N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide

• ChemBase ID: 1116
• Molecular Formular: C12H13N3O2
• Molecular Mass: 231.25052
• Monoisotopic Mass: 231.10077667
• SMILES: o1nc(C(=O)NNCc2ccccc2)cc1C
• Canonical SMILES: Cc1onc(c1)C(=O)NNCc1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide
• IUPAC Traditional name: isocarboxazid
• Brand Name: BMIH; Benazide; Enerzer; Maraplan; Marplan; Marplon
• Synonyms: Isocarboxazide [INN-French]; Isocarboxazide; Isocarboxazida [INN-Spanish]; Isocarboxazidum [INN-Latin]; Isocarboxyzid; Isocarbossazide [Dcit]; Isocarbonazid; Isocarboxazid; Marplan; 5-Methyl-3-isoxazole-carboxylic Acid 2-Benzylhydrazide; 3-(N-Benzylhydrazinocarbonyl)-5-methylisoxazole; Ro-5-0831

Database IDs

• CAS Number: 59-63-2
• PubChem SID: 46505330; 160964579
• PubChem CID: 3759
• ATC CODE: N06AF01
• CHEMBL: 1201168
• Chemspider ID: 3628
• DrugBank ID: DB01247
• KEGG ID: D02580
• Unique Ingredient Identifier: 34237V843T
• Wikipedia Title: Isocarboxazid
• Medline Plus: a605036

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.021473
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.423697
• LogD (pH = 7.4): 1.4254845
• Log P: 1.4255166
• Molar Refractivity: 74.7803 cm^3
• Polarizability: 23.79468 Å^3
• Polar Surface Area: 67.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.19
• LOG S: -3.01
• Solubility (Water): 2.24e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.6 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 98-100°C
• Hydrophobicity(logP): 2.4

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Urine
• Metabolism: Liver
• Legal Status: Rx-only
• Pregnancy Category: C (USA)

DETAILS

DrugBank - DB01247

• Drug Groups: approved
• Description: 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)
• Indication: May be used to treat major depressive disorder.
• Pharmacology: Isocarboxazid is a non-selective hydrazine monoamine oxidase (MAO) inhibitor used to treat depression. In vivo and in vitro studies demonstrated inhibition of MAO in the brain, heart, and liver. Depression is a complicated disease that is not fully understood. It is thought that depression may be linked to an imbalance of chemicals within the brain. When depression occurs, there may be a decrease in the amount of chemicals released from nerve cells in the brain. These chemicals are called monoamines. Monoamines are broken down by a chemical called monoamine oxidase. Isocarboxazid prevents monoamine oxidase from breaking down the monoamines. This results in an increased amount of active monoamines in the brain. By increasing the amount of monoamines in the brain, the imbalance of chemicals thought to be caused by depression is altered. This helps relieve the symptoms of depression.
• Toxicity: Signs of overdose include severe anxiety, confusion, convulsions, cool clammy skin, severe dizziness, severe drowsiness, fast and irregular pulse, fever, hallucinations, severe headache, high or low blood pressure, hyperactive reflexes, muscle stiffness, respiratory depression or failure, slowed reflexes, sweating, severe trouble in sleeping, and unusual irritability.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic and rapid (by oxidation).
• Absorption: Well absorbed from the gastrointestinal tract.
• References: Kennedy SH, Piran N, Warsh JJ, Prendergast P, Mainprize E, Whynot C, Garfinkel PE: A trial of isocarboxazid in the treatment of bulimia nervosa. J Clin Psychopharmacol. 1988 Dec;8(6):391-6. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - I789300

Monoamine oxidase inhibitor. Antidepressant.

REFERENCES

• Kennedy SH, Piran N, Warsh JJ, Prendergast P, Mainprize E, Whynot C, Garfinkel PE: A trial of isocarboxazid in the treatment of bulimia nervosa. J Clin Psychopharmacol. 1988 Dec;8(6):391-6. Pubmed
• Rudy, B.C., et al.: Anal. Profiles Drug Subs., 2, 295 (1973)