Glisoxepide
-
Glisoxepide
structure -
-
CAS No:
25046-79-1
-
Formula:
C20H27N5O5S
-
Chemical Name:
Glisoxepide
-
Synonyms:
3-Isoxazolecarboxamide,N-[2-[4-[[[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-;Urea,1-(hexahydro-1H-azepin-1-yl)-3-[[p-[2-(5-methyl-3-isoxazolecarboxamido)ethyl]phenyl]sulfonyl]-;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;RP 22410;Glisoxepide;BS 4231;Glisoxepid;Pro-Diaban;Glisepin;Pro-Diaben;12626-35-6;35340-75-1
-
CAS No:
Description
Solid
Glisoxepide is a sulfonamide.|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.|Glisoxepide is a second-generation sulfonylurea with antihyperglycemic activity. Like other second-generation compounds, glisoxepide exerts greater binding affinity than the first-generation compounds. Glisoxepide shows peroxisome proliferator-activated receptor (PPAR) gamma agonistic activity, has a short half-life and is excreted in both the bile and urine.
Glisoxepide Basic Attributes
449.52400
449.52
246-579-5
H7SC0I332I
DTXSID9023097
C72801
A - Alimentary tract and metabolism
Drug Information
For the treatment of diabetes mellitus type 2.
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.
Glisoxepide is a hypoglycemic sulphonylurea agent. The sulphonylureas are a family of drugs based on a common sulphonylurea core. These drugs act via augmentation of secretion of insulin from pancreatic beta-cells. Sulphonylureas may also cause a reduction in serum glucagon and potentiate the action of insulin at the extrapancreatic tissues. Glisoxepide functions as a non-selective K(ATP) channel blocker. It is thought to stimulate insulin secretion by closing the ATP-sensitive K(+) (K(ATP)) channels (Kir6.2/SUR1 complex, KATP channels) in pancreatic beta-cells. This inhibits a tonic, hyperpolarizing efflux of potassium, thus causing the electric potential over the membrane to become more positive. This depolarization opens voltage-gated Ca2+ channels. The rise in intracellular calcium leads to increased fusion of insulin granulae with the cell membrane, and therefore increased secretion of (pro)insulin.
4-(4-beta-(5-methylisoxazol-3-carboxamidoethyl)phenylsulfonyl)-1,1-hexamethylenesemicarbazide
Computed Properties
Molecular Weight:449.5
XLogP3:2.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:7
Exact Mass:449.17329015
Monoisotopic Mass:449.17329015
Topological Polar Surface Area:142
Heavy Atom Count:31
Complexity:697
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Request for Quotation