U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H12N2O
Molecular Weight 188.2262
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANTIPYRINE

SMILES

Cc1cc(=O)n(-c2ccccc2)n1C

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
PubMed

PubMed

TitleDatePubMed
The radiological diagnosis of analgesic nephropathy.
1975 Jul
[Insidious drug eruption].
2001
Clinical pharmacokinetics of quetiapine: an atypical antipsychotic.
2001
Impairment of metabolic function in chronic hepatitis C is related to factors associated with resistance to therapy.
2001 Aug
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
Schedule of controlled substances: placement of dichloralphenazone into Schedule IV. Final rule.
2001 Aug 16
A female with asymptomatic primary biliary cirrhosis associated with pernicious anemia.
2001 Dec
Determination of ototoxicity of common otic drops using isolated cochlear outer hair cells.
2001 Dec
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
Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines.
2001 Jun
Synthesis and antimicrobial activity of novel pyrazole, pyrazoline, pyrazolinone and pyrazolidinedione derivatives of benzimidazole.
2001 May-Jun
Polymeric transdermal drug penetration enhancer. The enhancing effect of oligodimethylsiloxane containing a glucopyranosyl end group.
2001 Nov 9
Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective.
2001 Nov-Dec
Phosphorylation of cyclic adenosine monophosphate response element binding protein in oligodendrocytes in the corpus callosum after focal cerebral ischemia in the rat.
2001 Oct
Theoretical considerations on the in vivo intestinal permeability determination by means of the single pass and recirculating techniques.
2001 Oct 23
Regioselective synthesis of polysubstituted pyrazoles and isoxazoles.
2001 Oct 5
Induction of hepatic and presystemic metabolism of antipyrine in the mice: rifampicin versus rifabutin.
2001 Oct-Dec
Ten-year combination treatment with colchicine and ursodeoxycholic acid for primary biliary cirrhosis: a double-blind, placebo-controlled trial on symptomatic patients.
2001 Sep
Automated structural assignment of derivatized complex N-linked oligosaccharides from tandem mass spectra.
2002
[Absorption function of the large intestine in patients with nonspecific ulcerative colitis].
2002
Migraine, Midrin, and Imitrex.
2002 Apr
Enzyme and plasma protein induction by multiple oral administrations of phenobarbital at a therapeutic dosage regimen in dogs.
2002 Apr
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion 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
Evaluation of the anti-vascular effects of combretastatin in rodent tumours by dynamic contrast enhanced MRI.
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
Albendazole metabolism in patients with neurocysticercosis: antipyrine as a multifunctional marker drug of cytochrome P450.
2002 Feb
Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170.
2002 Jan
Rational determination of transfer free energies of small drugs across the water-oil interface.
2002 Jan 3
Effect of mild hypothermia on energy state recovery following transient forebrain ischemia in the gerbil.
2002 Jul
A study of immunoglobulin G glycosylation in monoclonal and polyclonal species by electrospray and matrix-assisted laser desorption/ionization mass spectrometry.
2002 Jun 1
Estimation of intradermal disposition kinetics of drugs: II. Factors determining penetration of drugs from viable skin to muscular layer.
2002 Jun 4
Influence of albumin supplementation on tacrolimus and cyclosporine therapy early after liver transplantation.
2002 Mar
Auto-protective redox buffering systems in stimulated macrophages.
2002 Mar 12
Probucol and liver efficiency during chemically-induced hepatocarcinogenesis.
2002 Mar-Apr
[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
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
ANTIPYRINE [USP-RS]
Common Name English
ANTIPYRINE [VANDF]
Common Name English
PHENAZONE [MART.]
Common Name English
PHENAZONE [EP MONOGRAPH]
Common Name English
ANTIPYRINUM
HPUS  
Common Name English
ANTIPYRINE [USP]
Common Name English
PHENAZONE [EP]
Common Name English
ANTIPYRINUM [HPUS]
Common Name English
PHENAZONE [INN]
Common Name English
PHENAZONE
EP   INN   MART.   WHO-DD  
INN  
Official Name English
PHENAZONE [WHO-DD]
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 Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
NCI_THESAURUS C257
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
WHO-ATC N02BB71
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
WHO-VATC QS02DA03
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
FDA ORPHAN DRUG 5284
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
WHO-VATC QN02BB01
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
WHO-ATC N02BB01
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
WHO-VATC QN02BB51
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
WHO-VATC QN02BB71
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
WHO-ATC N02BB51
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
Code System Code Type Description
MERCK INDEX
M1973
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY Merck Index
EPA CompTox
60-80-0
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
DRUG BANK
DB01435
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
FDA UNII
T3CHA1B51H
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
MESH
D000983
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
RXCUI
1001
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY RxNorm
PUBCHEM
2206
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
CAS
60-80-0
Created by admin on Fri Jun 25 20:58:38 UTC 2021 , Edited by admin on Fri Jun 25 20:58:38 UTC 2021
PRIMARY
DRUG CENTRAL
861
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
ChEMBL
CHEMBL277474
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
INN
413
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
WIKIPEDIA
PHENAZONE
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
LACTMED
Antipyrine
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
USP_CATALOG
1040005
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY USP-RS
NCI_THESAURUS
C76794
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
EVMPD
SUB09753MIG
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-486-6
Created by admin on Fri Jun 25 20:58:39 UTC 2021 , Edited by admin on Fri Jun 25 20:58:39 UTC 2021
PRIMARY