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

General Information of Drug (ID: DR0583)
Drug Name
Enzalutamide
Synonyms
Enzalutamide; Enzalutamide (MDV3100); MDV 3100; MDV-3100; MDV3100; MDV3100 (Enzalutamide); MDV3100 Enzalutamide; XTANDI; 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide; 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl}-2-fluoro-N-methylbenzamide; 915087-33-1; 93T0T9GKNU; CHEBI:68534; UNII-93T0T9GKNU
Indication Prostate cancer [ICD11: 2C82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 464.4 Topological Polar Surface Area 109
Heavy Atom Count 32 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
15951529
PubChem SID
22422973 ; 26557832 ; 33334455 ; 85286065 ; 99437051 ; 103756429 ; 124757115 ; 125163919 ; 125299336 ; 125749051 ; 126731384 ; 131480739 ; 135261179 ; 135684120 ; 135727393 ; 136367372 ; 136367882 ; 136375508 ; 137009352 ; 137275964 ; 143499468 ; 144116190 ; 151990441 ; 152237529 ; 152258872 ; 152344309 ; 160645896 ; 160647721 ; 160821662 ; 162011754 ; 162036208 ; 162196987 ; 163091639 ; 163312249 ; 164041953 ; 164154607 ; 164193917 ; 164761729 ; 165245624 ; 172093747 ; 172914062 ; 174477518 ; 174531457 ; 175267791 ; 175427141 ; 177748753 ; 178103418 ; 185989448 ; 188899565 ; 198993053
ChEBI ID
ChEBI:68534
CAS Number
915087-33-1
TTD Drug ID
D0M1YR
Formula
C21H16F4N4O2S
Canonical SMILES
CC1(C(=O)N(C(=S)N1C2=CC(=C(C=C2)C(=O)NC)F)C3=CC(=C(C=C3)C#N)C(F)(F)F)C
InChI
1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)
InChIKey
WXCXUHSOUPDCQV-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
Carboxyl metabolite enzalutamide (M1) DM017111 N. A. Multi-steps Reaction - Amide Hydrolysis; Demethylation 1 [8] , [9]
Enzalutamide metabolite M13 DM017113 N. A. Unclear 1 [8]
Enzalutamide metabolite M4 DM016122
46898524
Unclear 1 [8]
Enzalutamide metabolite M6 DM006404
156596418
Oxidation - Hydroxylation 1 [9] , [10]
Enzalutamide metabolite M1 DM006406
46898522
Unclear 2 [8]
Enzalutamide metabolite M11 DM017112 N. A. Conjugation - Acyl glucuronide conjugation 2 [8]
Enzalutamide metabolite M14 DM017114 N. A. Conjugation - Cysteinylglycine conjugation 2 [8]
Enzalutamide metabolite M3 DM016121
46898523
Unclear 2 [8]
N-desmethyl enzalutamide DM006405
70678916
Oxidation - Demethylation 2 [8]
Carboxyl metabolite enzalutamide (M1) DM017111 N. A. Unclear 3 [8] , [9]
Enzalutamide metabolite M12 DM017118 N. A. Conjugation - Acyl glucuronide conjugation 3 [8]
Enzalutamide metabolite M15 DM017115 N. A. Conjugation - Cysteine conjugation 3 [8]
Enzalutamide metabolite M17 DM017117 N. A. Conjugation - Taurine conjugation 3 [8]
Enzalutamide metabolite M11 DM017112 N. A. Conjugation - Acyl glucuronide conjugation 4 [8]
Enzalutamide metabolite M16 DM017116 N. A. Conjugation - Acetylcysteine conjugation 4 [8]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013681 Enzalutamide Enzalutamide metabolite M6 enzalutamide Oxidation - Hydroxylation CYP3A4 ... [9], [10]
MR013685 Indocyanine green Enzalutamide metabolite M13 Unclear Unclear [8]
MR013689 Indocyanine green Carboxyl metabolite enzalutamide (M1) Multi-steps Reaction - Amide Hydrolysis; Demethylation CES1 [8], [9]
MR013693 Indocyanine green Enzalutamide metabolite M4 Unclear Unclear [8]
MR013690 Carboxyl metabolite enzalutamide (M1) Enzalutamide metabolite M5 Unclear Unclear [8]
MR013686 Enzalutamide metabolite M13 Enzalutamide metabolite M14 Conjugation - Cysteinylglycine conjugation Unclear [8]
MR013694 Enzalutamide metabolite M4 Enzalutamide metabolite M5 Unclear Unclear [8]
MR013695 Enzalutamide metabolite M4 Enzalutamide metabolite M3 Unclear Unclear [8]
MR013682 Enzalutamide metabolite M6 enzalutamide N-desmethyl enzalutamide Oxidation - Demethylation CYP2C8 [8]
MR013687 Enzalutamide metabolite M14 Enzalutamide metabolite M15 Conjugation - Cysteine conjugation Unclear [8]
MR013691 Enzalutamide metabolite M5 Enzalutamide metabolite M17 Conjugation - Taurine conjugation Unclear [8]
MR013692 Enzalutamide metabolite M5 Enzalutamide metabolite M12 Conjugation - Acyl glucuronide conjugation Unclear [8]
MR013683 N-desmethyl enzalutamide Carboxyl metabolite enzalutamide (M1) Unclear CES1 ... [8], [9]
MR013684 Carboxyl metabolite enzalutamide (M1) Enzalutamide metabolite M11 Conjugation - Acyl glucuronide conjugation Unclear [8]
MR013688 Enzalutamide metabolite M15 Enzalutamide metabolite M16 Conjugation - Acetylcysteine conjugation Unclear [8]
⏷ Show the Full List of 15 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 7  DME(s)
References
1 Enzalutamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 DrugBank(Pharmacology-Metabolism):Enzalutamide
3 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
4 [Enzalutamide in castration resistant prostate cancer.]
5 Enzalutamide: an evidence-based review of its use in the treatment of prostate cancer. Core Evid. 2013;8:27-35.
6 Pharmacokinetic drug interaction studies with enzalutamide. Clin Pharmacokinet. 2015 Oct;54(10):1057-69.
7 Product Monograph of Xtandi.
8 Absorption, Distribution, Metabolism, and Excretion of the Androgen Receptor Inhibitor Enzalutamide in Rats and Dogs
9 Pharmacokinetic Aspects of the Two Novel Oral Drugs Used for Metastatic Castration-Resistant Prostate Cancer: Abiraterone Acetate and Enzalutamide
10 Clinical Pharmacokinetic Studies of Enzalutamide

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