methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate

• ChemBase编号: 525
• 分子式: C16H13N3O3
• 平均质量: 295.29272
• 单一同位素质量: 295.09569129
• SMILES: O=C(c1cc2[nH]c(nc2cc1)NC(=O)OC)c1ccccc1
• Canonical SMILES: COC(=O)Nc1nc2c([nH]1)cc(cc2)C(=O)c1ccccc1
• InChI: InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)
• InChIKey: OPXLLQIJSORQAM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate; methyl N-(5-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
• IUPAC传统名: telmin; mebendazole; methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate; vermox
• 商标名: Vermirax; Vermox; Vermox (TN); Verpanyl; Bantenol; Besantin; Equivurm Plus; Lomper; MBDZ; MEBENDAZOLE, 99%; Mebendazole (JAN/USP); Mebendazole(USAN); Mebenoazole; Mebenvet; Mebex; Mebutar; Noverme; Ovitelmin; Pantelmin; Telmin; Vermicidin
• 别名: 5-苯甲酰-2-苯并咪唑胺甲酸甲酯; N-(5-苯甲酰-1H-苯并咪唑-2-基)氨基甲酸甲酯; 甲苯咪唑; 甲苯达唑; Mebendazole; N-(6-Benzoyl-1H-benzimidazol-2-yl)carbamic Acid Methyl Ester; Bantenol; Besantin; Mebenvet; Mebex; Noverme; Ovitelmin; Pantelmin; R 17635; methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate; 5-benzoyl-2-benzimidazolylcarbamic acid methyl ester; Equivurm Plus; Lomper; MBDZ; Mebenoazole; Mebutar; Telmin; Vermicidin; Vermirax; Vermox; Verpanyl; Mebendazole; methyl (5-benzoyl-1H-benzo[d]imidazol-2-yl)carbamate; 5-Benzoyl-2-benzimidazolecarbamic acid methyl ester; Mebendazol; Methyl N-(5-benzoyl-1H-benzimidazol-2-yl)carbamate; methyl (5-benzoyl-1H-benzimidazol-2-yl)carbamate

登记号

• CAS号: 31431-39-7
• EC号: 250-635-4
• MDL号: MFCD00408814; MFCD00057872
• Beilstein号: 759809
• PubChem SID: 24870130; 24896742; 160963988; 46508807
• PubChem CID: 4030

理论计算性质

JChem

• Acid pKa: 9.168718
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.2565598
• LogD (pH = 7.4): 3.2536292
• Log P: 3.2601085
• 摩尔折射率: 81.5039 cm^3
• 极化性: 31.87077 Å^3
• 极化表面积: 84.08 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: 2.95
• LOG S: -3.88
• 溶解度: 3.87e-02 g/l

分子性质

理化性质

• 溶解度: 71.3 mg/L; DMSO
• 外观: White Solid
• 熔点: >273°C (dec.); 304 - 306°C
• 疏水性(logP): 2.8; 3.077

安全信息

• 保存条件: Refrigerator
• RTECS编号: EY8600000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 生物活性机理: Glucose uptake inhibitor; Microtubule inhibitor

产品相关信息

• 纯度: ≥98% (NT/TLC); 95%; 98%
• 级别: VETRANAL™, analytical standard
• 应用领域: Broad-spectrum anthelmintic
• Empirical Formula (Hill Notation): C16H13N3O3

详细说明

DrugBank - DB00643

• Drug Groups: approved
• Description: A benzimidazole that acts by interfering with carbohydrate metabolism and inhibiting polymerization of microtubules. [PubChem]
• Indication: For the treatment of Enterobius vermicularis (pinworm), Trichuris trichiura (whipworm), Ascaris lumbricoides (common roundworm), Ancylostoma duodenale (common hookworm), Necator americanus (American hookworm) in single or mixed infections.
• Pharmacology: Mebendazole is a (synthetic) broad-spectrum anthelmintic. The principal mode of action for Mebendazole is by its inhibitory effect on tubulin polymerization which results in the loss of cytoplasmic microtubules.
• Toxicity: Acute oral toxicity (LD₅₀): 620 mg/kg [Mouse]. Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.
• Affected Organisms: Helminthic Microorganisms
• Biotransformation: Primarily hepatic. Primary metabolite is 2-amino-5-benzoylbenzimidazole, but also metabolized to inactive hydroxy and hydroxyamino metabolites. All metabolites are devoid of anthelmintic activity.
• Absorption: Poorly absorbed (approximately 5 to 10%) from gastrointestinal tract. Fatty food increases absorption.
• Half Life: 2.5 to 5.5 hours (range 2.5 to 9 hours) in patients with normal hepatic function. Approximately 35 hours in patients with impaired hepatic function (cholestasis).
• Protein Binding: 90-95%
• Elimination: In man, approximately 2% of administered mebendazole is excreted in urine and the remainder in the feces as unchanged drug or a primary metabolite.
• References: [Link]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 46404

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M200500

Anthelmintic (Nematodes).

参考文献

• Link
• Al-Badr, A.A., et al.: Anal. Profiles Drug Subs., 16, 291 (1987)