictions in Swiss mouse assessed as maximal inhibition at 10 mg/kg, ip pretreated 30 mins before acetic acid challenge2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID454682Antinociceptive activity in po treated Albino mouse assessed as inhibition of acetic acid-induced abdominal constriction treated 1 hr before acetic acid challenge2009Bioorganic & medicinal chemistry, Sep-15, Volume: 17, Issue:18
Synthesis and analgesic profile of conformationally constrained N-acylhydrazone analogues: discovery of novel N-arylideneamino quinazolin-4(3H)-one compounds derived from natural safrole.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID387102Antinociceptive activity against formalin-induced paw pain in ip dosed Swiss mouse pretreated 30 mins before formalin challenge assessed after 0 to 5 mins2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity.
AID636240Prodrug activation in C57BL/6 mouse spleen assessed as formation of arachidonoyl-4-aminoantipyrin at 600 mg/kg, po administered daily measured after 48 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID533818Antinociceptive activity in Swiss mouse assessed as inhibition of acetic acid-induced abdominal contraction at 0.1 to 100 mg/kg, ip administered 30 mins before acetic acid challenge measured after 20 mins relative to control2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives.
AID636245Prodrug activation in FAAH wild type C57BL/6 mouse brain assessed as formation of arachidonoyl-4-aminoantipyrin at 600 mg/kg, po administered daily measured after 120 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID487923Analgesic activity in albino Wistar rat assessed as reaction time required for tail flicking at 25 mg/kg, po after 30 mins by tail-flick method (Rvb = 3.97 +/- 0.287 sec)2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID533817Antinociceptive activity in Swiss mouse assessed as inhibition of acetic acid-induced writhing at 10 mg/kg, ip administered 30 mins before acetic acid challenge measured after 20 mins relative to control2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives.
AID636234Prodrug activation in C57BL/6 mouse CSF assessed as formation of arachidonoyl-4-methylaminoantipyrin at 600 mg/kg, po administered daily measured after 48 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,532)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990493 (32.18)18.7374
1990's254 (16.58)18.2507
2000's319 (20.82)29.6817
2010's356 (23.24)24.3611
2020's110 (7.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 97.24

