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Substance Name: Isocarboxazid [USP:INN:BAN]
RN: 59-63-2
UNII: 34237V843T
InChIKey: XKFPYPQQHFEXRZ-UHFFFAOYSA-N

Note

  • An MAO inhibitor that is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in the treatment of panic disorder and the phobic disorders. (From AMA, Drug Evaluations Annual, 1994, p311).

Molecular Formula

  • C12-H13-N3-O2

Molecular Weight

  • 231.2537
 

Classification Codes

  • Antidepressant
  • Antidepressive Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Monoamine Oxidase Inhibitors
  • Mutation Data
  • Psychotropic Drugs
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Isocarboxazid
  • Isocarboxazid [USP:INN:BAN]

MeSH Heading

  • Isocarboxazid

Synonyms

  • 1-Benzyl-2-(5-methyl-3-isoxazolyl-carbonyl)hydrazine
  • 4-27-00-03999 (Beilstein Handbook Reference)
  • 5-Methyl-3-isoxazolecarboxylic acid 2-benzylhydrazide
  • Benazide
  • BRN 0201295
  • CCRIS 9178
  • EINECS 200-438-4
  • Enerzer
  • Isocarbonazid
  • Isocarbossazide
  • Isocarbossazide [DCIT]
  • Isocarboxazid
  • Isocarboxazida
  • Isocarboxazida [INN-Spanish]
  • Isocarboxazide
  • Isocarboxazide [INN-French]
  • Isocarboxazidum
  • Isocarboxazidum [INN-Latin]
  • Marplan
  • N'-Benzyl N-methyl-5-isoxazolecarboxylhydrazide-3
  • NSC 169893
  • Ro 5-0831
  • Ro 5-0831/1
  • UNII-34237V843T

Systematic Names

  • 3-Isoxazolecarboxylic acid, 5-methyl-, 2-(phenylmethyl)hydrazide
  • 3-Isoxazolecarboxylic acid, 5-methyl-, 2-benzylhydrazide
  • Isocarboxazid

Registry Numbers

CAS Registry Number

  • 59-63-2

FDA UNII

  • 34237V843T

System Generated Number

  • 0000059632

Structure Descriptors

InChI

InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)

InChIKey

XKFPYPQQHFEXRZ-UHFFFAOYSA-N

Smiles

Cc1onc(c1)C(=O)NNCc2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 40mg/kg (40mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Annals of the New York Academy of Sciences. Vol. 80, Pg. 626, 1959.
monkey LD50 oral 160mg/kg (160mg/kg)   Annals of the New York Academy of Sciences. Vol. 80, Pg. 626, 1959.
mouse LD50 intraperitoneal 138mg/kg (138mg/kg)   Journal of Medicinal and Pharmaceutical Chemistry. Vol. 2, Pg. 133, 1960.
mouse LD50 oral 193mg/kg (193mg/kg)   Annals of the New York Academy of Sciences. Vol. 80, Pg. 626, 1959.
mouse LD50 subcutaneous 150mg/kg (150mg/kg)   Toxicology and Applied Pharmacology. Vol. 39, Pg. 141, 1977.
rat LD50 intraperitoneal 199mg/kg (199mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 240, 1972.
rat LD50 oral 280mg/kg (280mg/kg)   Annals of the New York Academy of Sciences. Vol. 80, Pg. 626, 1959.
women TDLo oral 4800ug/kg/21W (4.8mg/kg)   Journal of Clinical Pyschopharmacology. Vol. 3, Pg. 42, 1983.
women TDLo oral 4800ug/kg/21W (4.8mg/kg)   Journal of Clinical Pyschopharmacology. Vol. 3, Pg. 42, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 105-106 deg C   EXP
pKa Dissociation Constant 10.4 (none)   EXP
log P (octanol-water) 1.49 (none)   EXP
Water Solubility 1600 mg/L 25 EST
Vapor Pressure 1.63E-07 mm Hg 25 EST
Henry's Law Constant 1.90E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.22E-11 cm3/molecule-sec 25 EST

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