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-1 131 Target ID: CHEMBL221 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8504
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Otitis media 42 Sources: http://www.otipax.com/index.php/en/otipax/what-is-otipax https://www.ncbi.nlm.nih.gov/pubmed/8239401	Palliative	Approved 8583	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 244 Sources: https://clinicaltrials.gov/ct2/show/NCT02153541 https://www.ncbi.nlm.nih.gov/pubmed/13906947	Palliative	Phase II 1147	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6818169 https://www.sdrugs.com/?c=drug&s=anodynine	Primary	Not Provided 511	Antipyrine Approved Use Unknown

T_1/2

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

F_unbound

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
inhibitor 2252 substrate 1946	substrate 1193 inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP3 246 OATP1B3 961 CYP2A6 879 MRP4 290 OATP1B1 1079 CYP2C19 2057 BSEP 550 CYP1A2 2153 CYP2E1 1060 OCT1 620 MRP2 499 CYP2J2 33 CYP19A1 429	CYP2B6 776 CYP2C8 810 CYP2E1 729 CYP2C18 149 CYP1A2 1197

Drug as perpetrator

Target	Modality	Activity
CYP2J2 36	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2206#section=Biological-Test-Results	inconclusive [IC50 50 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NDc0In19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NDc0In19	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >1000 uM]
MRP2 625	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1OTE4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >133 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2206#section=Biological-Test-Results Page: 421.0	no
OCT1 656	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1Njg1IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	weak [Inhibition 100 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/ \| https://pubmed.ncbi.nlm.nih.gov/9890159/	major
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/ \| https://pubmed.ncbi.nlm.nih.gov/9890159/	major
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/ \| https://pubmed.ncbi.nlm.nih.gov/9890159/	major
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	yes
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	yes
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	yes

PubMed

Title	Date	PubMed
[Insidious drug eruption].	2001	12116489
[Changes in the immune status parameters and their correction in various forms of tick-borne encephalitis].	2001	11697240
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
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
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
The effects of uterine and umbilical blood flows on the transfer of propofol across the human placenta during in vitro perfusion.	2001 Jul	11429356
Simultaneous measurement of cerebral blood flow and mRNA signals: pixel-based inter-modality correlational analysis.	2001 Jul 30	11478975
Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines.	2001 Jun	11525844
Metabolic functions of the liver during chemotherapy in children with acute lymphoblastic leukemia.	2001 Jun	11430632
Capillary electrophoretic analysis of carbohydrates derivatized by in-capillary condensation with 1-phenyl-3-methyl-5-pyrazolone.	2001 Mar 16	11293587
Metabolic capacity and interindividual variation in toxicokinetics of styrene in volunteers.	2001 May	11476153
Investigation of different combinations of derivatization, separation methods and electrospray ionization mass spectrometry for standard oligosaccharides and glycans from ovalbumin.	2001 May	11391813
Effects of 4-hydroxyantipyrine and its 4-O-sulfate on antipyrine as biodistribution promoter.	2001 May	11379775
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
Synthesis and antimicrobial activity of novel pyrazole, pyrazoline, pyrazolinone and pyrazolidinedione derivatives of benzimidazole.	2001 May-Jun	11486603
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
Placental transfer of SR49059 in the human dually perfused cotyledon in vitro.	2001 Nov	11718575
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
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
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
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
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
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
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
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
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

PHENAZONE

Preferred 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

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