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index97.24 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index165.89 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (97.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials272 (16.15%)5.53%
Reviews0 (0.00%)6.00%
Reviews73 (4.33%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies217 (12.89%)4.05%
Observational0 (0.00%)0.25%
Observational14 (0.83%)0.25%
Other5 (100.00%)84.16%
Other1,108 (65.80%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (49)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
National, Multicenter, Randomized, Double-blind, Triple-dummy, Phase II Clinical Trial to Evaluate the Efficacy and Safety of Canadá Association in the Treatment of Chronic Pain [NCT05125978]Phase 20 participants (Actual)Interventional2026-09-30Withdrawn(stopped due to Strategy review)
National, Multicenter, Randomized, Double-blind, Triple-dummy, Phase II Clinical Trial to Evaluate the Efficacy and Safety of Tiradentes Association in the Treatment of Acute Pain [NCT04593329]Phase 20 participants (Actual)Interventional2023-03-31Withdrawn(stopped due to Strategy review)
Efficacy of Regional Analgesia Techniques (Quadratus Lumborum Block and Transversus Abdominis Plane Block) in Acute and Chronic Pain Treatment in Patients After Cesarean Delivery [NCT03244540]Phase 4105 participants (Actual)Interventional2017-09-04Completed
A Clinical, Multicenter, Randomized, Parallel-group, Double-blind, Double-dummy, Comparative Study of Non-inferiority of the Fixed Dose Combination of Codeine 30 mg/Dipyrone 500 mg From Eurofarma Versus Tylex® (Codeine 30 mg/Paracetamol 500 mg) in the Tre [NCT04972292]Phase 3288 participants (Anticipated)Interventional2023-11-08Recruiting
Effectiveness of Transversus Abdominis Plane Block Versus Quadratus Lumborum Technique in Patients After Cesarean Section [NCT02804126]Phase 4232 participants (Actual)Interventional2017-06-01Completed
A Randomized, Multicentre, Double-blind Clinical Trial of Metamizole 2 g /8 h, I.V. Ampoules, Versus Placebo Each 8 h, I.V. Ampoules, Administered During 3 Days Consecutively as Antithermic Therapy in the Acute Phase of Ischemic Stroke. A 30-day Study. (A [NCT02184260]Phase 458 participants (Actual)Interventional1998-12-31Terminated
Analgesic Effect of a New Metamizol Oral Pharmaceutical Form for the Treatment of the Neoplastic Chronic Pain: Randomized, Double-blind Crossover Clinical Trial Between Metamizol, Diclofenac and Placebo [NCT02181920]Phase 46 participants (Actual)Interventional2000-03-31Terminated
The Relationship Between Patient Preferences, Analgesic Delivery Method and Pain Reduction in Spine Patients [NCT01263652]0 participants (Actual)Interventional2010-12-31Withdrawn(stopped due to inability to complete recruitment as planned)
Randomized, Double Blind, Comparative Trial of the Efficacy and Tolerability of Nolotil i.v. vs. Placebo i.v. in the Prevention of Postoperative Pain in Children of 6 and 11 Years Old Undergoing Minor Surgery [NCT02184273]Phase 4122 participants (Actual)Interventional2002-03-31Completed
Influence of SPI-guided Analgesia With Preemptive Analgesia Using Either Paracetamol or Metamizole on the Presence of Oculocardiac Reflex, Postoperative Pain, Postoperative Nausea and Vomiting in Patients Undergoing VRS Under General Anaesthesia: a Random [NCT03389243]165 participants (Actual)Interventional2018-01-15Completed
Comparing Protocols for Analgesia Following Elective Cesarean Section [NCT03622489]Phase 4120 participants (Anticipated)Interventional2017-03-01Recruiting
Evaluation of the Added Value of Metamizole to Standard Post-operative Treatment After Ambulant Surgery: a Double-blind, Randomized, Controlled Trial [NCT04082728]110 participants (Actual)Interventional2019-11-28Completed
Migraine Abortive Treatment in Children and Adolescents in Israel [NCT05048914]50 participants (Anticipated)Observational2019-09-03Recruiting
Comparison Between Porcine Acellular Dermal Matrix (Mucoderm®) Versus Connective Tissue Graft in the Treatment of Multiple Adjacent Gingival Recessions Associated With Non-carious Cervical Lesion Partially Restored. [NCT03594513]50 participants (Actual)Interventional2018-07-02Active, not recruiting
A Randomised, Double Blind, Placebo- and Active-controlled Parallel Group Study Investigating the Efficacy and Tolerability of Metamizol 0.5 g and 1.0 g in Patients With Episodic Moderate Tension Headache. [NCT02183220]Phase 3417 participants (Actual)Interventional1998-10-31Completed
Interaction of Cytochrome P450 Inhibition With Metamizole Metabolism in Healthy Subjects [NCT04621253]Phase 112 participants (Actual)Interventional2020-04-29Completed
Randomized, Open Label, Comparative, Parallel, Multicenter Trial to Determinate the Efficacy Anf Tolerability of Ibuprofen, Acetaminophen and Dipyrone Drops to Fever Control in Children [NCT01359020]Phase 4396 participants (Actual)Interventional2007-01-31Completed
Optimal Timing of Endoscopic Intervention After Extracorporeal Shock-Wave Lithotripsy in the Treatment of Chronic Pancreatitis With Pancreatic Stones. [NCT05270434]225 participants (Anticipated)Interventional2022-03-01Not yet recruiting
Randomized, Double-blind, Placebo-controlled Single-centre Clinical Trial Evaluating Efficacy and Safety of Intraoperative and Postoperative Continuous Lidocaine Infusion in High Cardiac Risk Vascular Surgery [NCT04691726]Phase 487 participants (Actual)Interventional2019-01-29Completed
Ultrasound-Guided Bilateral Thoracic Paravertebral Blocks as an Adjunct to General Anaesthesia in Patients Undergoing Reduction Mammoplasty: A Historical Cohort Study [NCT02671851]64 participants (Actual)Observational2014-01-31Completed
Evaluation of the Added Value of Metamizole to Standard Postoperative Treatment After Ambulant Shoulder Surgery: a Double-blind, Randomized Controlled Trial [NCT04703257]110 participants (Actual)Interventional2021-02-26Completed
Effect of Metamizole on Renal Function in Salt-depleted Healthy Subjects Single-center, Randomized, Open, Controlled Parallel-group Study to Investigate the Effects of Oral Metamizole or Naproxen on Renal Function in Healthy Male Salt-depleted Subjects [NCT01995006]Phase 115 participants (Actual)Interventional2014-01-31Completed
A Multicenter Randomized Controlled Trial in Elderly Patients With Hip Fractures Comparing Continuous Fascia Iliaca Compartment Block to Systemic Opioids and Its Effect on Delirium Occurrence [NCT02689024]Phase 4239 participants (Actual)Interventional2016-05-31Terminated(stopped due to recruitment too slow; intervention was standard care in patients who were not included; acute care pathways changed due to policy regarding hip fracture patients)
