Drug nameDutasteride
DescriptionDutasteride belongs to a class of drugs called 5-alpha-reductase inhibitors, which block the action of the 5-alpha-reductase enzymes that convert testosterone into dihydrotestosterone (DHT). Finasteride also belongs to this group. Dutasteride inhibits both isoforms of 5-alpha reductase, while finasteride inhibits only one. But a clinical study done by GlaxoSmithKline, the EPICS trial, did not find dutasteride to be more effective than finasteride in treating BPH. [Wikipedia]
DrugBankPrimary Accession Number: DB01126
DIN02247813
TypeApproved, Investigational, Small Molecule
IndicationFor the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate gland.
Mechanism of ActionDutasteride inhibits the conversion of testosterone to 5 alpha-dihydrotestosterone (DHT). DHT is the androgen primarily responsible for the initial development and subsequent enlargement of the prostate gland. Testosterone is converted to DHT by the enzyme 5 alpha-reductase, which exists as 2 isoforms, type 1 and type 2. The type 2 isoenzyme is primarily active in the reproductive tissues while the type 1 isoenzyme is also responsible for testosterone conversion in the skin and liver. Dutasteride is a competitive and specific inhibitor of both type 1 and type 2 5 alpha-reductase isoenzymes, with which it forms a stable enzyme complex. Dissociation from this complex has been evaluated under in vitro and in vivo conditions and is extremely slow. Dutasteride does not bind to the human androgen receptor.
Absorption60%
ToxicityNot available
Protein Binding99%
Interactions
RXListhttp://www.rxlist.com/cgi/generic3/duagen.htm
KEGGdrug: Not available / compound: Not Available
PubChemcompound: 152945 / substance: 730446
PharmGKBPA164749300
Metabolizing Enzymes
NameGeneEntrezIDUniprotSNP
Cytochrome P450 3A4 (CYP3A4)CYP3A41576P08684rs13306281
Target
NameGeneEntrezIDSwissprotSNP
3-oxo-5-alpha-steroid 4-dehydrogenase 1SRD5A16715S5A1_HUMANrs3822430 rs248793 rs10062086 rs8192208 rs8192186 rs3736316 rs523854
3-oxo-5-alpha-steroid 4-dehydrogenase 2SRD5A26716S5A2_HUMANrs523349 rs58432514 rs34552434 rs28383064 rs28383048 rs9332967 rs9332966 rs9332965 rs9332964 rs9332963 rs9332962 rs9332961 rs9332960 rs9282858
FilesDB01126.mol | DB01126_2002-10-01.pdf | pdb_1376850324834-0.pdb | sdf_9325657814996-0.sdf |
Smilesisomeric:
C[C@]12CC[C@H]3[C@@H](CC[C@H]4NC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)NC
1=C(C=CC(=C1)C(F)(F)F)C(F)(F)F
canonical:
CC12CCC3C(CCC4NC(=O)C=CC34C)C1CCC2C(=O)NC1=C(C=CC(=C1)C(F)(F)F)C(F)(F)
F

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