1-(4-acetylbenzenesulfonyl)-3-cyclohexylurea

• ChemBase编号: 297
• 分子式: C15H20N2O4S
• 平均质量: 324.3953
• 单一同位素质量: 324.11437813
• SMILES: S(=O)(=O)(NC(=O)NC1CCCCC1)c1ccc(cc1)C(=O)C
• Canonical SMILES: O=C(NS(=O)(=O)c1ccc(cc1)C(=O)C)NC1CCCCC1
• InChI: InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
• InChIKey: VGZSUPCWNCWDAN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(4-acetylbenzenesulfonyl)-3-cyclohexylurea; 3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea
• IUPAC传统名: 1-(4-acetylbenzenesulfonyl)-3-cyclohexylurea; 3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea; acetohexamide
• 商标名: Cyclamide; Dimelin; Dimelor; Dymelor; Gamadiabet; Hypoglicil; Metaglucina; Minoral; Ordimel; Tsiklamid
• 别名: 4-乙酰基-N-[(环己胺基)羰基]苯磺酰胺; 醋磺环己脲; Acetohexamid; Acetohexamide; 4-Acetyl-N-[(cyclohexylamino)-carbonyl]benzenesulfonamide; 4-Acetyl-N-[(cyclohexylamino)carbonyl]benzenesulfonamide; Acetohexamide; Dimelin; Dimelor; Dymelor; Gamadiabet; Hypoglicil; Metaglucina; Minoral; Ordimel; Tsiklamid; U 14812; 1-(p-Acetylbenzenesulfonyl)-3-cyclohexylurea; 1-[(p-Acetylphenyl)sulfonyl]-3-cyclohexylurea; N-(p-Acetylphenylsulfonyl)-N'-cyclohexylurea

登记号

• CAS号: 968-81-0
• EC号: 213-530-4
• MDL号: MFCD00072156
• PubChem SID: 24278077; 160963760; 46505821
• PubChem CID: 1989

理论计算性质

JChem

• Acid pKa: 4.313318
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.040655
• LogD (pH = 7.4): 0.8747415
• Log P: 1.8149334
• 摩尔折射率: 82.7722 cm^3
• 极化性: 32.758297 Å^3
• 极化表面积: 92.34 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.72
• LOG S: -3.83
• 溶解度: 4.83e-02 g/l

分子性质

理化性质

• 溶解度: 3430 mg/L; DMSO: ~45 mg/mL; H2O: insoluble
• 外观: white solid
• 疏水性(logP): 2.7

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: YR7350000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... KCNJ1(3758)

产品相关信息

• 级别: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C15H20N2O4S

详细说明

MP Biomedicals - 02193572

Hypoglycemic agent

DrugBank - DB00414

• Drug Groups: approved
• Description: A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide. [PubChem]
• Indication: Used in the management of diabetes mellitus type 2 (adult-onset).
• Pharmacology: Acetohexamide is an intermediate-acting, first-generation oral sulfonylurea. It lowers blood sugar by stimulating the pancreatic beta cells to secrete insulin and by helping the body use insulin efficiently. The pancreas must produce insulin for this medication to work. Acetohexamide has one-third the potency of chlorpropamide, and twice the potency of tolbutamide; however, similar hypoglycemic efficacy occurs with equipotent dosage of sulfonylureas.
• Toxicity: Oral, rat LD₅₀: 5 gm/kg; Oral, mouse LD₅₀: >2500 mg/kg. Symptoms of an acetohexamide overdose include hunger, nausea, anxiety, cold sweats, weakness, drowsiness, unconsciousness, and coma.
• Affected Organisms: Humans and other mammals
• Biotransformation: Extensively metabolized in the liver to the active metabolite hydroxyhexamide, which exhibits greater hypoglycemic potency than acetohexamide. Hydroxyhexamide is believed to be responsible for prolonged hypoglycemic effects.
• Absorption: Rapidly absorbed from the GI tract.
• Half Life: Elimination half-life of the parent compound is 1.3 hours and the elimination half-life of the active metabolite is approximately 5-6 hours.
• Protein Binding: 90%
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - A178

Biochem/physiol Actions
口服降血糖药
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A178.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A162650

Acetohexamide is a sulfonylurea derivative. Acetohexamide is a hyopglycemic agent with moderate uricosuric activity. Acetohexamide is a first generation medication used in the treatment of diabetes metilus type 2.

参考文献

• Yu, T-F. et al.: Metab. Clin. Exp., 17, 309 (1968)
• Harrower, A.D.B. et al.: Clin. Pharmacokin., 31, 111 (1968)
• Hirota, Y. et al.: Diab. Med., 26, 948 (1968)