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Accession NumberDB01289
Typesmall molecule

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)

SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number25046-79-1
WeightAverage: 449.524
Monoisotopic: 449.173289689
Chemical FormulaC20H27N5O5S
Mass SpecNot Available
KingdomOrganic Compounds
ClassBenzene and Substituted Derivatives
Direct parentBenzenesulfonamides
Alternative parentsPhenethylamines; Sulfonylureas; Azepanes; Semicarbazides; Isoxazoles; Sulfonamides; Sulfonyls; Secondary Carboxylic Acid Amides; Enolates; Carboxylic Acids; Polyamines
Substituentsazepane; sulfonylurea; sulfonamide; azole; isoxazole; sulfonic acid derivative; sulfonyl; semicarbazide; carboxamide group; secondary carboxylic acid amide; enolate; polyamine; carboxylic acid derivative; carboxylic acid; amine; hydrazine derivative; organonitrogen compound
Classification descriptionThis compound belongs to the benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
IndicationFor the treatment of diabetes mellitus type 2.
PharmacodynamicsGlisoxepide 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 actionGlisoxepide 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9787
Blood Brain Barrier + 0.741
Caco-2 permeable - 0.6772
P-glycoprotein substrate Substrate 0.594
P-glycoprotein inhibitor I Non-inhibitor 0.7578
P-glycoprotein inhibitor II Non-inhibitor 0.9445
Renal organic cation transporter Non-inhibitor 0.8195
CYP450 2C9 substrate Substrate 0.5621
CYP450 2D6 substrate Non-substrate 0.8474
CYP450 3A4 substrate Non-substrate 0.6478
CYP450 1A2 substrate Non-inhibitor 0.9188
CYP450 2C9 substrate Non-inhibitor 0.6091
CYP450 2D6 substrate Non-inhibitor 0.848
CYP450 2C19 substrate Non-inhibitor 0.7913
CYP450 3A4 substrate Non-inhibitor 0.6763
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7438
Ames test Non AMES toxic 0.7018
Carcinogenicity Non-carcinogens 0.7506
Biodegradation Ready biodegradable 0.5877
Rat acute toxicity 1.6845 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7225
hERG inhibition (predictor II) Non-inhibitor 0.6458
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Experimental Properties
melting point189 °CPhysProp
Predicted Properties
water solubility1.03e-01 g/lALOGPS
pKa (strongest acidic)4.07ChemAxon
pKa (strongest basic)1.59ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count3ChemAxon
polar surface area133.64ChemAxon
rotatable bond count6ChemAxon
number of rings3ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
SpectraNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
PubChem Compound32778
PubChem Substance46508780
Therapeutic Targets DatabaseDAP000925
ATC CodesA10BB11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Drug Interactions
AcebutololThe beta-blocker, acebutolol, may decrease symptoms of hypoglycemia.
Acetylsalicylic acidAcetylsalicylic acid increases the effect of the sulfonylurea, glisoxepide.
AtenololThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
BisoprololThe beta-blocker, bisoprolol, may decrease symptoms of hypoglycemia.
CarvedilolThe beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
ChloramphenicolChloramphenicol may increase the effect of sulfonylurea, glisoxepide.
ClofibrateClofibrate may increase the effect of sulfonylurea, glisoxepide.
EsmololThe beta-blocker, esmolol, may decrease symptoms of hypoglycemia.
LabetalolThe beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
MetoprololThe beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
NadololThe beta-blocker, nadolol, may decrease symptoms of hypoglycemia.
OxprenololThe beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
PhenylbutazonePhenylbutazone increases the effect of the hypoglycemic agent
PindololThe beta-blocker, pindolol, may decrease symptoms of hypoglycemia.
PropranololThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
RifampicinRifampin may decrease the effect of sulfonylurea, glisoxepide.
TimololThe beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Food InteractionsNot Available

1. ATP-sensitive inward rectifier potassium channel 8

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor


Name UniProt ID Details
ATP-sensitive inward rectifier potassium channel 8 Q15842 Details


  1. Szewczyk A, Wojcik G, Lobanov NA, Nalecz MJ: The mitochondrial sulfonylurea receptor: identification and characterization. Biochem Biophys Res Commun. 1997 Jan 23;230(3):611-5. Pubmed
  2. Sato T, Costa AD, Saito T, Ogura T, Ishida H, Garlid KD, Nakaya H: Bepridil, an antiarrhythmic drug, opens mitochondrial KATP channels, blocks sarcolemmal KATP channels, and confers cardioprotection. J Pharmacol Exp Ther. 2006 Jan;316(1):182-8. Epub 2005 Sep 20. Pubmed

Drug created on June 28, 2007 09:58 / Updated on September 16, 2013 17:14