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
Molecular Formula C11H12N2O
Molecular Weight 188.2262
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Knorr, L.
4
Sources: DOI: 10.1016/S1366-0071(97)80033-2

Approval Year

1885
1
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
Inhibitor
7728
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8043
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
Phase II
1101
Unknown

Approved Use

Unknown
Primary
Not Provided
492
Antipyrine

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The radiological diagnosis of analgesic nephropathy.
1975 Jul
[Insidious drug eruption].
2001
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
Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter.
2001 Dec
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes.
2001 Jan-Feb
Combined effects of acetaminophen, isopropylantipyrine and caffeine on pregnant and nonpregnant liver.
2001 Nov
[Optimal conditions for extraction of "caffetin" and "saridon" tablet components from aqueous solutions].
2001 Nov-Dec
Induction of hepatic and presystemic metabolism of antipyrine in the mice: rifampicin versus rifabutin.
2001 Oct-Dec
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
[Absorption function of the large intestine in patients with nonspecific ulcerative colitis].
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
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
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
Albendazole metabolism in patients with neurocysticercosis: antipyrine as a multifunctional marker drug of cytochrome P450.
2002 Feb
Effects of prenatal exposure to combination of acetaminophen, isopropylantipyrine and caffeine on intrauterine development in rats.
2002 Jan
Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170.
2002 Jan
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
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
Sequential morphological and permeability changes in the rete capillaries during hyperglycaemia.
2002 Jun 1
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
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
Probucol and liver efficiency during chemically-induced hepatocarcinogenesis.
2002 Mar-Apr
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
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

Patents

20010000179
20
JP2003026665A
1
JP2004523497A
73
JP2004534728A
70
JP2005530894A
3
JP4214112B2
1
JPH02215595A
1
JPH0252361A
1
JPH04210978A
1
JPH05112556A
1
JPH054296A
1
JPH08231808A
1
JPH10193775A
1
JPS5551086A
1
JPS56106246A
1
JPS57136572A
1
JPS58138776A
1

Sample Use Guides

In Vivo Use Guide
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 Fri Jun 25 20:58:38 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:38 UTC 2021
Record UNII
T3CHA1B51H
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
Structure of ANTIPYRINE SALICYLATE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2A6
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of DICHLORALPHENAZONE
SALT/SOLVATE -> PARENT
Structure of ANTIPYRINE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Structure of CHLORAL HYDRATE ANTIPYRINE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of 3-(HYDROXYMETHYL)ANTIPYRINE GLUCURONIDE
METABOLITE -> PARENT
MAJOR
URINE
Structure of 4-HYDROXYANTIPYRINE GLUCURONIDE
METABOLITE -> PARENT
MAJOR
URINE
Structure of 4-HYDROXYANTIPYRINE
METABOLITE -> PARENT
Structure of 3-HYDROXYMETHYLANTIPYRINE
METABOLITE -> PARENT
MAJOR
URINE
Structure of EDARAVONE GLUCURONIDE
METABOLITE -> PARENT
MAJOR
URINE
Structure of 4-HYDROXYANTIPYRINE SULFATE
METABOLITE -> PARENT
MAJOR
URINE
Related Record Type Details
Structure of ANTIPYRINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966