1-(4-acetylbenzenesulfonyl)-3-cyclohexylurea

• ChemBase ID: 297
• Molecular Formular: C15H20N2O4S
• Molecular Mass: 324.3953
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-acetylbenzenesulfonyl)-3-cyclohexylurea; 3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea
• IUPAC Traditional name: 1-(4-acetylbenzenesulfonyl)-3-cyclohexylurea; 3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea; acetohexamide
• Brand Name: Cyclamide; Dimelin; Dimelor; Dymelor; Gamadiabet; Hypoglicil; Metaglucina; Minoral; Ordimel; Tsiklamid
• Synonyms: 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; 4-乙酰基-N-[(环己胺基)羰基]苯磺酰胺; 醋磺环己脲

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.313318
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.040655
• LogD (pH = 7.4): 0.8747415
• Log P: 1.8149334
• Molar Refractivity: 82.7722 cm^3
• Polarizability: 32.758297 Å^3
• Polar Surface Area: 92.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.72
• LOG S: -3.83
• Solubility (Water): 4.83e-02 g/l

PROPERTIES

Physical Property

• Solubility: 3430 mg/L; DMSO: ~45 mg/mL; H2O: insoluble
• Apperance: white solid
• Hydrophobicity(logP): 2.7

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: YR7350000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... KCNJ1(3758)

Product Information

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

DETAILS

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
Oral hypoglycemic agent
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.

REFERENCES

• 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)