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

General Information of Drug (ID: DR0210)
Drug Name
Bicalutamide
Synonyms
Bicalutamide (CDX); Bicalutamide (Casodex); Bicalutamide(Casodex); Calutide; Casodex; Cosudex; Kalumid; LKJPYSCBVHEWIU-UHFFFAOYSA-N; bicalutamide; (+-)-4'-Cyano-alpha,alpha,alpha-trifluoro-3-((p-fluorophenyl)sulfonyl)-2-methyl-m-lactotoluidide; 90357-06-5; BRN 5364666; C18H14F4N2O4S; CHEMBL409; ICI 176334; ICI-176334; MFCD00869971; N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide; N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methylpropanamide
Indication Prostate cancer [ICD11: 2C82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 430.4 Topological Polar Surface Area 116
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
2375
PubChem SID
10360 ; 536636 ; 4422035 ; 7848024 ; 7978493 ; 8151593 ; 11528703 ; 12014029 ; 14807515 ; 26719836 ; 29221542 ; 46386630 ; 46505386 ; 46518598 ; 49681685 ; 49835627 ; 50113021 ; 50709017 ; 53790604 ; 57321290 ; 85174226 ; 85174230 ; 90341766 ; 91610973 ; 92308263 ; 92308948 ; 92711409 ; 93815120 ; 99016301 ; 99437214 ; 103164349 ; 104300407 ; 118046574 ; 121362017 ; 124658945 ; 124757067 ; 124800143 ; 124893438 ; 125163871 ; 125338410 ; 125359510 ; 125545351 ; 126630887 ; 126657361 ; 126665838 ; 128501765 ; 131295154 ; 134358448 ; 135014383 ; 135649993
ChEBI ID
ChEBI:3090
CAS Number
90357-06-5
TTD Drug ID
D0V9BD
Formula
C18H14F4N2O4S
Canonical SMILES
CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
InChI
1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
InChIKey
LKJPYSCBVHEWIU-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
Hydroxy(R)bicalutamide DM001418 N. A. Oxidation - Hydroxylation 1 [5]
S-bicalutamide-glucuronide DM001420 N. A. Unclear 1 [3] , [5]
R-bicalutamide-glucuronide DM001419 N. A. Unclear 2 [3] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000363 Bicalutamide Hydroxy(R)bicalutamide Oxidation - Hydroxylation Unclear [5]
MR000364 Bicalutamide S-bicalutamide-glucuronide Unclear UGT1A8 ... [3], [5]
MR000362 Hydroxy(R)bicalutamide R-bicalutamide-glucuronide Unclear UGT1A9 ... [3], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
References
1 Bicalutamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78.
3 Enantiomer selective glucuronidation of the non-steroidal pure anti-androgen bicalutamide by human liver and kidney: role of the human UDP-glucuronosyltransferase (UGT)1A9 enzyme Basic Clin Pharmacol Toxicol. 2013 Aug;113(2):92-102. doi: 10.1111/bcpt.12071.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Dailymed:Bicalutamide

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