Details of the Drug

General Information of Drug (ID: DMJPR2B)

Drug Name

Glisoxepide

Synonyms

Glisepin; Glisoxepid; Glisoxepida; Glisoxepidum; Glisoxepida [Spanish]; BS 4231; Bay B 4231; FBB 4231; RP22410; Glisoxepida [INN-Spanish]; Glisoxepide (INN); Glisoxepidum [INN-Latin]; Pro-Diaban; Glisoxepide [INN:BAN:DCF]; N-[2-[4-(azepan-1-ylcarbamoylsulfamoyl)phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide; N-{2-[4-({[(azepan-1-ylamino)carbonyl]amino}sulfonyl)phenyl]ethyl}-5-methylisoxazole-3-carboxamide; 1-(Hexahydro-1H-azepin-1-yl)-3-((p-(2-(5-methyl-3-isoxazolecarboxamido)ethyl)phenyl)sulfonyl)urea

Indication

Disease Entry	ICD 11	Status	REF
Non-insulin dependent diabetes	5A11	Approved	[1], [2]

Therapeutic Class

Hypoglycemic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

449.5

Topological Polar Surface Area (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H27N5O5S
IUPAC Name: N-[2-[4-(azepan-1-ylcarbamoylsulfamoyl)phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Canonical SMILES: CC1=CC(=NO1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NN3CCCCCC3
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

Cross-matching ID

PubChem CID: 32778
ChEBI ID: CHEBI:135731
CAS Number: 25046-79-1
DrugBank ID: DB01289
TTD ID: D04NTJ
INTEDE ID: DR0780

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Inward rectifier potassium channel Kir1.2 (KCNJ10)	TTG140O	KCJ10_HUMAN	Blocker	[1]

------------------------------------------------------------------------------------

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)_{Main DME}	DE5IED8	CP2C9_HUMAN	Substrate	[3]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	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.
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	Clinically and pharmacologically relevant interactions of antidiabetic drugs. Ther Adv Endocrinol Metab. 2016 Apr;7(2):69-83.
4	Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
5	Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
6	Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
7	Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
8	Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
9	Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
10	New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
11	A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
12	A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
13	Triggering and amplification of insulin secretion by dimethyl alpha-ketoglutarate, a membrane permeable alpha-ketoglutarate analogue. Eur J Pharmacol. 2009 Apr 1;607(1-3):41-6.
14	Effect of the chlorpropamide and fructose-1,6-bisphosphate of soluble TNF receptor II levels. Pharmacol Res. 2004 May;49(5):449-53.
15	Hydroxyl-substituted sulfonylureas as potent inhibitors of specific [3H]glyburide binding to rat brain synaptosomes. Bioorg Med Chem. 2003 May 1;11(9):2099-113.
16	Inhibition of ATP-activated potassium channels exerts pressor effects and improves survival in a rat model of severe hemorrhagic shock. Shock. 1996 Jun;5(6):391-4.
17	Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases. Biochem Pharmacol. 2007 Jun 1;73(11):1842-51.
18	Coupling between proximal tubular transport processes. Studies with ouabain, SITS and HCO3-free solutions. Pflugers Arch. 1977 Apr 25;368(3):245-52.
19	Cardioselective K(ATP) channel blockers derived from a new series of m-anisamidoethylbenzenesulfonylthioureas. J Med Chem. 2001 Mar 29;44(7):1085-98.