4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide

• ChemBase编号: 1042
• 分子式: C13H17ClN2O2
• 平均质量: 268.73928
• 单一同位素质量: 268.09785547
• SMILES: Clc1ccc(C(=O)NCCN2CCOCC2)cc1
• Canonical SMILES: O=C(c1ccc(cc1)Cl)NCCN1CCOCC1
• InChI: InChI=1S/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)
• InChIKey: YHXISWVBGDMDLQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide
• IUPAC传统名: moclobemide; arima
• 商标名: Aurorix; Manerix
• 别名: Moclobemida [INN-Spanish]; Moclobemide [Usan:Ban:Inn]; Moclobemidum [INN-Latin]; 4-Chlor-N-(2-morpholinoethyl)benzamid; 4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide; 4-Chloro-N-(2-morpholin-4-yl-ethyl)-benzamide; Moclamine; Moclamide; Moclobemid; Moclaime; p-Chloro-N-(2-morpholinoethyl)benzamide; moclobemide; Moclobemide; 4-chloro-N-[2-(4-morpholinyl)ethyl]benzamide; Aurorix; Moclobemide; Ro-11-1163, Aurorix, Manerix, Moclamine, p-Chloro-N-(2-morpholinoethyl)benzamide

登记号

• CAS号: 71320-77-9
• MDL号: MFCD00865388
• PubChem SID: 46504667; 160964505
• PubChem CID: 4235
• ATC码: N06AG02
• CHEMBL: 86304
• Chemspider ID: 4087
• DrugBank ID: DB01171
• KEGG ID: D02561
• 美国药典/FDA物质标识码: PJ0Y7AZB63
• 维基百科标题: Moclobemide

理论计算性质

JChem

• Acid pKa: 14.732517
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.8195106
• LogD (pH = 7.4): 1.4341191
• Log P: 1.4517509
• 摩尔折射率: 71.9315 cm^3
• 极化性: 27.590597 Å^3
• 极化表面积: 41.57 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: 1.56
• LOG S: -2.38
• 溶解度: 1.12e+00 g/l

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL; Isopropanol; Methanol
• 外观: white solid; White to Off-White Solid
• 熔点: 135-137°C
• 疏水性(logP): 1.5

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: CV2462000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 22-37/38-41
• 安全公开号: 26-39
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• GHS危险声明: H302-H315-H318-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: room temp

药理学性质

• 作用靶点: MAO
• 给药途径: oral
• 生物利用度: 60% after first dose, >80% after first week of treatment
• 排泄: renally/in urine
• 半衰期: 1 to 2 hours
• 代谢: Liver
• 法定药品分级: Rx-only; not a controlled substance
• 妊娠期药物分类: B3 (Australia)

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C13H17ClN2O2

详细说明

DrugBank - DB01171

• Drug Groups: approved
• Description: A reversible monoamine oxidase inhibitor (MAOI) selective for isoform A (RIMA) used to treat major depressive disorder.
• Indication: For the treatment of depression.
• Pharmacology: Moclobemide belongs to a class of MAOI antidepressants known as reversible inhibitors of monoamine oxidase type-A (RIMAs). The primary role of monoamine oxidase MAO lies in the metabolism of and regulation of the levels of monoamines (serotonin, norepinephrine, and dopamine). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Since depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms. RIMAs demonstrate transient inhibition of the substrate binding site of MAO-A as well as competitive displacement from this site by bioamines. The RIMAs are distinguished from the older monoamine oxidase inhibitors (MAOIs) by their selectivity and reversibility.
• Toxicity: LD50 (mouse) is 730mg/kg and LD50 (rat) is 1,300mg/kg. Signs of toxicity include hypertension, drowsiness, dizziness, confusion, tremors, headache, agitation, muscle rigidity and seizures.
• Affected Organisms: Humans and other mammals
• Biotransformation: Moclobemide is almost completely metabolized in the liver by Cytochrome P450 2C19 and 2D6.
• Absorption: Well absorbed from the gastrointestinal tract (> 95%). The presence of food reduces the rate but not the extent of absorption. Hepatic first pass metabolism reduces bioavailability to 45-70% following administration of a single dose, but increases to 80% with multiple dosing as a result of saturation of the first pass effect. Peak plasma concentrations are reached within 1 - 2 hours following oral administration.
• Half Life: 1-2 hours (4 hours in cirrhotic patients); metabolites are renally excreted
• Protein Binding: Approximately 50% (primarily to albumin)
• External Links: Wikipedia

Sigma Aldrich - M3071

Biochem/physiol Actions
Moclobemide is a reversible monoamine oxidase A inhibitor (MAOI); antidepressant. Elimination half-life in humans = 1 -3 hrs; absolute oral bioavailability. Unlike other MAO inhibitors, does not significantly increase blood pressure in humans upon combination with tyramine.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M3071.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M481000

A reversible monoamine oxidase inhibitor.

参考文献

• Wiesel, F.A., et al.: Eur. J. Clin. Pharmacol., 28, 89 (1985)
• Burkard, W.P., et al.: J. Pharmacol. Exp. Ther., 248, 391 (1989)