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Substance Name: Antipyrine [USP:JAN]
RN: 60-80-0
UNII: T3CHA1B51H
InChIKey: VEQOALNAAJBPNY-UHFFFAOYSA-N

Note

  • An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

Molecular Formula

  • C11-H12-N2-O

Molecular Weight

  • 188.2288
 

Classification Codes

  • Agricultural Chemical
  • Analgesic
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Fungicide, Bactericide, Wood Preservative
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Sensory System Agents
  • Tumor Data

Names and Synonyms

Name of Substance

  • Antipyrine
  • Antipyrine [USP:JAN]
  • Phenazone [INN]

MeSH Heading

  • Antipyrine

Synonyms

  • 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
  • 1-Phenyl-2,3-dimethyl-5-pyrazolone
  • 1-Phenyl-2,3-dimethylpyrazole-5-one
  • 2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one
  • 2,3-Dimethyl-1-phenyl-5-pyrazolone
  • 3-Antipyrine
  • AI3-15293
  • Analgesine
  • Anodynin
  • Anodynine
  • Antipirin
  • Antipyrin
  • Antipyrine
  • Antipyrinum
  • Apirelina
  • Azophen
  • Azophene
  • Azophenum
  • CCRIS 1369
  • Dimethyloxychinizin
  • Dimethyloxyquinazine
  • EC 200-486-6
  • EINECS 200-486-6
  • Fenazon
  • Fenazon [Czech]
  • Fenazona
  • Fenazona [INN-Spanish]
  • Fenazone
  • Methozin
  • NSC 7945
  • Oxydimethylquinazine
  • Parodyne
  • Phenazon
  • Phenazone
  • Phenazone (pharmaceutical)
  • Phenazonum
  • Phenazonum [INN-Latin]
  • Phenozone
  • Phenylon
  • Phenylone
  • Pyrazophyl
  • Sedatin
  • Sedatine
  • UNII-T3CHA1B51H

Systematic Names

  • 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
  • 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-
  • Antipyrine
  • Phenazone

Mixture Name

  • Auralgan

Registry Numbers

CAS Registry Number

  • 60-80-0

FDA UNII

  • T3CHA1B51H

Other Registry Numbers

  • 123175-91-7
  • 5779-41-9

System Generated Number

  • 0000060800

Structure Descriptors

InChI

1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3

InChIKey

VEQOALNAAJBPNY-UHFFFAOYSA-N

Smiles

Cc1cc(=O)n(n1C)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 525mg/kg (525mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 39, Pg. 177, 1930.
cat LDLo oral 1250mg/kg (1250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 39, Pg. 177, 1930.
cat LDLo rectal 800mg/kg (800mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 33, Pg. 10, 1944.
cat LDLo subcutaneous 700mg/kg (700mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
dog LDLo oral 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
frog LDLo subcutaneous 2gm/kg (2000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
guinea pig LDLo oral 1400mg/kg (1400mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 14, 1959.
guinea pig LDLo subcutaneous 1600mg/kg (1600mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: PULSE RATE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 186, Pg. 195, 1937.
man LDLo unreported 74mg/kg (74mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 750mg/kg (750mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 686, 1960.
mouse LD50 oral 1310mg/kg (1310mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 137, 1956.
mouse LD50 subcutaneous 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 214, 1967.
rabbit LDLo intravenous 600mg/kg (600mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 14, 1959.
rabbit LDLo subcutaneous 1gm/kg (1000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
rat LD50 oral 1705mg/kg (1705mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 401, 1959.
rat LDLo subcutaneous 1570mg/kg (1570mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 186, Pg. 195, 1937.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 114 deg C   EXP
Boiling Point 319 deg C   EXP
pKa Dissociation Constant 1.4 (none)   EXP
log P (octanol-water) 0.38 (none)   EXP
Water Solubility 5.19E+04 mg/L 25 EXP
Vapor Pressure 3.06E-05 mm Hg 25 EST
Henry's Law Constant 6.65E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.21E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.