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

General Information of Drug (ID: DR1158)
Drug Name
Nilutamide
Synonyms
Nilandron; Nilandrone; Nilutamida; Nilutamida [Spanish]; Nilutamide [USAN:INN:BAN]; Nilutamidum; Nilutamidum [Latin]; RU 23908; Anandron; RU 23908-10; RU-23908; XWXYUMMDTVBTOU-UHFFFAOYSA-N; nilutamide; 5,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin; 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)imidazolidine-2,4-dione; 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione; 63612-50-0; BRN 0841906; C12H10F3N3O4; CHEBI:7573; CHEMBL1274; UNII-51G6I8B902
Indication Prostate cancer [ICD11: 2C82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 317.22 Topological Polar Surface Area 95.2
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
4493
PubChem SID
10364 ; 5851647 ; 7404097 ; 7848028 ; 7978498 ; 8152766 ; 11111555 ; 11111556 ; 11114201 ; 11342173 ; 11362356 ; 11364519 ; 11367081 ; 11369643 ; 11372644 ; 11374239 ; 11377805 ; 11466956 ; 11468076 ; 11485861 ; 11486751 ; 11487758 ; 11489789 ; 11491448 ; 11492415 ; 11495439 ; 12013485 ; 14850346 ; 17405438 ; 24278596 ; 26612639 ; 26680190 ; 26747174 ; 26747175 ; 26752242 ; 29223587 ; 46505381 ; 47365306 ; 47365307 ; 47959867 ; 48110544 ; 48259346 ; 48259347 ; 48334600 ; 49698835 ; 49980214 ; 50104947 ; 50104948 ; 50104949 ; 50104950
ChEBI ID
ChEBI:7573
CAS Number
63612-50-0
TTD Drug ID
D0SN9T
Formula
C12H10F3N3O4
Canonical SMILES
CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C
InChI
1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)
InChIKey
XWXYUMMDTVBTOU-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
Nilutamide metabolite M2 DM002203
141744293
Unclear 1 [4]
Nilutamide metabolite M6 DM002209 N. A. Unclear 1 [4]
Nilutamide metabolite M8 DM002208
14405755
Unclear 1 [4]
Nilutamide metabolite M3 DM002204
15838442
Unclear 2 [4]
Nilutamide metabolite M4 DM002205 N. A. Unclear 3 [4]
Nilutamide metabolite M7 DM002206 N. A. Unclear 3 [4]
Nilutamide metabolite M9 DM002207
16770402
Unclear 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003277 Nilutamide Nilutamide metabolite M2 Unclear Unclear [4]
MR003278 Nilutamide Nilutamide metabolite M8 Unclear Unclear [4]
MR003279 Nilutamide Nilutamide metabolite M6 Unclear Unclear [4]
MR003273 Nilutamide metabolite M2 Nilutamide metabolite M3 Unclear Unclear [4]
MR003274 Nilutamide metabolite M3 Nilutamide metabolite M4 Unclear Unclear [4]
MR003275 Nilutamide metabolite M3 Nilutamide metabolite M7 Unclear Unclear [4]
MR003276 Nilutamide metabolite M3 Nilutamide metabolite M9 Unclear Unclear [4]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
NADPH-cytochrome P450 reductase (CPR) DME0076 Homo sapiens
NCPR_HUMAN
1.6.2.4
[3]
References
1 Nilutamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Nilutamide inhibits mephenytoin 4-hydroxylation in untreated male rats and in human liver microsomes. Xenobiotica. 1991 Dec;21(12):1559-70.
3 Generation of free radicals during the reductive metabolism of nilutamide by lung microsomes: possible role in the development of lung lesions in patients treated with this anti-androgen. Biochem Pharmacol. 1992 Feb 4;43(3):654-7.
4 Pharmacokinetics and metabolism of nilutamide Urology. 1991;37(2 Suppl):13-9. doi: 10.1016/0090-4295(91)80096-p.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.