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

General Information of Drug (ID: DR0766)
Drug Name
Gemfibrozil
Synonyms
Gemfibril; Gemfibromax; Gemfibrozilo; Gemfibrozilum; Gemlipid; Gemnpid; Gevilon Uno; Hipolixan; Innogen; Ipolipid; Lanaterom; Apo-Gemfibrozil; Ausgem; Bolutol; Brozil; Cholespid; Clearol; Decrelip; Elmogan; Fetinor; Fibratol; Fibrocit; Lifibron; Lipazil; Lipigem; Lipira; Lipizyl; Litarek; Micolip; Normolip; Pilder; Polyxit; Progemzal; Reducel; Regulip; Renabrazin; Sinelip; Synbrozil; Taborcil; Tentroc; Trialmin; WL-Gemfibrozil; gemfibrozil; 25812-30-0; 5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid; CI-719; Gemd; Gozid; Hidil; Jezil; Lipur; Lopid
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 250.33 Topological Polar Surface Area 46.5
Heavy Atom Count 18 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3463
PubChem SID
9232 ; 653082 ; 855780 ; 4651818 ; 7847400 ; 7979382 ; 8149356 ; 8152202 ; 10321602 ; 10852033 ; 11112705 ; 11335313 ; 11360552 ; 11363719 ; 11366281 ; 11368843 ; 11371380 ; 11374103 ; 11377005 ; 11461524 ; 11466242 ; 11467362 ; 11484910 ; 11485884 ; 11488913 ; 11490256 ; 11492377 ; 11494639 ; 11533483 ; 12013353 ; 14798621 ; 17389870 ; 24895377 ; 26611755 ; 26679791 ; 26746993 ; 26746994 ; 26751514 ; 26751515 ; 28325629 ; 29222597 ; 46508264 ; 47290997 ; 47365037 ; 47662123 ; 47885266 ; 48034963 ; 48110314 ; 48184857 ; 48334343
ChEBI ID
ChEBI:5296
CAS Number
25812-30-0
TTD Drug ID
D05VIX
Formula
C15H22O3
Canonical SMILES
CC1=CC(=C(C=C1)C)OCCCC(C)(C)C(=O)O
InChI
1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)
InChIKey
HEMJJKBWTPKOJG-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
Gemfibrozil 1-beta-glucuronide metabolite DM002110
45039339
Conjugation - O-Glucuronidation 1 [6] , [7] , [4]
Gemfibrozil metabolite M1 DM002108
71373063
Oxidation - 5-Hydroxylation 1 [8] , [6] , [3]
Gemfibrozil metabolite M2 DM002111
10445630
Oxidation - 4-Hydroxylation 1 [9] , [10] , [11]
Gemfibrozil metabolite M4 DM002112 N. A. Unclear 1 [12] , [10]
Gemfibrozil metabolite M3 DM002109
88118
Unclear 2 [3] , [10] , [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001124 Gemfibrozil Gemfibrozil metabolite M1 Oxidation - 5-Hydroxylation CYP3A4 [8], [6], [3]
MR001125 Gemfibrozil Gemfibrozil 1-beta-glucuronide metabolite Conjugation - O-Glucuronidation UGT1A1 ... [6], [7], [4]
MR001126 Gemfibrozil Gemfibrozil metabolite M2 Oxidation - 4-Hydroxylation Unclear [9], [10], [11]
MR001127 Gemfibrozil Gemfibrozil metabolite M4 Unclear Unclear [12], [10]
MR001123 Gemfibrozil metabolite M1 Gemfibrozil metabolite M3 Unclear CYP3A4 [3], [10], [11]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol-2,3-dioxygenase (caD) DME1057 Bacillus pumilus
A0A371SLU3_9BACI
1.13.11.2
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 6  DME(s)
References
1 Cerivastatin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Genomic, proteomic, and metabolite characterization of gemfibrozil-degrading organism Bacillus sp. GeD10. Environ Sci Technol. 2016 Jan 19;50(2):744-55.
3 Clinical pharmacokinetics of fibric acid derivatives (fibrates). Clin Pharmacokinet. 1998 Feb;34(2):155-62.
4 The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4.
5 Comprehensive pharmacogenomic study reveals an important role of UGT1A3 in montelukast pharmacokinetics. Clin Pharmacol Ther. 2018 Jul;104(1):158-168.
6 Intracellular pharmacokinetics of gemcitabine, its deaminated metabolite 2',2'-difluorodeoxyuridine and their nucleotides Br J Clin Pharmacol. 2018 Jun;84(6):1279-1289. doi: 10.1111/bcp.13557.
7 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.
8 The metabolism of gemfibrozil Proc R Soc Med. 1976;69 Suppl 2(Suppl 2):11-4.
9 Congenital Zika syndrome in non-endemic regions J Perinat Med. 2018 Sep 25;46(7):819. doi: 10.1515/jpm-2017-0403.
10 Biodegradation of emerging organic pollutant gemfibrozil: Mechanism, kinetics and pathway modelling. Bioresour Technol. 2023 Apr;374:128749. doi: 10.1016/j.biortech.2023.128749.
11 Metabolic Activation of Gemfibrozil Mediated by Cytochrome P450 Enzymes and Sulfotransferases. Chem Res Toxicol. 2022 Jul 18;35(7):1257-1266. doi: 10.1021/acs.chemrestox.2c00054.
12 Gemfibrozil metabolite inhibits in vitro low-density lipoprotein (LDL) oxidation and diminishes cytotoxicity induced by oxidized LDL Metabolism. 2000 Apr;49(4):479-85. doi: 10.1016/s0026-0495(00)80012-8.

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