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-1 125 Target ID: CHEMBL221 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8146
Cyclooxygenase-2 191 Target ID: CHEMBL230 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8146

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 8307	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 234 Sources: https://clinicaltrials.gov/ct2/show/NCT02153541 https://www.ncbi.nlm.nih.gov/pubmed/13906947	Palliative	Phase II 1133	Unknown Approved Use Unknown
Pain 607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6818169 https://www.sdrugs.com/?c=drug&s=anodynine	Primary	Not Provided 505	Antipyrine Approved Use Unknown

PubMed

Title	Date	PubMed
The radiological diagnosis of analgesic nephropathy.	1975 Jul	1201638
[Insidious drug eruption].	2001	12116489
[Changes in the immune status parameters and their correction in various forms of tick-borne encephalitis].	2001	11697240
Schedule of controlled substances: placement of dichloralphenazone into Schedule IV. Final rule.	2001 Aug 16	11794309
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
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes.	2001 Jan-Feb	11785906
Combined effects of acetaminophen, isopropylantipyrine and caffeine on pregnant and nonpregnant liver.	2001 Nov	11926611
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
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
[Absorption function of the large intestine in patients with nonspecific ulcerative colitis].	2002	12046397
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	11999141
Migraine, Midrin, and Imitrex.	2002 Apr	12010397
Enzyme and plasma protein induction by multiple oral administrations of phenobarbital at a therapeutic dosage regimen in dogs.	2002 Apr	12000532
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans.	2002 Apr	11999127
Acute hypoxia and cytochrome P450-mediated hepatic drug metabolism in humans.	2002 Apr	11956503
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
The concordance of early antipyrine and thiopental distribution kinetics.	2002 Aug	12130720
Prediction of hepatic clearance and availability by cryopreserved human hepatocytes: an application of serum incubation method.	2002 Aug	12124306
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
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
4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamidinium acetate acetone hemisolvate.	2002 Jul	12094065
Effect of mild hypothermia on energy state recovery following transient forebrain ischemia in the gerbil.	2002 Jul	12070748
Sequential morphological and permeability changes in the rete capillaries during hyperglycaemia.	2002 Jun 1	12112446
A study of immunoglobulin G glycosylation in monoclonal and polyclonal species by electrospray and matrix-assisted laser desorption/ionization mass spectrometry.	2002 Jun 1	12018942
Estimation of intradermal disposition kinetics of drugs: II. Factors determining penetration of drugs from viable skin to muscular layer.	2002 Jun 4	12052698
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
Auto-protective redox buffering systems in stimulated macrophages.	2002 Mar 12	11914132
Probucol and liver efficiency during chemically-induced hepatocarcinogenesis.	2002 Mar-Apr	12014681
Combined argatroban and edaravone caused additive neuroprotection against 15 min of forebrain ischemia in gerbils.	2002 May	12074843
[Pharmacological and clinical profile of the free radical scavenger edaravone as a neuroprotective agent].	2002 May	12061142
Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro.	2002 May	12038785
Next generation of everyday analgesics.	2002 May-Jun	11941381
An implantable bolus infusion pump for use in freely moving, nontethered rats.	2002 Oct	12234827
Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs, and monkeys.	2002 Oct	12228180
Direct analysis of nine pharmaceuticals in culture media by use of cartridge separation with electrospray mass spectrometric detection.	2002 Sep	12207243
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
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