Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0775)
Drug Name
Glibenclamide
Synonyms
Gewaglucon; Gilemal; Glibenbeta; Glibenclamide; Glibenclamidum; Glibenil; Glibens; Glibil; Glimel; Glimide; Glucohexal; Glucolon; Glucoremed; Glybenclamide; Glybenzcyclamide; Glynase; Apo-Glibenclamide; Azuglucon; Bastiverit; Benclamin; Betanase; Daonil; Diabeta; Dibelet; Duraglucon; Euglucan; Euglucon; Euglucon 5; Euglykon; Hexaglucon; Humedia; Libanil; Lisaglucon; Maninil; Med-Glionil; Micronase; Neogluconin; Normoglucon; Orabetic; Praeciglucon; Prodiabet; Renabetic; Semi-daonil; Suraben; Tiabet; Yuglucon; glyburide; 10238-21-8; Adiab; Melix; Pira
Indication Diabetes mellitus [ICD11: 5A10] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 494 Topological Polar Surface Area 122
Heavy Atom Count 33 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3488
PubChem SID
9234 ; 855894 ; 3146598 ; 5047958 ; 7847402 ; 7979403 ; 8147024 ; 8150168 ; 8152216 ; 10321542 ; 10502519 ; 11111219 ; 11112597 ; 11113353 ; 11119957 ; 11120445 ; 11120933 ; 11121416 ; 11121896 ; 11147040 ; 11335656 ; 11360895 ; 11362485 ; 11363144 ; 11365047 ; 11365706 ; 11367609 ; 11368268 ; 11370241 ; 11370242 ; 11372372 ; 11373210 ; 11375035 ; 11375771 ; 11376430 ; 11461867 ; 11466344 ; 11467464 ; 11485567 ; 11486267 ; 11489632 ; 11491142 ; 11493013 ; 11494064 ; 14835352 ; 17405062 ; 22391414 ; 24277838 ; 24895097 ; 26542333
ChEBI ID
ChEBI:5441
CAS Number
10238-21-8
TTD Drug ID
D05LYX
Formula
C23H28ClN3O5S
Canonical SMILES
COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
InChI
1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
InChIKey
ZNNLBTZKUZBEKO-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2-trans-hydroxycyclohexyl glyburide DM006690
131770000
Oxidation - Aliphatic hydroxylation 1 [6] , [4]
3-cis-Hydroxycyclohexyl glyburide DM006695
91810507
Oxidation - Aliphatic hydroxylation 1 [6] , [4] , [7]
3-trans-Hydroxycyclohexyl glyburide DM006692
97289675
Oxidation - Aliphatic hydroxylation 1 [6] , [4]
4-cis-hydroxycyclohexyl glyburide DM006691
3082214
Oxidation - Aliphatic hydroxylation 1 [6] , [4] , [7]
4-cis-hydroxycyclohexyl glyburide DM006691
3082214
Oxidation - Aliphatic hydroxylation 1 [6] , [4]
Ethylhydroxycyclohexyl glyburide DM006693 N. A. Oxidation - Aliphatic hydroxylation 1 [6] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007218 Glibenclamide 2-trans-hydroxycyclohexyl glyburide Oxidation - Aliphatic hydroxylation CYP3A4 ... [6], [4]
MR007219 Glibenclamide 4-cis-hydroxycyclohexyl glyburide Oxidation - Aliphatic hydroxylation CYP3A4 ... [6], [4]
MR007220 Glibenclamide 3-trans-Hydroxycyclohexyl glyburide Oxidation - Aliphatic hydroxylation CYP3A4 ... [6], [4]
MR007221 Glibenclamide Ethylhydroxycyclohexyl glyburide Oxidation - Aliphatic hydroxylation CYP3A4 ... [6], [4]
MR007222 Glibenclamide 3-cis-Hydroxycyclohexyl glyburide Oxidation - Aliphatic hydroxylation CYP3A4 ... [6], [4], [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
⏷ Show the Full List of 6  DME(s)
References
1 ClinicalTrials.gov (NCT02145611) Vildagliptin vs. Glibenclamide in Endothelial Function in Type 2 Diabetes and Hypertension.
2 Contributions of human cytochrome P450 enzymes to glyburide metabolism. Biopharm Drug Dispos. 2010 May;31(4):228-42.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
4 Identification of CYP3A7 for glyburide metabolism in human fetal livers. Biochem Pharmacol. 2014 Dec 15;92(4):690-700.
5 Contribution of UDP-glucuronosyltransferases 1A9 and 2B7 to the glucuronidation of indomethacin in the human liver. Eur J Clin Pharmacol. 2007 Mar;63(3):289-96.
6 Kinetics of glyburide metabolism by hepatic and placental microsomes of human and baboon
7 Identification of glyburide metabolites formed by hepatic and placental microsomes of humans and baboons

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