Glisoxepide
Basic information
- CAS
25046-79-1- Standard SMILES
Cc1cc(C(=O)NCCc2ccc(S(=O)(=O)NC(=O)NN3CCCCCC3)cc2)no1- InChIKey
ZKUDBRCEOBOWLF-UHFFFAOYSA-N- Molecular formula
- C20H27N5O5S
- Average molar mass
- 449.5 g/mol
- Monoisotopic mass
- 449.17329015
Overview
Glisoxepide is a sulfonamide.
Names & identifiers
- Preferred name
- Glisoxepide
- IUPAC
- N-[2-[4-(azepan-1-ylcarbamoylsulfamoyl)phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
- English name
- glisoxepide
- Molecular formula
- C20H27N5O5S
- Molecular weight
- 449.529
Names & synonyms
GlisoxepideGlisoxepid25046-79-1GlisoxepidaGlisoxepidumBay B 4231FBB 4231RP 22410DTXSID9023097FBB-4231H7SC0I332IRP-22410
Show more names
Pro-DiabanBAY B-4231Glisoxepid (10mM in DMSO)N-[2-[4-(azepan-1-ylcarbamoylsulfamoyl)phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide3-Isoxazolecarboxamide, N-[2-[4-[[[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-Pivaloyloxymethyl [2S-(2?,5?,6?)]-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrochloride
BAY-B-4231DTXCID803097N-{2-[4-({[(azepan-1-yl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-5-methyl-1,2-oxazole-3-carboxamideN-(2-(4-((((azepan-1-yl)carbamoyl)amino)sulfonyl)phenyl)ethyl)-5-methyl-1,2-oxazole-3-carboxamideRefChem:143393A10BB11246-579-54-(4-beta-(5-methylisoxazol-3-carboxamidoethyl)phenylsulfonyl)-1,1-hexamethylenesemicarbazide
Database identifiers
- CAS
25046-79-1- PubChem CID
- 32778
- DTXSID
DTXSID9023097- ChEMBL
CHEMBL2106618- ChEBI
CHEBI:135731- UNII
- H7SC0I332I
- EC Number
- 246-579-5
- Nikkaji
- J20.337H
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 142 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 7
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 697
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility1.03e-01 g/L
Melting Point189 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 189 ° · 189°
- Density
- 1.2348 · 1.2348 (rough estimate)
- refractive index
- 1.646 · 1.6460 (estimate)
- storage temp.
- Refrigerator
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
- form
- Solid
- pka
- 5.92 · 5.92±0.10(Predicted)
- color
- Pale Yellow to Yellow
- FDA UNII
- 7 SC0I332I · H7SC0I332I
- NCI Drug Dictionary
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 in mice, rats, cats, dogs (g/kg): >10.0, >10.0, >4.0, >2.0 orally; in mice, rats (mg/kg): 283, 196 i.v. (Tettenborn)
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
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.
Mechanism of Action
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.
Cellular LocationsMembrane
Applications
UsesLabelled Glisoxepid (G410600). Glisoxepid is used as an antidiabetic drug. Glisoxepid is a sulfonylurea derivative used in the treatment of diabetes mellitus type 2.
Upstream & downstream products
Upstream raw materials
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