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

• ChemBase编号: 1116
• 分子式: C12H13N3O2
• 平均质量: 231.25052
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide
• IUPAC传统名: isocarboxazid
• 商标名: BMIH; Benazide; Enerzer; Maraplan; Marplan; Marplon
• 别名: 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

登记号

• CAS号: 59-63-2
• PubChem SID: 46505330; 160964579
• PubChem CID: 3759
• ATC码: N06AF01
• CHEMBL: 1201168
• Chemspider ID: 3628
• DrugBank ID: DB01247
• KEGG ID: D02580
• 美国药典/FDA物质标识码: 34237V843T
• 维基百科标题: Isocarboxazid
• Medline Plus: a605036

理论计算性质

JChem

• Acid pKa: 12.021473
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.423697
• LogD (pH = 7.4): 1.4254845
• Log P: 1.4255166
• 摩尔折射率: 74.7803 cm^3
• 极化性: 23.79468 Å^3
• 极化表面积: 67.16 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.19
• LOG S: -3.01
• 溶解度: 2.24e-01 g/l

分子性质

理化性质

• 溶解度: 1.6 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; Chloroform; Methanol
• 外观: Pale Yellow Solid
• 熔点: 98-100°C
• 疏水性(logP): 2.4

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 给药途径: Oral
• 排泄: Urine
• 代谢: Liver
• 法定药品分级: Rx-only
• 妊娠期药物分类: C (USA)

详细说明

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.

参考文献

• 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)