Compounds > 4-formylaminoantipyrine
Page last updated: 2024-12-06

4-formylaminoantipyrine

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

Description

4-formylaminoantipyrine is a derivative of antipyrine, a nonsteroidal anti-inflammatory drug (NSAID). It has been synthesized via formylation of antipyrine using formic acid and acetic anhydride. Studies have shown that 4-formylaminoantipyrine exhibits analgesic and antipyretic activities, similar to antipyrine. Its importance lies in its potential as a lead compound for developing new NSAIDs with improved pharmacological profiles. Research on this compound is focused on understanding its mechanism of action, exploring its therapeutic potential, and optimizing its synthesis and properties.'

4-formylaminoantipyrine: metabolite of aminopyrine in man [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-formylaminoantipyrine : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a formaylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It is a metabolite of aminophenazone. [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 CID72666
CHEBI ID83526
SCHEMBL ID6812409
MeSH IDM0057406

Synonyms (54)

Synonym
HMS1673G16
formamide, n-antipyrinyl-
nsc-60565
1672-58-8
nsc60565
wln: t5nnvj a1 br& dmvh e1
formamide,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)-
AG-690/12869770
1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-ylformamide
OPREA1_056999
OPREA1_347608
4-formylaminoantipyrine
n-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)formamide
STK993651
n-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)formamide
AKOS000633307
nsc 60565
n-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)formamide
einecs 216-808-3
unii-63dku1m0xk
63dku1m0xk ,
n-antipyrinylformamide
4-formylamino antipyrine
4-formamidoantipyrine
4-(formylamino)antipyrine
FT-0648425
(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)formamide
SCHEMBL6812409
CHEBI:83526
n-antipyrinyl formamide
J61.595A ,
W-109692
n-(2,3-2h-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)formamide
DTXSID10168241
4-(formylamino)-1-phenyl-2,3-dimethyl-1h-pyrazole-5(2h)-one
metamizole sodium monohydrate impurity a [ep impurity]
formamide, n-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)-
metamizole impurity a
mfcd00085457
4-formylaminoantipyrine, vetranal(tm), analytical standard
HY-133588
CS-0128286
metamizole impurity a, european pharmacopoeia (ep) reference standard
4-formylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazol-3-one (4-formylaminophenazone)
n-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4- yl)formamide
4-faa
Q27156916
4formylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
WSJBSKRPKADYRQ-UHFFFAOYSA-N
DS-15213
4-formylaminoantipyrine 100 microg/ml in acetonitrile
C73223
4-carboxamido-1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazole-3-one
F1289

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" 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

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

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

Roles (2)

RoleDescription
marine xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
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
pyrazoloneA member of the class of pyrazoles in which one of the carbons of the pyrazole ring is substituted by an oxo group.
formamidesAmides with the general formula R(1)R(2)NCHO (R(1) and R(2) can be H).
[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 (2)

Assay IDTitleYearJournalArticle
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (44.00)18.7374
1990's6 (24.00)18.2507
2000's3 (12.00)29.6817
2010's5 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.30

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

MetricThis Compound (vs All)
Research Demand Index20.30 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (12.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (12.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (76.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
3-methylcholanthrene
Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.		2.3720ortho- and peri-fused polycyclic arenearyl hydrocarbon receptor agonist;
carcinogenic agent
acetaminophen
Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.		2.3720acetamides;
phenols		antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
cyclooxygenase 3 inhibitor;
environmental contaminant;
ferroptosis inducer;
geroprotector;
hepatotoxic agent;
human blood serum metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
ampyrone
Ampyrone: A metabolite of AMINOPYRINE with analgesic and anti-inflammatory properties. It is used as a reagent for biochemical reactions producing peroxides or phenols. Ampyrone stimulates LIVER MICROSOMES and is also used to measure extracellular water.		6.59193primary amino compound;
pyrazolone		antipyretic;
antirheumatic drug;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
marine xenobiotic metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
peripheral nervous system drug
antipyrine
Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.		4.0531pyrazoloneantipyretic;
cyclooxygenase 3 inhibitor;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		2.3720benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
furosemide
Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.		1.9610chlorobenzoic acid;
furans;
sulfonamide		environmental contaminant;
loop diuretic;
xenobiotic
ibuprofen
Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine		1.9610monocarboxylic acidantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
environmental contaminant;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
radical scavenger;
xenobiotic
propyphenazone
propyphenazone: structure. propyphenazone : A pyrazolone derivative that is antipyrine substituted at C-4 by an isopropyl group.		1.9710pyrazolonenon-narcotic analgesic;
non-steroidal anti-inflammatory drug;
peripheral nervous system drug
metyrapone
Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.		1.9710aromatic ketoneantimetabolite;
diagnostic agent;
EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
phenobarbital
Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.		2.3720barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
aminopyrine
Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.		6.77233pyrazolone;
tertiary amino compound		antipyretic;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
noramidopyrine
noramidopyrine: RN given refers to parent cpd; structure. 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.		6.53183pyrazoles;
secondary amino compound		antipyretic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
opioid analgesic;
peripheral nervous system drug
n-acetylaminoantipyrine
4-acetamidoantipyrine : A member of the class of pyrazoles that is antipyrine substituted by an acetylamino group at position 4. It is a drug metabolite of metamizole.		6.23133acetamides;
pyrazoles		drug metabolite;
marine xenobiotic metabolite
dipyrone
Dipyrone: A drug that has analgesic, anti-inflammatory, and antipyretic properties. It is the sodium sulfonate of AMINOPYRINE.. 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.		6.63203organic sodium saltanti-inflammatory agent;
antipyretic;
antirheumatic drug;
cyclooxygenase 3 inhibitor;
non-narcotic analgesic;
peripheral nervous system drug;
prodrug
morphine
Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.		2.0710morphinane alkaloid;
organic heteropentacyclic compound;
tertiary amino compound		anaesthetic;
drug allergen;
environmental contaminant;
geroprotector;
mu-opioid receptor agonist;
opioid analgesic;
plant metabolite;
vasodilator agent;
xenobiotic
clinoptilolite
clinoptilolite: clinoptilolite was SY to zeolite (NM); use zeolites (NM) to search through 1993; RN is for cpd with unknown MF		2.1510
zeolites
[no description available]		2.1510
ConditionIndicatedRelationship StrengthStudiesTrials
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Anaphylactic Reaction
[description not available]		02.1310
Anaphylaxis
An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.		02.1310
Acute Liver Injury, Drug-Induced
[description not available]		02.0110
Bile Duct Obstruction, Intrahepatic
[description not available]		02.0110
Allergy, Drug
[description not available]		02.0110
Cholestasis, Intrahepatic
Impairment of bile flow due to injury to the HEPATOCYTES; BILE CANALICULI; or the intrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC).		02.0110
Drug Hypersensitivity
Immunologically mediated adverse reactions to medicinal substances used legally or illegally.		02.0110
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.0110