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

General Information of Drug (ID: DR0555)
Drug Name
Dutasteride
Synonyms
Dutasteride; Dutasteride, 99%; GG 745; GG-745; GI 198745; GI-198745; GI198745; Avodart; Avolve; O0J6XJN02I; (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide; (5alpha,17beta)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide; 164656-23-9; CHEBI:521033; CHEMBL1200969; UNII-O0J6XJN02I
Indication Prostatic hyperplasia [ICD11: GA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 528.5 Topological Polar Surface Area 58.2
Heavy Atom Count 37 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
6918296
PubChem SID
12014955 ; 14836607 ; 14909902 ; 17194796 ; 17397907 ; 43529678 ; 46504830 ; 53787436 ; 57371871 ; 71824992 ; 79317270 ; 81092907 ; 85709776 ; 91145910 ; 91612910 ; 99437024 ; 103770952 ; 104179082 ; 114787740 ; 118046363 ; 124757077 ; 125163881 ; 125311722 ; 126596711 ; 131343417 ; 135109202 ; 135684130 ; 136183917 ; 136367959 ; 136375517 ; 136980377 ; 137005555 ; 137181708 ; 142643797 ; 144115926 ; 144205752 ; 152059555 ; 152063850 ; 162036214 ; 162175331 ; 163797282 ; 165698504 ; 172093501 ; 174477509 ; 174527666 ; 175265390 ; 176484953 ; 179150039 ; 187051760 ; 210274902
ChEBI ID
CHEBI:521033
CAS Number
164656-23-9
TTD Drug ID
D0A9YA
Formula
C27H30F6N2O2
Canonical SMILES
CC12CCC3C(C1CCC2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CCC5C3(C=CC(=O)N5)C
InChI
1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1
InChIKey
JWJOTENAMICLJG-QWBYCMEYSA-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
1,2-dihydrodutasteride DM005432
15871205
Oxidation - Hydrolyzationn 1 [3]
4'-hydroxydutasteride DM005430
125407586
Oxidation - Hydrolyzationn 1 [3]
6beta-hydroxydutasteride DM005431 N. A. Oxidation - Hydrolyzationn 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005771 Dutasteride 4'-hydroxydutasteride Oxidation - Hydrolyzationn CYP3A4 ... [3]
MR005772 Dutasteride 6beta-hydroxydutasteride Oxidation - Hydrolyzationn CYP3A4 ... [3]
MR005773 Dutasteride 1,2-dihydrodutasteride Oxidation - Hydrolyzationn CYP3A4 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
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
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
References
1 Dutasteride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Duloxetine: clinical pharmacokinetics and drug interactions. Clin Pharmacokinet. 2011 May;50(5):281-94.
3 LC-MS/MS determination of dutasteride and its major metabolites in human plasma
4 Drug interactions between common dermatological medications and the oral anti-COVID-19 agents nirmatrelvir-ritonavir and molnupiravir
5 Product monograph: Avodart (dutasteride capsules).
6 DrugBank(Pharmacology-Metabolism):Dutasteride

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