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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

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
Antioxidants reduce oxidative stress in claudicants.
2001 Apr
Dissociation of brain edema induced by cold injury in rat model: MR imaging and perfusion studies with 14C-iodo-antipyrine.
2001 Aug
Exercise-induced oxidative stress in older adults as measured by antipyrine oxidation.
2001 Dec
Transplacental transfer of amitriptyline and nortriptyline in isolated perfused human placenta.
2001 Feb
Pesticidal properties of parthenin (from Parthenium hysterophorus) and related compounds.
2001 Jan
Efficacy of naturopathic extracts in the management of ear pain associated with acute otitis media.
2001 Jul
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
Quantitative analysis of rat inner ear blood flow using the iodo[(14)C]antipyrine technique.
2001 Mar
Analysis of sialo-N-glycans in glycoproteins as 1-phenyl-3-methyl-5-pyrazolone derivatives by capillary electrophoresis.
2001 Mar 2
[The liver monooxygenase system activity in the long-term compression syndrome and treatment with benzonal in prepubertal rats and rabbits].
2001 Mar-Apr
Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective.
2001 Nov-Dec
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 effect of amiloride on the in vivo effective permeability of amoxicillin in human jejunum: experience from a regional perfusion technique.
2002 Apr
The concordance of early antipyrine and thiopental distribution kinetics.
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
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
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
Combined argatroban and edaravone caused additive neuroprotection against 15 min of forebrain ischemia in gerbils.
2002 May
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
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 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
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BASIS OF STRENGTH->SUBSTANCE
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