Dutasteride

Dutasteride

Clinical data
Trade names	Avodart
AHFS/Drugs.com	Monograph
MedlinePlus	a603001
Pregnancy category	US: X (Contraindicated) Not to be handled by pregnant women
Routes of administration	By mouth
ATC code	G04CB02 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60%
Protein binding	99%
Metabolism	Liver (CYP3A4-mediated)
Biological half-life	4 to 5 weeks
Excretion	Feces
Identifiers
IUPAC name (5α, 17β)-N-{2,5-Bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide
Synonyms	GG-745, GI-198745
CAS Number	164656-23-9 Y
PubChem (CID)	6918296
IUPHAR/BPS	7457
DrugBank	DB01126 Y
ChemSpider	5293502 Y
UNII	O0J6XJN02I Y
KEGG	D03820 Y
ChEBI	CHEBI:521033 Y
ChEMBL	CHEMBL1200969 N
ECHA InfoCard	100.166.372
Chemical and physical data
Formula	C27H30F6N2O2
Molar mass	528.53 g/mol
3D model (Jmol)	Interactive image
SMILES FC(F)(F)c1cc(c(cc1)C(F)(F)F)NC(=O)[C@@H]3[C@]2(CC[C@H]4[C@H]([C@@H]2CC3)CC[C@H]5NC(=O)\C=C/[C@]45C)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 Y Key:JWJOTENAMICLJG-QWBYCMEYSA-N Y
NY (what is this?)

Dutasteride, sold under the brand name Avodart among others, is a medication used to treat benign prostatic hyperplasia (enlarged prostate) and androgenetic alopecia (pattern hair loss).

It was developed by GlaxoSmithKline and is a 5α-reductase inhibitor which prevents the conversion of the androgen sex hormone testosterone into the more potent dihydrotestosterone (DHT). The drug has been licensed for the treatment of androgenetic alopecia in South Korea since 2009, but has not been approved for this specific indication in the United States, though it is commonly used off-label.

Dutasteride is useful for treating benign prostatic hyperplasia (BPH); colloquially known as an "enlarged prostate". It is approved by the Food and Drug Administration (FDA) in the U.S. for this indication.

In those who are being regularly screened, 5α-reductase inhibitors such as finasteride and dutasteride reduce the overall risk of being diagnosed with prostate cancer; however, there is insufficient data to determine if they have an effect on the risk of death and may increase the chance of more serious cases.

Dutasteride is approved for the treatment of male androgenetic alopecia in South Korea at a dosage of 0.5 mg per day. It has been found in several studies to improve hair growth in men more rapidly and to a greater extent than 2.5 mg/day finasteride. Dutasteride has also been used off-label in the treatment of female pattern hair loss.