U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
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
[Insidious drug eruption].
2001
[Changes in the immune status parameters and their correction in various forms of tick-borne encephalitis].
2001
Clinical pharmacokinetics of quetiapine: an atypical antipsychotic.
2001
Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine.
2001 Apr
Lack of hypercapnic increase in cerebral blood flow at high blood viscosity in conscious blood-exchanged rats.
2001 Aug
An autoradiographic study of regional blood flow distribution in the rat kidney during ureteric obstruction--the role of vasoactive compounds.
2001 Aug
Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter.
2001 Dec
Exercise-induced oxidative stress in older adults as measured by antipyrine oxidation.
2001 Dec
The effects of uterine and umbilical blood flows on the transfer of propofol across the human placenta during in vitro perfusion.
2001 Jul
Simultaneous measurement of cerebral blood flow and mRNA signals: pixel-based inter-modality correlational analysis.
2001 Jul 30
Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines.
2001 Jun
Metabolic functions of the liver during chemotherapy in children with acute lymphoblastic leukemia.
2001 Jun
Capillary electrophoretic analysis of carbohydrates derivatized by in-capillary condensation with 1-phenyl-3-methyl-5-pyrazolone.
2001 Mar 16
Metabolic capacity and interindividual variation in toxicokinetics of styrene in volunteers.
2001 May
Investigation of different combinations of derivatization, separation methods and electrospray ionization mass spectrometry for standard oligosaccharides and glycans from ovalbumin.
2001 May
Effects of 4-hydroxyantipyrine and its 4-O-sulfate on antipyrine as biodistribution promoter.
2001 May
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
Combined effects of acetaminophen, isopropylantipyrine and caffeine on pregnant and nonpregnant liver.
2001 Nov
Antioxidant supplementation and exercise-induced oxidative stress in the 60-year-old as measured by antipyrine hydroxylates.
2001 Nov
Placental transfer of SR49059 in the human dually perfused cotyledon in vitro.
2001 Nov
Exercise training and oxidative stress in the elderly as measured by antipyrine hydroxylation products.
2001 Oct
Automated structural assignment of derivatized complex N-linked oligosaccharides from tandem mass spectra.
2002
Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration.
2002
The onset of action and the analgesic efficacy of Saridon (a propyphenazone/paracetamol/ caffeine combination) in comparison with paracetamol, ibuprofen, aspirin and placebo (pooled statistical analysis).
2002
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans.
2002 Apr
Acute hypoxia and cytochrome P450-mediated hepatic drug metabolism in humans.
2002 Apr
The effect of amiloride on the in vivo effective permeability of amoxicillin in human jejunum: experience from a regional perfusion technique.
2002 Apr
Synthesis of syn and anti isomers of trans-cyclopropyl arginine.
2002 Apr 5
The concordance of early antipyrine and thiopental distribution kinetics.
2002 Aug
Prediction of hepatic clearance and availability by cryopreserved human hepatocytes: an application of serum incubation method.
2002 Aug
Effect of the free radical scavenger, 3-methyl-1-phenyl-2-pyrazolin-5-one (MCI-186), on hypoxia-ischemia-induced brain injury in neonatal rats.
2002 Aug 23
Exercise-induced oxidative stress in older adults as a function of habitual activity level.
2002 Feb
Transplacental transfer and metabolism of buprenorphine.
2002 Jan
Determination of oligosaccharides in Pompe disease by electrospray ionization tandem mass spectrometry.
2002 Jan
Rational determination of transfer free energies of small drugs across the water-oil interface.
2002 Jan 3
A study of immunoglobulin G glycosylation in monoclonal and polyclonal species by electrospray and matrix-assisted laser desorption/ionization mass spectrometry.
2002 Jun 1
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
Influence of albumin supplementation on tacrolimus and cyclosporine therapy early after liver transplantation.
2002 Mar
Effect of growth hormone on hepatic cytochrome P450 activity in healthy elderly men.
2002 Mar
Auto-protective redox buffering systems in stimulated macrophages.
2002 Mar 12
Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro.
2002 May
Next generation of everyday analgesics.
2002 May-Jun
An implantable bolus infusion pump for use in freely moving, nontethered rats.
2002 Oct
Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs, and monkeys.
2002 Oct
Direct analysis of nine pharmaceuticals in culture media by use of cartridge separation with electrospray mass spectrometric detection.
2002 Sep
Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats.
2002 Sep 13
Myocardial protection of MCI-186 in rabbit ischemia-reperfusion.
2002 Sep 27
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.
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