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
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
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 |
---|---|---|---|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164816/ |
18 mg/kg single, oral dose: 18 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ANTIPYRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164824/ |
1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered: |
ANTIPYRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.97% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164816/ |
18 mg/kg single, oral dose: 18 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ANTIPYRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator​
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 50 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >1000 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
Page: 421.0 |
no | |||
weak [Inhibition 100 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
major | ||||
major | ||||
no | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
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[Insidious drug eruption]. | 2001 |
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[Changes in the immune status parameters and their correction in various forms of tick-borne encephalitis]. | 2001 |
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Clinical pharmacokinetics of quetiapine: an atypical antipsychotic. | 2001 |
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Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine. | 2001 Apr |
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Lack of hypercapnic increase in cerebral blood flow at high blood viscosity in conscious blood-exchanged rats. | 2001 Aug |
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An autoradiographic study of regional blood flow distribution in the rat kidney during ureteric obstruction--the role of vasoactive compounds. | 2001 Aug |
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Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter. | 2001 Dec |
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Exercise-induced oxidative stress in older adults as measured by antipyrine oxidation. | 2001 Dec |
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The effects of uterine and umbilical blood flows on the transfer of propofol across the human placenta during in vitro perfusion. | 2001 Jul |
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Simultaneous measurement of cerebral blood flow and mRNA signals: pixel-based inter-modality correlational analysis. | 2001 Jul 30 |
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Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines. | 2001 Jun |
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Metabolic functions of the liver during chemotherapy in children with acute lymphoblastic leukemia. | 2001 Jun |
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Capillary electrophoretic analysis of carbohydrates derivatized by in-capillary condensation with 1-phenyl-3-methyl-5-pyrazolone. | 2001 Mar 16 |
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Metabolic capacity and interindividual variation in toxicokinetics of styrene in volunteers. | 2001 May |
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Investigation of different combinations of derivatization, separation methods and electrospray ionization mass spectrometry for standard oligosaccharides and glycans from ovalbumin. | 2001 May |
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Effects of 4-hydroxyantipyrine and its 4-O-sulfate on antipyrine as biodistribution promoter. | 2001 May |
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Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process. | 2001 May |
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In vitro and in vivo evaluation of an oral system for time and/or site-specific drug delivery. | 2001 May 18 |
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Synthesis and antimicrobial activity of novel pyrazole, pyrazoline, pyrazolinone and pyrazolidinedione derivatives of benzimidazole. | 2001 May-Jun |
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Combined effects of acetaminophen, isopropylantipyrine and caffeine on pregnant and nonpregnant liver. | 2001 Nov |
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Antioxidant supplementation and exercise-induced oxidative stress in the 60-year-old as measured by antipyrine hydroxylates. | 2001 Nov |
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Placental transfer of SR49059 in the human dually perfused cotyledon in vitro. | 2001 Nov |
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Exercise training and oxidative stress in the elderly as measured by antipyrine hydroxylation products. | 2001 Oct |
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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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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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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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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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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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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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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.
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WHO-ATC |
S02DA03
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FDA ORPHAN DRUG |
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413
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PHENAZONE
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Antipyrine
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C76794
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ACTIVE MOIETY
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