Study of the Effect of Dipyrone, Ibuprofen, Paracetamol and Parecoxib on the Platelet Aggregation [NCT00763997]80 participants (Actual)Interventional2004-02-29Completed
Dipyrone Versus Acetaminophen in the Control of Postoperative Pain [NCT00841841]Phase 230 participants (Actual)Interventional2006-03-31Completed
Single-center, Open, Controlled Study to Investigate the Interaction of Metamizole With the Cytochrome p450 System in Healthy Subjects by Application of the Basel Cocktail [NCT03990129]Phase 112 participants (Actual)Interventional2018-09-04Completed
Single Center, Open-label, Prospective Study to Characterize the Pharmacokinetics of Metamizole and Its Metabolites Following Intravenous Administration in Children Less Than 6 Years Old [NCT02660177]Phase 233 participants (Actual)Interventional2016-04-30Completed
Potential Benefit of the Combination of Metamizole and Ibuprofen After Third Lower Molar Extraction [NCT02686021]Phase 436 participants (Actual)Interventional2016-02-15Completed
Postoperative Analgesia With Transversus Abdominis Plane Block or Quadratus Lumborum Block in Patients After Cesarian Delivery [NCT03404908]Phase 4105 participants (Actual)Interventional2018-02-07Completed
Optimal Analgesia in Acute Gastroenteritis in Emergency Department Setting: Dipyrone Versus Papaverine [NCT02711241]Phase 315 participants (Actual)Interventional2010-06-30Terminated(stopped due to Not enough patients)
National, Phase III, Multicenter, Randomized, Double-Blind, Parallel, Non-Inferiority Trial to Evaluate the Efficacy and Safety of Cefaliv® Compared to the Neosaldina® in the Treatment of Migraine Attacks [NCT02706015]Phase 30 participants (Actual)Interventional2020-10-31Withdrawn(stopped due to Strategic reasons of the company)
Double-blind, Randomized Controlled Study to Assess the Analgesic Effect of a Single Intravenous Dose of 2 g of Magnesium Dipyrone (Metamizol) and Changes in Plasma Beta-endorphin Immunoreactivity (Beta-EPIr) Values in Patients Undergoing Elective Inguina [NCT04595877]Phase 460 participants (Actual)Interventional2006-01-31Completed
Postoperative Pain After Laparoscopic Sleeve Gastrectomy: Comparison of Isolated Intravenous Analgesia, Epidural Analgesia Associated With Analgesia iv and Port-sites Infiltration With Bupivacaine Associated With Analgesia iv [NCT02662660]Phase 3147 participants (Actual)Interventional2012-01-31Completed
Efficacy of Metamizole Versus Ibuprofen and a Short Educational Intervention Versus Standard Care in Acute and Subacute Low Back Pain: A Randomized, Factorial Trial [NCT04111315]Phase 4120 participants (Anticipated)Interventional2019-12-15Recruiting
The Efficacy of Intravenous Paracetamol Versus Dipyrone for Postoperative Analgesia After Day-case Lower Abdominal Surgery in Children With Spinal Anesthesia: a Prospective Randomized Double-blind Study [NCT01858402]Phase 22 participants (Actual)Interventional2009-12-31Completed
Evaluation of Two Different Flaps Associated With Connective Tissue Graft in the Treatment of Gingival Recession: A Randomized Clinical Trial [NCT02814279]42 participants (Actual)Interventional2014-02-28Completed
Comparative, Randomized Trial of SPI-directed Intravenous Analgesia Using Metamizole With Tramadol Versus Preemptive Wound Infiltration Using 0,2 % Ropivacaine With Fentanyl or 0,2 % Bupivacaine With Fentanyl for Lumbar Discectomy [NCT02971540]132 participants (Actual)Interventional2016-02-29Completed
Evaluation of a New Surgical-restorative Approach for the Treatment of Gingival Recessions Associated With Non-carious Cervical Lesions: a Randomized Controlled Clinical Trial [NCT02817763]40 participants (Actual)Interventional2014-02-28Completed
Randomized, Open, Multicentre, National Superiority Clinical Trial to Assess the Combination of Fixed Dosage of Dipyrone and Codeine Compared to the Isolated Use of Components in the Control of Moderate to Severe Pain After Open Pelvic-abdominal Surgery. [NCT04641338]Phase 3328 participants (Anticipated)Interventional2023-03-16Recruiting
Use of Ibuprofen Versus Dipyrone in Preeclampsia Submitted to C-section: Randomized Clinical Trial [NCT05586373]Phase 474 participants (Actual)Interventional2022-10-15Completed
Valoración Del Dolor Postoperatorio en Pacientes Sometidos a craneotomía Programada [NCT04720248]73 participants (Actual)Observational2021-02-24Completed
Functionalization of a Volume-stable Collagen Matrix (VCMX) Using Injectable Platelet Rich Fibrin (i-PRF) for the Treatment of Single Gingival Recession [NCT05916742]75 participants (Anticipated)Interventional2022-04-15Recruiting
Diclofenac Premedication, as the Effect of Preemptive Analgesia After Post-thoracotomy Chest and Shoulder Pain, as Well as the Changes of the Postoperative Breathing Function Values, a Randomized, Controlled, Prospective Trial [NCT02445599]Phase 43 participants (Actual)Interventional2014-04-30Completed
Influence of Surgical Pleth Index-guided Analgesia Using Different Techniques on the Perioperative Outcomes in Patients Undergoing Vitreoretinal Surgery Under General Anaesthesia: Randomised, Controlled Trial [NCT02973581]176 participants (Actual)Interventional2016-02-29Completed
Post-operative Morphine Consumption in Obese Patients Undergoing Laparoscopic Bariatric Surgery Following Ketamina and Lidocaine Perfusion [NCT05591105]60 participants (Actual)Observational2022-01-15Completed
Use of a Novel Volume-stable Collagen Matrix (VCMX) in the Treatment of Single Gingival Recession Associated With Non-carious Cervical Lesion Partially Restored. A Randomized Clinical Trial [NCT05916716]50 participants (Anticipated)Interventional2022-08-01Recruiting
The Effect of Gabapentin Used as a Preemptive to the Emergence and Development Chronic Neuropathic Pain in Patients After Spinal Cord Trauma [NCT03255330]Phase 30 participants (Actual)Interventional2017-10-31Withdrawn(stopped due to no participant enrolled)
Randomized Controlled Trial to Evaluate the Efficiency of IV Fluids in the Treatment of Renal Colic [NCT03529097]Phase 40 participants (Actual)Interventional2018-06-01Withdrawn(stopped due to No participants enrolles)
Laparoscopic-guided Transversus Abdominis Plane (TAP) Block for Postoperative Pain Control in Patients Undergoing Laparoscopic Roux-en-Y Gastric Bypass [NCT03203070]Phase 3200 participants (Anticipated)Interventional2017-03-01Recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT02814279 (2) [back to overview]Percentage of Defect Coverage
NCT02814279 (2) [back to overview]Root Coverage Esthetic Score
NCT02817763 (2) [back to overview]Modified Root Coverage Esthetic Score (MRES)
NCT02817763 (2) [back to overview]Percentage of Defect Coverage

