Page last updated: 2024-12-05

noramidopyrine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Noramidopyrine is a synthetic compound structurally related to aminopyrine, a non-steroidal anti-inflammatory drug (NSAID). It is a potent analgesic and antipyretic, but it has also been found to have significant adverse effects, including agranulocytosis (a serious condition characterized by a deficiency of white blood cells). Its synthesis involves various chemical steps, including the reaction of aminopyrine with a suitable oxidizing agent. The effects of noramidopyrine are primarily related to its ability to inhibit the production of prostaglandins, which are involved in pain and inflammation. Due to its adverse effects, noramidopyrine is no longer widely used clinically. However, it remains an important compound for research purposes, as it provides insights into the mechanism of action of NSAIDs and the development of safer alternatives.'

noramidopyrine: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-(methylamino)antipyrine : A member of the class of pyrazoles that is antipyrine substituted at C-4 by a methylamino group. It is a metabolite of aminopyrine and of metamizole. [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 CID10618
CHEMBL ID1164701
CHEBI ID73261
SCHEMBL ID537958
MeSH IDM0052714

Synonyms (57)

Synonym
4-methylaminophenazone
n-methylaminoantipyrine
1,2-dihydro-1,5-dimethyl-4-(methylamino)-2-phenyl-3h-pyrazol-3-one
4-(methylamino)antipyrine
4-monomethylaminophenazone
noraminopyrine
einecs 208-281-3
monomethylaminoantipyrine
methylaminophenazone
brn 0195234
n-methylaminophenazone
4-monomethylaminoantipyrine
noramidopyrine
methylaminoantipyrine
1,5-dimethyl-4-(methylamino)-2-phenyl-2,3-dihydro-1h-pyrazol-3-one
3h-pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-4-(methylamino)-2-phenyl-
antipyrine, 4-(methylamino)-
OPREA1_672076
C15913
CHEMDIV2_002661
AKOS003342430
HMS1376I21
1,5-dimethyl-4-(methylamino)-2-phenylpyrazol-3-one
n-methyl-4-aminoantipyrine
4-methylaminoantipyrine
CHEMBL1164701 ,
chebi:73261 ,
STK735134
1,5-dimethyl-4-(methylamino)-2-phenyl-1,2-dihydro-3h-pyrazol-3-one
519-98-2
bdbm50360021
unii-ner31de951
n.a.p.
ner31de951 ,
4-methylamino antipyrine
FT-0648610
SCHEMBL537958
noramidopyrine [who-dd]
1,5-dimethyl-4-methylamino-2-phenyl-1,2-dihydro-3h-pyrazol-3-one
n-methyl-4-aminophenazone
metamizole sodium monohydrate impurity c [ep impurity]
1,5-dimethyl-4-(methylamino)-2-phenyl-1,2-dihydro-3h-pyrazol-3-one #
J-503822
4-(n-methyl)-aminoantipyrine
DTXSID80199865
4-(methylamino)-antipyrine
n-desmethylaminopyrine
Q27140411
HY-135731
2,3-dimethyl-4-monomethylamino-1-phenyl-3-pyrazolin5-one
FS-5885
CS-0113885
4-(methylamino)antipyrine 100 microg/ml in acetonitrile
EN300-10377497
B0337-466650
mfcd00447796
PD127426

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" 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

Pharmacokinetics

ExcerptReferenceRelevance
" 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
" 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
" 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
"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
"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

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
" 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

Dosage Studied

ExcerptRelevanceReference
" 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
" 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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (7)

RoleDescription
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
opioid analgesicA narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
non-steroidal anti-inflammatory drugAn anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitorA compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
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.
drug metabolitenull
[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 (2)

ClassDescription
pyrazoles
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
[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]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID636251Inhibition of COX-1 in C57BL/6 mouse brain homogenate2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID636252Inhibition of COX-2 in C57BL/6 mouse brain homogenate2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Novel bioactive metabolites of dipyrone (metamizol).
AID486711Antioxidant activity assessed as hydroxyl radical scavenging activity at 10 mM at pH 7 by fenton reaction2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Scavenging activity of aminoantipyrines against hydroxyl radical.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (79)

TimeframeStudies, This Drug (%)All Drugs %
pre-199042 (53.16)18.7374
1990's16 (20.25)18.2507
2000's7 (8.86)29.6817
2010's11 (13.92)24.3611
2020's3 (3.80)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 42.40

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index42.40 (24.57)
Research Supply Index4.56 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index61.96 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (42.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (14.46%)5.53%
Reviews0 (0.00%)6.00%
Case Studies7 (8.43%)4.05%
Observational0 (0.00%)0.25%
Other64 (77.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]