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

General Information of Drug (ID: DR0733)
Drug Name
Flutamide
Prodrug Info Flutamide is the prodrug of Flutamide Metabolite M1
Synonyms
Flutamida; Flutamida [INN-Spanish]; Flutamide (Eulexin); Flutamide USP25; Flutamide(Eulexin); Flutamidum; Flutamidum [INN-Latin]; Flutamin; Ham's F-12 medium; Niftholide; Niftolide; Sch 13521; Sch-13521; flutamide; niftolid; Cebatrol, veterinary; Drogenil; Eulexin; 13311-84-7; 2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide; 4'-Nitro-3'-trifluoromethylisobutyranilide; CCRIS 7246; NFBA; NSC 215876; Propanamide, 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-
Indication Prostate cancer [ICD11: 2C82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 276.21 Topological Polar Surface Area 74.9
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
3397
PubChem SID
9855 ; 128648 ; 430151 ; 3221869 ; 5373985 ; 5766070 ; 7847652 ; 8149685 ; 8152166 ; 10321328 ; 11111202 ; 11111203 ; 11335634 ; 11360873 ; 11364104 ; 11366666 ; 11369228 ; 11372441 ; 11374516 ; 11377390 ; 11461845 ; 11466208 ; 11467328 ; 11484718 ; 11485736 ; 11489017 ; 11491236 ; 11492644 ; 11495024 ; 11528366 ; 11532925 ; 11533484 ; 12013361 ; 12146082 ; 15222063 ; 17388997 ; 17405119 ; 24278446 ; 26612139 ; 26679948 ; 26747365 ; 26747366 ; 26753014 ; 26753015 ; 29222532 ; 46508874 ; 47365133 ; 47515269 ; 47515270 ; 47959685
ChEBI ID
ChEBI:5132
CAS Number
13311-84-7
TTD Drug ID
D0Y0SW
Formula
C11H11F3N2O3
Canonical SMILES
CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F
InChI
1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
InChIKey
MKXKFYHWDHIYRV-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
Flutamide Metabolite M1 DM004700
91649
Oxidation - Hydrolyzationn 1 [6]
Flutamide Metabolite M1 DM004700
91649
Unclear 1 [2]
Flutamide Metabolite M2 DM004703
70367046
Unclear 1 [2]
Flutamide Metabolite M3 DM004696
94955
Unclear 1 [2]
Flutamide Metabolite M9 DM004692 N. A. Unclear 1 [2]
Flutamide Metabolite M10 DM004693 N. A. Unclear 2 [2]
Flutamide Metabolite M4 DM004699
246769
Unclear 2 [2]
Flutamide Metabolite M5 DM004697
156595054
Unclear 2 [2]
Flutamide Metabolite M7 DM004701
72355881
Unclear 2 [2]
Flutamide Metabolite M11 DM004694 N. A. Unclear 3 [2]
Flutamide Metabolite M6 DM004698
156596446
Conjugation - Sulfation 3 [2]
Flutamide Metabolite M12 DM004695 N. A. Unclear 4 [2]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005045 Flutamide Flutamide Metabolite M9 Unclear Unclear [2]
MR005049 Flutamide Flutamide Metabolite M3 Unclear AMS [2]
MR005053 Flutamide Flutamide Metabolite M1 Unclear Unclear [2]
MR005055 Flutamide Flutamide Metabolite M2 Unclear Unclear [2]
MR005054 Flutamide Metabolite M1 Flutamide Metabolite M7 Unclear Unclear [2]
MR005050 Flutamide Metabolite M3 Flutamide Metabolite M5 Unclear CYP3A4 [2]
MR005052 Flutamide Metabolite M3 Flutamide Metabolite M4 Unclear Unclear [2]
MR005046 Flutamide Metabolite M9 Flutamide Metabolite M10 Unclear Unclear [2]
MR005047 Flutamide Metabolite M10 Flutamide Metabolite M11 Unclear Unclear [2]
MR005051 Flutamide Metabolite M5 Flutamide Metabolite M6 Conjugation - Sulfation Unclear [2]
MR005048 Flutamide Metabolite M11 Flutamide Metabolite M12 Unclear Unclear [2]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Amylosucrase (AMS) DME1166 Deinococcus geothermalis
Q1J0W0_DEIGD
2.4.1.4
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
⏷ Show the Full List of 7  DME(s)
References
1 Flutamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Transport, metabolism, and hepatotoxicity of flutamide, drug-drug interaction with acetaminophen involving phase I and phase II metabolites
3 Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41.
4 Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1298-303.
5 Identification of a novel glutathione conjugate of flutamide in incubations with human liver microsomes. Drug Metab Dispos. 2007 Jul;35(7):1081-8.
6 DrugBank(Pharmacology-Metabolism):Flutamide

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