Tìm theo
Glisoxepide
Các tên gọi khác (5 ) :
  • BAY-b-4231
  • FBB-4231
  • Glisoxepide
  • RP-22410
  • SID144205252
Thuốc Gốc
Small Molecule
CAS: 25046-79-1
ATC: A10BB11
CTHH: C20H27N5O5S
PTK: 449.524
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)
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C20H27N5O5S
Phân tử khối
449.524
Monoisotopic mass
449.173289689
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)
InChI Key
InChIKey=ZKUDBRCEOBOWLF-UHFFFAOYSA-N
IUPAC Name
N-{2-[4-({[(azepan-1-yl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-5-methyl-1,2-oxazole-3-carboxamide
Traditional IUPAC Name
N-[2-(4-{[(azepan-1-yl)carbamoyl]aminosulfonyl}phenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
SMILES
CC1=CC(=NO1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1
Độ tan chảy
189 °C
Độ hòa tan
1.03e-01 g/l
logP
1.44
logS
-3.6
pKa (strongest acidic)
4.07
pKa (Strongest Basic)
1.59
PSA
133.64 Å2
Refractivity
115.86 m3·mol-1
Polarizability
46.83 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
6
H Bond Donor Count
3
Physiological Charge
-1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
MDDR-Like Rule
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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) 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.
Chỉ Định : For the treatment of diabetes mellitus type 2.
Tương Tác Thuốc :
  • Acebutolol The beta-blocker, acebutolol, may decrease symptoms of hypoglycemia.
  • Acetylsalicylic acid Acetylsalicylic acid increases the effect of the sulfonylurea, glisoxepide.
  • Atenolol The beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
  • Bisoprolol The beta-blocker, bisoprolol, may decrease symptoms of hypoglycemia.
  • Carvedilol The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
  • Chloramphenicol Chloramphenicol may increase the effect of sulfonylurea, glisoxepide.
  • Clofibrate Clofibrate may increase the effect of sulfonylurea, glisoxepide.
  • Esmolol The beta-blocker, esmolol, may decrease symptoms of hypoglycemia.
  • Labetalol The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Metoprolol The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Nadolol The beta-blocker, nadolol, may decrease symptoms of hypoglycemia.
  • Oxprenolol The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
  • Phenylbutazone Phenylbutazone increases the effect of the hypoglycemic agent
  • Pindolol The beta-blocker, pindolol, may decrease symptoms of hypoglycemia.
  • Propranolol The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
  • Rifampicin Rifampin may decrease the effect of sulfonylurea, glisoxepide.
  • Timolol The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty : Farmades
    Sản phẩm biệt dược : Glucoben
  • Công ty : Bayer
    Sản phẩm biệt dược : Glysepin
  • Công ty : Bayer
    Sản phẩm biệt dược : Pro-Diaban
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01289
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=32778
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508780
ChemSpider
http://www.chemspider.com/Chemical-Structure.30380.html
PharmGKB
http://www.pharmgkb.org/drug/PA164743233
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