ANTIPYRINE

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 Search

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
Sources: DOI: 10.1016/S1366-0071(97)80033-2 | Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ | https://mri.cts-mrp.eu/download/LV_H_0127_001_FinalSPC.pdf | Leonard, B.J. (1977) Toxicological Aspects of Food Safety, page 132, retrieved from: https://books.google.ru/books?id=563tCAAAQBAJ | https://www.sdrugs.com/?c=drug&s=anodynine

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 124 Target ID: CHEMBL221 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 7728
Cyclooxygenase-2 189 Target ID: CHEMBL230 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 7728

Conditions

Condition	Modality	Highest Phase	Product
Otitis media 39 Sources: http://www.otipax.com/index.php/en/otipax/what-is-otipax https://www.ncbi.nlm.nih.gov/pubmed/8239401	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.
Asthma 227 Sources: https://clinicaltrials.gov/ct2/show/NCT02153541 https://www.ncbi.nlm.nih.gov/pubmed/13906947	Palliative	Phase II 1101	Unknown Approved Use Unknown
Pain 580 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6818169 https://www.sdrugs.com/?c=drug&s=anodynine	Primary	Not Provided 492	Antipyrine Approved Use Unknown

PubMed

Title	Date	PubMed
Antioxidants reduce oxidative stress in claudicants.	2001 Apr	11266271
Dissociation of brain edema induced by cold injury in rat model: MR imaging and perfusion studies with 14C-iodo-antipyrine.	2001 Aug	11577758
Exercise-induced oxidative stress in older adults as measured by antipyrine oxidation.	2001 Dec	11735098
Transplacental transfer of amitriptyline and nortriptyline in isolated perfused human placenta.	2001 Feb	11243492
Pesticidal properties of parthenin (from Parthenium hysterophorus) and related compounds.	2001 Jan	11455638
Efficacy of naturopathic extracts in the management of ear pain associated with acute otitis media.	2001 Jul	11434846
Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines.	2001 Jun	11525844
Metabolic functions of the liver during chemotherapy in children with acute lymphoblastic leukemia.	2001 Jun	11430632
Quantitative analysis of rat inner ear blood flow using the iodo[(14)C]antipyrine technique.	2001 Mar	11223306
Analysis of sialo-N-glycans in glycoproteins as 1-phenyl-3-methyl-5-pyrazolone derivatives by capillary electrophoresis.	2001 Mar 2	11261727
[The liver monooxygenase system activity in the long-term compression syndrome and treatment with benzonal in prepubertal rats and rabbits].	2001 Mar-Apr	11548454
Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective.	2001 Nov-Dec	11695253
Exercise training and oxidative stress in the elderly as measured by antipyrine hydroxylation products.	2001 Oct	11697140
Automated structural assignment of derivatized complex N-linked oligosaccharides from tandem mass spectra.	2002	12207362
Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration.	2002	12097837
The effect of amiloride on the in vivo effective permeability of amoxicillin in human jejunum: experience from a regional perfusion technique.	2002 Apr	11923059
The concordance of early antipyrine and thiopental distribution kinetics.	2002 Aug	12130720
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	12161256
Determination of oligosaccharides in Pompe disease by electrospray ionization tandem mass spectrometry.	2002 Jan	11751548
Rational determination of transfer free energies of small drugs across the water-oil interface.	2002 Jan 3	11754587
4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamidinium acetate acetone hemisolvate.	2002 Jul	12094065
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	12071338
Influence of albumin supplementation on tacrolimus and cyclosporine therapy early after liver transplantation.	2002 Mar	11910567
Effect of growth hormone on hepatic cytochrome P450 activity in healthy elderly men.	2002 Mar	11907490
Combined argatroban and edaravone caused additive neuroprotection against 15 min of forebrain ischemia in gerbils.	2002 May	12074843
Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats.	2002 Sep 13	12231392
Myocardial protection of MCI-186 in rabbit ischemia-reperfusion.	2002 Sep 27	12215372

Patents

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

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

Common Name

English

ANTIPYRINE [USP]

Common Name

English

PHENAZONE [EP]

Common Name

English

ANTIPYRINUM [HPUS]

Common Name

English

PHENAZONE [INN]

Common Name

English

PHENAZONE

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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ANTIPYRINE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

USP

Amount:


					7A1009H34F

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4-HYDROXYANTIPYRINE GLUCURONIDE

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Related Record Type Details


					T3CHA1B51H

ANTIPYRINE

ACTIVE MOIETY

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides