ANTIPYRINE

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 Search

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

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-1 127 Target ID: CHEMBL221 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8297
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Otitis media 41 Sources: http://www.otipax.com/index.php/en/otipax/what-is-otipax https://www.ncbi.nlm.nih.gov/pubmed/8239401	Palliative	Approved 8429	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 241 Sources: https://clinicaltrials.gov/ct2/show/NCT02153541 https://www.ncbi.nlm.nih.gov/pubmed/13906947	Palliative	Phase II 1132	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6818169 https://www.sdrugs.com/?c=drug&s=anodynine	Primary	Not Provided 504	Antipyrine Approved Use Unknown

PubMed

Title	Date	PubMed
The radiological diagnosis of analgesic nephropathy.	1975 Jul	1201638
[Insidious drug eruption].	2001	12116489
Clinical pharmacokinetics of quetiapine: an atypical antipsychotic.	2001	11510628
Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine.	2001 Apr	11318886
Antioxidants reduce oxidative stress in claudicants.	2001 Apr	11266271
Lack of hypercapnic increase in cerebral blood flow at high blood viscosity in conscious blood-exchanged rats.	2001 Aug	11506114
An autoradiographic study of regional blood flow distribution in the rat kidney during ureteric obstruction--the role of vasoactive compounds.	2001 Aug	11488744
Schedule of controlled substances: placement of dichloralphenazone into Schedule IV. Final rule.	2001 Aug 16	11794309
A female with asymptomatic primary biliary cirrhosis associated with pernicious anemia.	2001 Dec	11851845
Determination of ototoxicity of common otic drops using isolated cochlear outer hair cells.	2001 Dec	11802005
Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter.	2001 Dec	11767111
Exercise-induced oxidative stress in older adults as measured by antipyrine oxidation.	2001 Dec	11735098
Derivative ratio spectra-zero crossing spectrophotometry and LC method applied to the quantitative determination of paracetamol, propyphenazone and caffeine in ternary mixtures.	2001 Dec	11600288
Transplacental transfer of amitriptyline and nortriptyline in isolated perfused human placenta.	2001 Feb	11243492
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes.	2001 Jan-Feb	11785906
Simultaneous measurement of cerebral blood flow and mRNA signals: pixel-based inter-modality correlational analysis.	2001 Jul 30	11478975
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
Capillary electrophoretic analysis of carbohydrates derivatized by in-capillary condensation with 1-phenyl-3-methyl-5-pyrazolone.	2001 Mar 16	11293587
Analysis of sialo-N-glycans in glycoproteins as 1-phenyl-3-methyl-5-pyrazolone derivatives by capillary electrophoresis.	2001 Mar 2	11261727
Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process.	2001 May	11303070
In vitro and in vivo evaluation of an oral system for time and/or site-specific drug delivery.	2001 May 18	11337063
Antioxidant supplementation and exercise-induced oxidative stress in the 60-year-old as measured by antipyrine hydroxylates.	2001 Nov	11737955
Effects of recombinant tissue plasminogen activator after intraluminal thread occlusion in mice: role of hemodynamic alterations.	2001 Nov	11692029
Polymeric transdermal drug penetration enhancer. The enhancing effect of oligodimethylsiloxane containing a glucopyranosyl end group.	2001 Nov 9	11689259
[Optimal conditions for extraction of "caffetin" and "saridon" tablet components from aqueous solutions].	2001 Nov-Dec	11871327
Exercise training and oxidative stress in the elderly as measured by antipyrine hydroxylation products.	2001 Oct	11697140
Theoretical considerations on the in vivo intestinal permeability determination by means of the single pass and recirculating techniques.	2001 Oct 23	11604262
Induction of hepatic and presystemic metabolism of antipyrine in the mice: rifampicin versus rifabutin.	2001 Oct-Dec	11808861
Ten-year combination treatment with colchicine and ursodeoxycholic acid for primary biliary cirrhosis: a double-blind, placebo-controlled trial on symptomatic patients.	2001 Sep	11552915
The effect of amiloride on the in vivo effective permeability of amoxicillin in human jejunum: experience from a regional perfusion technique.	2002 Apr	11923059
Evaluation of the anti-vascular effects of combretastatin in rodent tumours by dynamic contrast enhanced MRI.	2002 Apr	11870904
Synthesis of syn and anti isomers of trans-cyclopropyl arginine.	2002 Apr 5	11925253
Exercise-induced oxidative stress in older adults as a function of habitual activity level.	2002 Feb	12028219
Albendazole metabolism in patients with neurocysticercosis: antipyrine as a multifunctional marker drug of cytochrome P450.	2002 Feb	11847531
Effects of prenatal exposure to combination of acetaminophen, isopropylantipyrine and caffeine on intrauterine development in rats.	2002 Jan	12046720
Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170.	2002 Jan	11801713
Transplacental transfer and metabolism of buprenorphine.	2002 Jan	11752093
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
Estimation of intradermal disposition kinetics of drugs: II. Factors determining penetration of drugs from viable skin to muscular layer.	2002 Jun 4	12052698
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
Auto-protective redox buffering systems in stimulated macrophages.	2002 Mar 12	11914132
Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs, and monkeys.	2002 Oct	12228180
Myocardial protection of MCI-186 in rabbit ischemia-reperfusion.	2002 Sep 27	12215372
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	12017201

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.

Name

Type

Language

ANTIPYRINE

Common 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

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

PHENAZONE

Official 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