methyl N-[5-(propane-1-sulfonyl)-1H-1,3-benzodiazol-2-yl]carbamate

• ChemBase编号: 157693
• 分子式: C12H15N3O4S
• 平均质量: 297.3302
• 单一同位素质量: 297.07832698
• SMILES: CCCS(=O)(=O)c1ccc2c(c1)nc([nH]2)NC(=O)OC
• Canonical SMILES: CCCS(=O)(=O)c1ccc2c(c1)nc([nH]2)NC(=O)OC
• InChI: InChI=1S/C12H15N3O4S/c1-3-6-20(17,18)8-4-5-9-10(7-8)14-11(13-9)15-12(16)19-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
• InChIKey: CLSJYOLYMZNKJB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl N-[5-(propane-1-sulfonyl)-1H-1,3-benzodiazol-2-yl]carbamate
• IUPAC传统名: methyl N-[5-(propane-1-sulfonyl)-1H-1,3-benzodiazol-2-yl]carbamate
• 别名: 阿苯达唑砜; Methyl [5-(propylsulfonyl)-1H-benzimidazol-2-yl]carbamate; Albendazole sulfone; Methyl 5-n-propylsulfonyl-2-benzimidazolecarbamate; N-[6-(Propylsulfonyl)-1H-benzimidazol-2-yl]carbamic Acid Methyl Ester; Methyl [5-(propylsulfonyl)-1H-benzimidazol-2-yl]carbamate, Albendazole Impurity C (EP),; Albendazole Sulfone; Alben; Bermosol; Eskazole; Helmintal; Valbazen; Zentel

登记号

• CAS号: 75184-71-3
• MDL号: MFCD00600775
• Beilstein号: 8394880
• PubChem SID: 162251830
• PubChem CID: 53174

理论计算性质

• Acid pKa: 8.719393
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 1.6716211
• LogD (pH = 7.4): 1.6547793
• Log P: 1.6725836
• 摩尔折射率: 74.1216 cm^3
• 极化性: 29.929394 Å^3
• 极化表面积: 101.15 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO
• 外观: Yellow Solid
• 熔点: 290-292°C; 296-298°C (dec.)

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: DD6520700
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63; 63-36/38
• 安全公开号: 26-36/37; 36/37
• TSCA收录: 否
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H315-H319-H361d; H361
• GHS警示性声明: P281-P201-P202-P308+P313-P405-P501A; P281-P305 + P351 + P338

药理学性质

• 生物活性机理: Also has been shown to inhibit the enzyme fumarate reductase, which is helminth-specific.; Causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin,; Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP),; Due to diminished energy production, the parasite is immobilized and eventually dies.; The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores.; This action may be considered secondary to the effect; thus inhibiting its polymerization or assembly into microtubules.; which is the energy required for the survival of the helminth.

产品相关信息

• 级别: VETRANAL™, analytical standard
• 应用领域: Anthelmintic; Investigated for treatment of chronic stronglyoidiasis, and for microsporidiosis in AIDS patients
• Empirical Formula (Hill Notation): C12H15N3O4S

详细说明

Sigma Aldrich - 35394

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A511615

A metabolite of Albendazole, an anthelmintic.

参考文献

• Dominguez, L., et al.: Farmaco, 50, 697 (1995)
• De Laurentis, N., et al.: Pharm. Pharmacol. Lett., 6, 2: 51 (1996)
• U.S. Pat., 1975, SmithKline, 3 915 986; CA, 84, 31074r, (synth, pharmacol)
• Theodorides, V.J. et al., Experientia, 1976, 32, 702, (pharmacol)
• Bogan, J.A., Drugs of Today (Barcelona), 1979, 15, 87, (rev)
• Gyurik, R.J. et al., Drug Metab. Dispos., 1981, 9, 503, (metab)
• Bochis, R.J. et al., J. Med. Chem., 1981, 24, 1518, (props)
• Firth, M., Int. Congr. Symp. Ser. R. Soc. Med., (Ed.), No. 61, 1984, (book)
• Delatour, P. et al., Xenobiotica, 1991, 21, 217, (metab)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 38
• Archibald, L.K. et al., Quart. J. Med., 1993, 86, 191, (use)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 2970, (synonyms)
• Oldfield, E.C., Am. J. Gastroenterol., 1995, 90, 159, (use)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VAD000