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Details

Stereochemistry ACHIRAL
Molecular Formula C11H12N2O
Molecular Weight 188.2258
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANTIPYRINE

SMILES

CN1N(C(=O)C=C1C)C2=CC=CC=C2

InChI

InChIKey=VEQOALNAAJBPNY-UHFFFAOYSA-N
InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3

HIDE SMILES / InChI

Molecular Formula C11H12N2O
Molecular Weight 188.2258
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. It inhibits cyclooxygenases and shows little anti-inflammatory activity. Like many old and approved substances after almost 100 years of use, antipyrine has been associated with some serious side effects, namely agranulocytosis and shock reactions.

Originator

Sources: DOI: 10.1016/S1366-0071(97)80033-2

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Finoten

Approved Use

Antipyrine is indicated for local symptomatic treatment and relief of pain in the following diseases of the middle ear without tympanic perforation: acute, congestive otitis media; otitis in influenza, the so-called viral bullous otitis; barotraumatic otitis.
Palliative
Unknown

Approved Use

Unknown
Primary
Antipyrine

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.7 h
18 mg/kg single, oral
dose: 18 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANTIPYRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
13.8 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ANTIPYRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.97%
18 mg/kg single, oral
dose: 18 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANTIPYRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 50 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >1000 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no
weak [Inhibition 100 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Dissociation of brain edema induced by cold injury in rat model: MR imaging and perfusion studies with 14C-iodo-antipyrine.
2001 Aug
Impairment of metabolic function in chronic hepatitis C is related to factors associated with resistance to therapy.
2001 Aug
Exercise-induced oxidative stress in older adults as measured by antipyrine oxidation.
2001 Dec
Derivative ratio spectra-zero crossing spectrophotometry and LC method applied to the quantitative determination of paracetamol, propyphenazone and caffeine in ternary mixtures.
2001 Dec
The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides.
2001 Feb
Efficacy of naturopathic extracts in the management of ear pain associated with acute otitis media.
2001 Jul
Simultaneous measurement of cerebral blood flow and mRNA signals: pixel-based inter-modality correlational analysis.
2001 Jul 30
Synthesis of some triazolyl-antipyrine derivatives and investigation of analgesic activity.
2001 Jul-Aug
[Effect of hypoxic stress on xenobiotic metabolism and activities of various isoforms of cytochrome P-450].
2001 Jul-Aug
Metabolic functions of the liver during chemotherapy in children with acute lymphoblastic leukemia.
2001 Jun
Direct nuclear magnetic resonance spectroscopic analysis of (13)C-labeled antipyrine metabolites in human urine.
2001 Jun
Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process.
2001 May
In vitro and in vivo evaluation of an oral system for time and/or site-specific drug delivery.
2001 May 18
Synthesis and antimicrobial activity of novel pyrazole, pyrazoline, pyrazolinone and pyrazolidinedione derivatives of benzimidazole.
2001 May-Jun
Antioxidant supplementation and exercise-induced oxidative stress in the 60-year-old as measured by antipyrine hydroxylates.
2001 Nov
Phosphorylation of cyclic adenosine monophosphate response element binding protein in oligodendrocytes in the corpus callosum after focal cerebral ischemia in the rat.
2001 Oct
Regioselective synthesis of polysubstituted pyrazoles and isoxazoles.
2001 Oct 5
Ten-year combination treatment with colchicine and ursodeoxycholic acid for primary biliary cirrhosis: a double-blind, placebo-controlled trial on symptomatic patients.
2001 Sep
Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration.
2002
[Absorption function of the large intestine in patients with nonspecific ulcerative colitis].
2002
Synthesis of syn and anti isomers of trans-cyclopropyl arginine.
2002 Apr 5
Determination of oligosaccharides in Pompe disease by electrospray ionization tandem mass spectrometry.
2002 Jan
4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamidinium acetate acetone hemisolvate.
2002 Jul
Effect of mild hypothermia on energy state recovery following transient forebrain ischemia in the gerbil.
2002 Jul
Diabetes and elimination of antipyrine in man: an analysis of 298 patients classified by type of diabetes, age, sex, duration of disease and liver involvement.
2002 Mar
Combined argatroban and edaravone caused additive neuroprotection against 15 min of forebrain ischemia in gerbils.
2002 May
[Pharmacological and clinical profile of the free radical scavenger edaravone as a neuroprotective agent].
2002 May
Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro.
2002 May
A new method for measuring oxidative stress in claudicants during strenuous exercise using free radical derivatives of antipyrine as indicators: a pilot study.
2002 Spring
Patents

Sample Use Guides

54 mg apply drops along the wall of the ear canal until filled and repeating every 3 hours for 24 hours unless the subject is sleeping.
Route of Administration: Otic (auricular)
In Vitro Use Guide
The influence of phenazone on the production of prostacyclin and thromboxane in human umbilical arteries was investigated by in vitro perfusion. With perfusate concentrations ranging from 10(-7) to 10(-4) M a decrease in the formation of both prostanoids was observed. The inhibitory effect of phenazone on prostanoid formation was found to be equal to that of indomethacin.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:13 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:13 GMT 2025
Record UNII
T3CHA1B51H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTIPYRINE
II   MI   USP   USP-RS   VANDF  
Common Name English
PHENAZONE
EP   INN   MART.   WHO-DD  
INN  
Preferred Name English
ANTIPYRINE [USP-RS]
Common Name English
ANTIPYRINE [VANDF]
Common Name English
PHENAZONE [EP IMPURITY]
Common Name English
PHENAZONE [MART.]
Common Name English
PHENAZONE [EP MONOGRAPH]
Common Name English
Phenazone [WHO-DD]
Common Name English
ANTIPYRINUM
HPUS  
Common Name English
2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one
Systematic Name English
ANTIPYRINE [USP IMPURITY]
Common Name English
ANTIPYRINUM [HPUS]
Common Name English
phenazone [INN]
Common Name English
PROPYPHENAZONE IMPURITY A [EP IMPURITY]
Common Name English
ANTIPYRINE [JAN]
Common Name English
ANTIPYRINE [USP MONOGRAPH]
Common Name English
ANTIPYRINE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC S02DA03
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
WHO-ATC N02BB71
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
WHO-VATC QS02DA03
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
FDA ORPHAN DRUG 5284
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
WHO-VATC QN02BB01
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
WHO-ATC N02BB01
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
WHO-VATC QN02BB51
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
WHO-VATC QN02BB71
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
WHO-ATC N02BB51
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
Code System Code Type Description
CHEBI
31225
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
MERCK INDEX
m1973
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID6021117
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
DRUG BANK
DB01435
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
FDA UNII
T3CHA1B51H
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
MESH
D000983
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
RXCUI
1001
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY RxNorm
PUBCHEM
2206
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
CAS
60-80-0
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
DAILYMED
T3CHA1B51H
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
DRUG CENTRAL
861
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
RS_ITEM_NUM
1040005
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL277474
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
INN
413
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
WIKIPEDIA
PHENAZONE
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
LACTMED
Antipyrine
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
NCI_THESAURUS
C76794
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
EVMPD
SUB09753MIG
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
SMS_ID
100000085208
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-486-6
Created by admin on Mon Mar 31 17:33:13 GMT 2025 , Edited by admin on Mon Mar 31 17:33:13 GMT 2025
PRIMARY
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METABOLIC ENZYME -> SUBSTRATE
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