dutasteride   

GtoPdb Ligand ID: 7457

Synonyms: Avodart® | GG-745 | GI-198745
dutasteride is an approved drug (FDA (2001))
Comment: Dutasteride is a 5α-reductase inhibitor, which inhibits conversion of testosterone to dihydrotestosterone (DHT). There are three 5α-reductase isozymes: SRD5A1, SRD5A2 and SRD5A3, all of which are inhibited by dutasteride [1-2].
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: dutasteride

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 58.2
Molecular weight 528.22
XLogP 6.77
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C1C=CC2(C(N1)CCC1C2CCC2(C1CCC2C(=O)Nc1cc(ccc1C(F)(F)F)C(F)(F)F)C)C
Isomeric SMILES O=C1C=C[C@]2([C@H](N1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)Nc1cc(ccc1C(F)(F)F)C(F)(F)F)C)C
InChI 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
InChI Key JWJOTENAMICLJG-QWBYCMEYSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (2001))
IUPAC Name
(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
International Nonproprietary Names
INN number INN
7586 dutasteride
Synonyms
Avodart® | GG-745 | GI-198745
Database Links
CAS Registry No. 164656-23-9
ChEBI CHEBI:521033
ChEMBL Ligand CHEMBL1200969
DrugBank Ligand DB01126
DrugCentral Ligand 973
GtoPdb PubChem SID 187051760
PubChem CID 6918296
Search Google for chemical match using the InChIKey JWJOTENAMICLJG-QWBYCMEYSA-N
Search Google for chemicals with the same backbone JWJOTENAMICLJG
Search PubMed clinical trials dutasteride
Search PubMed titles dutasteride
Search PubMed titles/abstracts dutasteride
Search UniChem for chemical match using the InChIKey JWJOTENAMICLJG-QWBYCMEYSA-N
Search UniChem for chemicals with the same backbone JWJOTENAMICLJG
Wikipedia Dutasteride