N-{2-[4-({[(azepan-1-yl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-5-methyl-1,2-oxazole-3-carboxamide

• ChemBase编号: 1144
• 分子式: C20H27N5O5S
• 平均质量: 449.52388
• 单一同位素质量: 449.17328999
• SMILES: S(=O)(=O)(NC(=O)NN1CCCCCC1)c1ccc(CCNC(=O)c2noc(c2)C)cc1
• Canonical SMILES: Cc1onc(c1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NN1CCCCCC1
• InChI: InChI=1S/C20H27N5O5S/c1-15-14-18(23-30-15)19(26)21-11-10-16-6-8-17(9-7-16)31(28,29)24-20(27)22-25-12-4-2-3-5-13-25/h6-9,14H,2-5,10-13H2,1H3,(H,21,26)(H2,22,24,27)
• InChIKey: ZKUDBRCEOBOWLF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-{2-[4-({[(azepan-1-yl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-5-methyl-1,2-oxazole-3-carboxamide
• IUPAC传统名: glisoxepide
• 别名: Glisoxepide; N-[2-[4-[[[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-3-isoxazolecarboxamide; 4-[4-[β-(5-Methylisoxazole-3-carboxamido)ethyl]phenylsulfonyl]-1,1-hexamethylenesemicarbazide; BS 4231; Glisepin; Glisoxepide; Pro-Diaban; Pro-Diaben; RP 22410; Glisoxepid

登记号

• CAS号: 25046-79-1
• PubChem SID: 46508780; 160964607
• PubChem CID: 32778

理论计算性质

JChem

• Acid pKa: 4.066667
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): 0.59831023
• LogD (pH = 7.4): 0.49457988
• Log P: 1.4359764
• 摩尔折射率: 115.8573 cm^3
• 极化性: 44.381973 Å^3
• 极化表面积: 133.64 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.57
• LOG S: -3.64
• 溶解度: 1.03e-01 g/l

详细说明

DrugBank - DB01289

• Drug Groups: approved
• Description: Glisoxepide is one of the sulphonamide-derived oral antidiabetic drugs. It inhibits the uptake of bile acids into isolated rat hepatocytes. However it inhibits taurocholate uptake only in the absence of sodium ions. Glisoxepide uptake could be further inhibited by blockers of the hepatocellular monocarboxylate transporter, by the loop diuretic bumetanide, by 4,4'-diisothiocyano-2,2'-stilbenedisulfonate (DIDS) and by sulphate. These results are consistent with the transport of glisoxepide via the transport system for the unconjugated bile acid cholate.; (PMID:1618280, 9017793)
• Indication: For the treatment of diabetes mellitus type 2.
• Pharmacology: Glisoxepide is a sulfonylurea agent. It stimulates beta cells of the islet of Langerhans in the pancreas to release insulin. It also enhances peripheral insulin sensitivity. Overall it potentiates insulin release and improves insulin dynamics.

Toronto Research Chemicals - G410600

Glisoxepid is used as an antidiabetic drug. Glisoxepid is a sulfonylurea derivative used in the treatment of diabetes mellitus type 2.

参考文献

• Drees, J., et al.: Clin. Chem., 55, 126 (2003)
• Schulz, M., et al.: Pharmazie, 58, 447 (2003)
• Viswanathan, C., et al.: Pharm. Res., 24, 1962 (2003)