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

• ChemBase ID: 1144
• Molecular Formular: C20H27N5O5S
• Molecular Mass: 449.52388
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{2-[4-({[(azepan-1-yl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-5-methyl-1,2-oxazole-3-carboxamide
• IUPAC Traditional name: glisoxepide
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.066667
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.59831023
• LogD (pH = 7.4): 0.49457988
• Log P: 1.4359764
• Molar Refractivity: 115.8573 cm^3
• Polarizability: 44.381973 Å^3
• Polar Surface Area: 133.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.57
• LOG S: -3.64
• Solubility (Water): 1.03e-01 g/l

DETAILS

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.

REFERENCES

• 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)