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

General Information of Drug (ID: DR0688)
Drug Name
Fenofibrate
Prodrug Info Fenofibrate is the prodrug of Fenofibric acid
Synonyms
Fenobrate; Fenofibrato; Fenofibrato [INN-Spanish]; Fenofibratum; Fenofibratum [INN-Latin]; Fenogal; Fenoglide; Fenotard; Finofibrate; LF-178; Lipanthyl; Lipantil; Lipantil (TN); Lipidex; Lipidil; Lipifen; Lipirex; Lipoclar; Lipofen; Lipofene; Liposit; Ankebin; Antara; Elasterate; Elasterin; Lipsin; Lofibra; Luxacor; Nolipax; Procetofen; Procetofene; Proctofene; Protolipan; Secalip; Sedufen; TRICOR (MICRONIZED); Tricor; Tricor (TN); Triglide; fenofibrate; 49562-28-9; Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 360.8 Topological Polar Surface Area 52.6
Heavy Atom Count 25 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3339
PubChem SID
9788 ; 143271 ; 855565 ; 3718278 ; 5309234 ; 7847631 ; 7979221 ; 8149697 ; 8152122 ; 10321317 ; 10852041 ; 11111181 ; 11111182 ; 11335732 ; 11360971 ; 11364144 ; 11366706 ; 11369268 ; 11372481 ; 11373845 ; 11377430 ; 11461943 ; 11466303 ; 11467423 ; 11485116 ; 11486105 ; 11489206 ; 11491246 ; 11492228 ; 11495064 ; 11528711 ; 11533532 ; 14901407 ; 17405049 ; 22395205 ; 24278015 ; 26612151 ; 26680406 ; 26746914 ; 26746915 ; 26751450 ; 29222474 ; 46507371 ; 47291103 ; 47291104 ; 47365158 ; 47515293 ; 47662254 ; 47736448 ; 47810726
ChEBI ID
ChEBI:5001
CAS Number
49562-28-9
TTD Drug ID
D07XGR
Formula
C20H21ClO4
Canonical SMILES
CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)Cl
InChI
1S/C20H21ClO4/c1-13(2)24-19(23)20(3,4)25-17-11-7-15(8-12-17)18(22)14-5-9-16(21)10-6-14/h5-13H,1-4H3
InChIKey
YMTINGFKWWXKFG-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
Fenofibric acid DM003108
64929
Hydrolysis - Hydrolysis 1 [3] , [7] , [8] , [9]
Fenofibrate metabolite X DM000166
146594199
Conjugation - Methylation 2 [10]
Fenofibryl glucuronide DM000165
10028724
Conjugation - Glucuronidation 2 [11]
Reduced Fenofibric Acid DM000163
68715
Reduction - Reduction 2 [12]
Reduced Fenofibric Acid glucuronide DM000164 N. A. Conjugation - O-Glucuronidation 3 [12]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003093 Fenofibrate Fenofibric acid Hydrolysis - Hydrolysis CES1 [3], [7], [8], [9]
MR003094 Fenofibric acid Reduced Fenofibric Acid Reduction - Reduction CBR1 ... [12]
MR003095 Fenofibric acid Fenofibryl glucuronide Conjugation - Glucuronidation UGT1A9 [11]
MR003096 Fenofibric acid Fenofibrate metabolite X Conjugation - Methylation Unclear [10]
MR003092 Reduced Fenofibric Acid Reduced Fenofibric Acid glucuronide Conjugation - O-Glucuronidation UGT1A9 [12]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1B1 (AKR1B1) DME0087 Homo sapiens
ALDR_HUMAN
1.1.1.21
[2]
Aldo-keto reductase 1C1 (AKR1C1) DME0197 Homo sapiens
AK1C1_HUMAN
1.1.1.149
[2]
Aldo-keto reductase 1C2 (AKR1C2) DME0233 Homo sapiens
AK1C2_HUMAN
1.1.1.357
[2]
Aldo-keto reductase 1C3 (AKR1C3) DME0118 Homo sapiens
AK1C3_HUMAN
1.1.1.357
[2]
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[5]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1406 Collinsella aerofaciens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [6]
⏷ Show the Full List of 15  DME(s)
References
1 Fenofibrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In?vitro metabolism of fenofibric acid by carbonyl reducing enzymes Chem Biol Interact. 2016 Oct 25;258:153-8. doi: 10.1016/j.cbi.2016.09.001.
3 The role of human carboxylesterases in drug metabolism: have we overlooked their importance? Pharmacotherapy. 2013 Feb;33(2):210-22. doi: 10.1002/phar.1194.
4 Clinical pharmacokinetics of fibric acid derivatives (fibrates). Clin Pharmacokinet. 1998 Feb;34(2):155-62.
5 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 Predicting the environmental emissions arising from conventional and nanotechnology-related pharmaceutical drug products. Environ Res. 2021 Jan;192:110219. doi: 10.1016/j.envres.2020.110219.
8 The Hyperlipidaemic Drug Fenofibrate Significantly Reduces Infection by SARS-CoV-2 in Cell Culture Models. Front Pharmacol. 2021 Aug 6;12:660490. doi: 10.3389/fphar.2021.660490.
9 Targeting Peroxisome Proliferator-Activated Receptor- (PPAR- ) to reduce paclitaxel-induced peripheral neuropathy. Brain Behav Immun. 2021 Mar;93:172-185. doi: 10.1016/j.bbi.2021.01.004.
10 Fenofibrate: metabolism and species differences for peroxisome proliferation in cultured hepatocytes Fundam Appl Toxicol. 1995 Jun;26(1):63-74. doi: 10.1006/faat.1995.1075.
11 The UDP-glucuronosyltransferase 1A9 enzyme is a peroxisome proliferator-activated receptor alpha and gamma target gene. J Biol Chem. 2003 Apr 18;278(16):13975-83.
12 In vitro metabolism of fenofibric acid by carbonyl reducing enzymes. Chem Biol Interact. 2016 Oct 25;258:153-8.

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