U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C11H12N2O.C8H8O3
Molecular Weight 340.3731
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANTIPYRINE MANDELATE

SMILES

OC(C(O)=O)C1=CC=CC=C1.CN2N(C(=O)C=C2C)C3=CC=CC=C3

InChI

InChIKey=ICBPURKUPVLVCM-UHFFFAOYSA-N
InChI=1S/C11H12N2O.C8H8O3/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10;9-7(8(10)11)6-4-2-1-3-5-6/h3-8H,1-2H3;1-5,7,9H,(H,10,11)

HIDE SMILES / InChI

Molecular Formula C8H8O3
Molecular Weight 152.1473
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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.

Originator

Sources: DOI: 10.1016/S1366-0071(97)80033-2

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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.
Palliative
Unknown

Approved Use

Unknown
Primary
Antipyrine

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.7 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
0.97%
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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]
no
weak [Inhibition 100 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
An implantable bolus infusion pump for use in freely moving, nontethered rats.
2002-10
Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs, and monkeys.
2002-10
Myocardial protection of MCI-186 in rabbit ischemia-reperfusion.
2002-09-27
Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats.
2002-09-13
Direct analysis of nine pharmaceuticals in culture media by use of cartridge separation with electrospray mass spectrometric detection.
2002-09
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.
2002-08-23
The concordance of early antipyrine and thiopental distribution kinetics.
2002-08
Prediction of hepatic clearance and availability by cryopreserved human hepatocytes: an application of serum incubation method.
2002-08
4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamidinium acetate acetone hemisolvate.
2002-07
Effect of mild hypothermia on energy state recovery following transient forebrain ischemia in the gerbil.
2002-07
Estimation of intradermal disposition kinetics of drugs: II. Factors determining penetration of drugs from viable skin to muscular layer.
2002-06-04
Sequential morphological and permeability changes in the rete capillaries during hyperglycaemia.
2002-06-01
A study of immunoglobulin G glycosylation in monoclonal and polyclonal species by electrospray and matrix-assisted laser desorption/ionization mass spectrometry.
2002-06-01
Probucol and liver efficiency during chemically-induced hepatocarcinogenesis.
2002-05-17
Combined argatroban and edaravone caused additive neuroprotection against 15 min of forebrain ischemia in gerbils.
2002-05
[Pharmacological and clinical profile of the free radical scavenger edaravone as a neuroprotective agent].
2002-05
Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro.
2002-05
Next generation of everyday analgesics.
2002-04-10
Synthesis of syn and anti isomers of trans-cyclopropyl arginine.
2002-04-05
Migraine, Midrin, and Imitrex.
2002-04
Enzyme and plasma protein induction by multiple oral administrations of phenobarbital at a therapeutic dosage regimen in dogs.
2002-04
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans.
2002-04
Acute hypoxia and cytochrome P450-mediated hepatic drug metabolism in humans.
2002-04
The effect of amiloride on the in vivo effective permeability of amoxicillin in human jejunum: experience from a regional perfusion technique.
2002-04
Evaluation of the anti-vascular effects of combretastatin in rodent tumours by dynamic contrast enhanced MRI.
2002-04
Auto-protective redox buffering systems in stimulated macrophages.
2002-03-12
[Optimal conditions for extraction of "caffetin" and "saridon" tablet components from aqueous solutions].
2002-03-02
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.
2002-03
Influence of albumin supplementation on tacrolimus and cyclosporine therapy early after liver transplantation.
2002-03
Effect of growth hormone on hepatic cytochrome P450 activity in healthy elderly men.
2002-03
Exercise-induced oxidative stress in older adults as a function of habitual activity level.
2002-02
Albendazole metabolism in patients with neurocysticercosis: antipyrine as a multifunctional marker drug of cytochrome P450.
2002-02
Induction of hepatic and presystemic metabolism of antipyrine in the mice: rifampicin versus rifabutin.
2002-01-26
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes.
2002-01-12
Rational determination of transfer free energies of small drugs across the water-oil interface.
2002-01-03
Effects of prenatal exposure to combination of acetaminophen, isopropylantipyrine and caffeine on intrauterine development in rats.
2002-01
Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170.
2002-01
Transplacental transfer and metabolism of buprenorphine.
2002-01
Automated structural assignment of derivatized complex N-linked oligosaccharides from tandem mass spectra.
2002
Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration.
2002
[Absorption function of the large intestine in patients with nonspecific ulcerative colitis].
2002
A new method for measuring oxidative stress in claudicants during strenuous exercise using free radical derivatives of antipyrine as indicators: a pilot study.
2002
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
A female with asymptomatic primary biliary cirrhosis associated with pernicious anemia.
2001-12
Determination of ototoxicity of common otic drops using isolated cochlear outer hair cells.
2001-12
Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter.
2001-12
Combined effects of acetaminophen, isopropylantipyrine and caffeine on pregnant and nonpregnant liver.
2001-11
Schedule of controlled substances: placement of dichloralphenazone into Schedule IV. Final rule.
2001-08-16
[Insidious drug eruption].
2001
The radiological diagnosis of analgesic nephropathy.
1975-07
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:06:57 GMT 2025
Edited
by admin
on Mon Mar 31 22:06:57 GMT 2025
Record UNII
755160V3M8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTIPYRINE MANDELATE
MI  
Common Name English
TUSSEL
Preferred Name English
TUSSOL
Brand Name English
ANTIPYRINE, MANDELATE (1:1)
Common Name English
ANTIPYRINE MANDELATE, (±)-
Common Name English
ANTIPYRINE MANDELATE [MI]
Common Name English
ANTIPYRINE AMYGDALATE
Common Name English
BENZENEACETIC ACID, .ALPHA.-HYDROXY-, COMPD. WITH 1,2-DIHYDRO-1,5-DIMETHYL-2-PHENYL-3H-PYRAZOL-3-ONE (1:1)
Systematic Name English
ANTIPYRIN MANDELATE
Common Name English
Code System Code Type Description
FDA UNII
755160V3M8
Created by admin on Mon Mar 31 22:06:57 GMT 2025 , Edited by admin on Mon Mar 31 22:06:57 GMT 2025
PRIMARY
EPA CompTox
DTXSID00975709
Created by admin on Mon Mar 31 22:06:57 GMT 2025 , Edited by admin on Mon Mar 31 22:06:57 GMT 2025
PRIMARY
MERCK INDEX
m1973
Created by admin on Mon Mar 31 22:06:57 GMT 2025 , Edited by admin on Mon Mar 31 22:06:57 GMT 2025
PRIMARY Merck Index
CAS
603-64-5
Created by admin on Mon Mar 31 22:06:57 GMT 2025 , Edited by admin on Mon Mar 31 22:06:57 GMT 2025
PRIMARY
PUBCHEM
20056735
Created by admin on Mon Mar 31 22:06:57 GMT 2025 , Edited by admin on Mon Mar 31 22:06:57 GMT 2025
PRIMARY