Percentage of Defect Coverage

Percentage mean (%) of root surface covered by the surgical treatment, measured through a periodontal probe. (NCT02814279)
Timeframe: 6 months

Interventionpercentage of root coverage (Mean)
CAF Plus Connective Tissue Graft87.2
Tunnel Plus Connective Tissue Graft77.4

[back to top]

Root Coverage Esthetic Score

The Root Coverage Esthetic Scale (RES; Cairo et al. 2009) was performed by two blinded and independent examiners (CFA and IFM) at the 6-month post-operative assessment. This score evaluates five variables: level of the gingival margin, marginal tissue contour, soft tissue texture, mucogingival junction alignment, and gingival color. Because complete root coverage was the primary treatment goal, and the other variables were considered secondary, the value assigned for root coverage was 60% of the total score, whereas 40% was assigned to the other four variables. With regard to the assessment of the final position of the gingival margin, 3 points were given for partial root coverage, and 6 points were given for complete root coverage; 0 points were assigned when the final position of the gingival margin was equal or apical to the previous recession. One point was assigned for each of the other four variables. Thus, 10 points was a perfect score. (NCT02814279)
Timeframe: 6 months

Interventionunits on a scale (Mean)
CAF Plus Connective Tissue Graft8.12
Tunnel Plus Connective Tissue Graft7.98

[back to top]

Modified Root Coverage Esthetic Score (MRES)

The MRES evaluated six variables: gingival margin (GM): 0 or 3 points; marginal tissue contour (MTC): 0 or 1 point; soft tissue texture (STT): 0 or 1 point; mucogingival junction alignment (MGJ): 0 or 1 point; gingival color (GC): 0 or 1 point; restoration/cervical lesion color (R/CLC): 0 points = color of restoration or uncovered cervical lesion does not match with tooth's color; 3 points = good color integration. Thus, 10 points was a perfect score. (NCT02817763)
Timeframe: 6 months

Interventionunits on a scale (Mean)
Connective Tissue Graft (CTG)7.13
CTG Plus Resin Composite Restoration8.71

[back to top]

Percentage of Defect Coverage

Percentage mean (%) of root surface covered by the surgical treatment, measured through a periodontal probe. (NCT02817763)
Timeframe: 6 months

InterventionGingival recessions (Count of Units)
Connective Tissue Graft (CTG)15
CTG Plus Resin Composite Restoration14

[back to top]