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
Molecular Formula | C11H12N2O |
Molecular Weight | 188.2258 |
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 |
---|---|---|---|
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 |
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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 |
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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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Dissociation of brain edema induced by cold injury in rat model: MR imaging and perfusion studies with 14C-iodo-antipyrine. | 2001 Aug |
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Impairment of metabolic function in chronic hepatitis C is related to factors associated with resistance to therapy. | 2001 Aug |
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Exercise-induced oxidative stress in older adults as measured by antipyrine oxidation. | 2001 Dec |
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Derivative ratio spectra-zero crossing spectrophotometry and LC method applied to the quantitative determination of paracetamol, propyphenazone and caffeine in ternary mixtures. | 2001 Dec |
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The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides. | 2001 Feb |
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Efficacy of naturopathic extracts in the management of ear pain associated with acute otitis media. | 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 of some triazolyl-antipyrine derivatives and investigation of analgesic activity. | 2001 Jul-Aug |
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[Effect of hypoxic stress on xenobiotic metabolism and activities of various isoforms of cytochrome P-450]. | 2001 Jul-Aug |
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Metabolic functions of the liver during chemotherapy in children with acute lymphoblastic leukemia. | 2001 Jun |
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Direct nuclear magnetic resonance spectroscopic analysis of (13)C-labeled antipyrine metabolites in human urine. | 2001 Jun |
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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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Antioxidant supplementation and exercise-induced oxidative stress in the 60-year-old as measured by antipyrine hydroxylates. | 2001 Nov |
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Phosphorylation of cyclic adenosine monophosphate response element binding protein in oligodendrocytes in the corpus callosum after focal cerebral ischemia in the rat. | 2001 Oct |
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Regioselective synthesis of polysubstituted pyrazoles and isoxazoles. | 2001 Oct 5 |
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Ten-year combination treatment with colchicine and ursodeoxycholic acid for primary biliary cirrhosis: a double-blind, placebo-controlled trial on symptomatic patients. | 2001 Sep |
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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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Synthesis of syn and anti isomers of trans-cyclopropyl arginine. | 2002 Apr 5 |
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Determination of oligosaccharides in Pompe disease by electrospray ionization tandem mass spectrometry. | 2002 Jan |
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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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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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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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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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Record UNII |
T3CHA1B51H
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Record Status |
Validated (UNII)
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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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QN02BB71
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WHO-ATC |
N02BB51
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31225
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m1973
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DTXSID6021117
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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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60-80-0
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T3CHA1B51H
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1040005
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CHEMBL277474
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413
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PHENAZONE
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Antipyrine
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C76794
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SUB09753MIG
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100000085208
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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 | |||
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METABOLITE -> PARENT |
MAJOR
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |