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
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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL221 |
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Target ID: CHEMBL230 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Finoten Approved UseAntipyrine 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. |
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Palliative | Unknown Approved UseUnknown |
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Primary | Antipyrine Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The radiological diagnosis of analgesic nephropathy. | 1975 Jul |
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[Insidious drug eruption]. | 2001 |
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Schedule of controlled substances: placement of dichloralphenazone into Schedule IV. Final rule. | 2001 Aug 16 |
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A female with asymptomatic primary biliary cirrhosis associated with pernicious anemia. | 2001 Dec |
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Determination of ototoxicity of common otic drops using isolated cochlear outer hair cells. | 2001 Dec |
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Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter. | 2001 Dec |
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Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes. | 2001 Jan-Feb |
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Combined effects of acetaminophen, isopropylantipyrine and caffeine on pregnant and nonpregnant liver. | 2001 Nov |
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[Optimal conditions for extraction of "caffetin" and "saridon" tablet components from aqueous solutions]. | 2001 Nov-Dec |
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Induction of hepatic and presystemic metabolism of antipyrine in the mice: rifampicin versus rifabutin. | 2001 Oct-Dec |
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Automated structural assignment of derivatized complex N-linked oligosaccharides from tandem mass spectra. | 2002 |
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Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration. | 2002 |
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[Absorption function of the large intestine in patients with nonspecific ulcerative colitis]. | 2002 |
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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 |
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Migraine, Midrin, and Imitrex. | 2002 Apr |
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Enzyme and plasma protein induction by multiple oral administrations of phenobarbital at a therapeutic dosage regimen in dogs. | 2002 Apr |
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The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans. | 2002 Apr |
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Acute hypoxia and cytochrome P450-mediated hepatic drug metabolism in humans. | 2002 Apr |
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The effect of amiloride on the in vivo effective permeability of amoxicillin in human jejunum: experience from a regional perfusion technique. | 2002 Apr |
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Synthesis of syn and anti isomers of trans-cyclopropyl arginine. | 2002 Apr 5 |
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The concordance of early antipyrine and thiopental distribution kinetics. | 2002 Aug |
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Prediction of hepatic clearance and availability by cryopreserved human hepatocytes: an application of serum incubation method. | 2002 Aug |
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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 |
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Exercise-induced oxidative stress in older adults as a function of habitual activity level. | 2002 Feb |
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Albendazole metabolism in patients with neurocysticercosis: antipyrine as a multifunctional marker drug of cytochrome P450. | 2002 Feb |
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Effects of prenatal exposure to combination of acetaminophen, isopropylantipyrine and caffeine on intrauterine development in rats. | 2002 Jan |
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Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170. | 2002 Jan |
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Transplacental transfer and metabolism of buprenorphine. | 2002 Jan |
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Determination of oligosaccharides in Pompe disease by electrospray ionization tandem mass spectrometry. | 2002 Jan |
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Rational determination of transfer free energies of small drugs across the water-oil interface. | 2002 Jan 3 |
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4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamidinium acetate acetone hemisolvate. | 2002 Jul |
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Effect of mild hypothermia on energy state recovery following transient forebrain ischemia in the gerbil. | 2002 Jul |
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Sequential morphological and permeability changes in the rete capillaries during hyperglycaemia. | 2002 Jun 1 |
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A study of immunoglobulin G glycosylation in monoclonal and polyclonal species by electrospray and matrix-assisted laser desorption/ionization mass spectrometry. | 2002 Jun 1 |
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Estimation of intradermal disposition kinetics of drugs: II. Factors determining penetration of drugs from viable skin to muscular layer. | 2002 Jun 4 |
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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 |
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Influence of albumin supplementation on tacrolimus and cyclosporine therapy early after liver transplantation. | 2002 Mar |
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Effect of growth hormone on hepatic cytochrome P450 activity in healthy elderly men. | 2002 Mar |
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Auto-protective redox buffering systems in stimulated macrophages. | 2002 Mar 12 |
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Probucol and liver efficiency during chemically-induced hepatocarcinogenesis. | 2002 Mar-Apr |
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Combined argatroban and edaravone caused additive neuroprotection against 15 min of forebrain ischemia in gerbils. | 2002 May |
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[Pharmacological and clinical profile of the free radical scavenger edaravone as a neuroprotective agent]. | 2002 May |
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Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro. | 2002 May |
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Next generation of everyday analgesics. | 2002 May-Jun |
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An implantable bolus infusion pump for use in freely moving, nontethered rats. | 2002 Oct |
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Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs, and monkeys. | 2002 Oct |
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Direct analysis of nine pharmaceuticals in culture media by use of cartridge separation with electrospray mass spectrometric detection. | 2002 Sep |
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Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats. | 2002 Sep 13 |
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Myocardial protection of MCI-186 in rabbit ischemia-reperfusion. | 2002 Sep 27 |
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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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02037893
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7890260
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
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admin
on
Edited
Fri Jun 25 20:58:38 UTC 2021
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on
Fri Jun 25 20:58:38 UTC 2021
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Record UNII |
T3CHA1B51H
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
S02DA03
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NCI_THESAURUS |
C257
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WHO-ATC |
N02BB71
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WHO-VATC |
QS02DA03
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FDA ORPHAN DRUG |
5284
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WHO-VATC |
QN02BB01
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WHO-ATC |
N02BB01
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WHO-VATC |
QN02BB51
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WHO-VATC |
QN02BB71
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WHO-ATC |
N02BB51
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M1973
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60-80-0
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DB01435
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T3CHA1B51H
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D000983
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1001
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2206
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861
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CHEMBL277474
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413
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PHENAZONE
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Antipyrine
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1040005
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C76794
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SUB09753MIG
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200-486-6
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |