Dutasteride

Dutasteride
Clinical data
Pronunciation/duˈtæstəˌraɪd/
doo-TA-stə-RYDE
Trade namesAvodart, others
Other namesGG-745; GI-198745; GI-198745X; N-[2,5-Bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
AHFS/Drugs.comMonograph
MedlinePlusa603001
License data
Pregnancy
category
  • Not to be used during pregnancy
Routes of
administration		By mouth
Drug class5α-Reductase inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60%[1]
Protein binding99%[1]
MetabolismLiver (CYP3A4)[1]
Metabolites• 4'-Hydroxydutasteride[1]
• 6'-Hydroxydutasteride[1]
• 1,2-Dihydrodutasteride[1]
(All three active)[1]
Elimination half-life4–5 weeks[2][3]
ExcretionFeces: 40% (metabolites)[1]
Urine: 5% (unchanged)[1]
Identifiers
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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.166.372
Chemical and physical data
FormulaC27H30F6N2O2
Molar mass528.539 g·mol−1
3D model (JSmol)
Density1.346 g/cm3 at 294 K (calculated) [4]
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
  (verify)

Dutasteride, sold under the brand name Avodart among others, is a medication primarily used to treat the symptoms of a benign prostatic hyperplasia (BPH), an enlarged prostate not associated with cancer. A few months may be required before benefits occur.[5] It is also used for scalp hair loss in men and as a part of hormone therapy in transgender women.[6][7] It is usually taken by mouth.[8][9][5]

The most commonly reported side effects of dutasteride, although rare, include sexual dysfunction and depression.[10] In the largest available study of 6,729 men with BPH, 9% experienced erectile dysfunction (compared to 5.7% treated with a placebo), 3.3% experienced decreased sex drive (vs 1.6% of placebo), and 1.9% had enlarged breasts (vs 1% of placebo).[11][12] Exposure during pregnancy is specifically contraindicated because antiandrogens such as dutasteride have been shown to interfere with the sexual development of male fetuses.[3][8]

Dutasteride was patented in 1993 by Glaxo Wellcome (later known as GSK after additional mergers) and was approved for medical use in 2001.[13][8] In the United States and elsewhere, it is available as a generic medication.[5] In 2018, it was the 291st-most commonly prescribed medication in the US with more than 1 million prescriptions.[14]

  1. ^ a b c d e f g h i Cite error: The named reference LemkeWilliams2008 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference BurchumRosenthal2014 was invoked but never defined (see the help page).
  3. ^ a b Blume-Peytavi U, Whiting DA, Trüeb RM (26 June 2008). Hair Growth and Disorders. Springer Science & Business Media. pp. 182, 369. ISBN 978-3-540-46911-7. Archived from the original on 10 January 2023. Retrieved 10 December 2016.
  4. ^ https://pubs.rsc.org/en/content/getauthorversionpdf/C5CE00036J
  5. ^ a b c British National Formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 769. ISBN 9780857113382.
  6. ^ Shapiro J, Otberg N (17 April 2015). Hair Loss and Restoration, Second Edition. CRC Press. pp. 39–. ISBN 978-1-4822-3199-1. Archived from the original on 12 January 2023. Retrieved 27 October 2016.
  7. ^ Wesp LM, Deutsch MB (March 2017). "Hormonal and Surgical Treatment Options for Transgender Women and Transfeminine Spectrum Persons". The Psychiatric Clinics of North America. 40 (1): 99–111. doi:10.1016/j.psc.2016.10.006. PMID 28159148.
  8. ^ a b c "Dutasteride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 4 July 2019. Retrieved 18 March 2019.
  9. ^ Wu C, Kapoor A (July 2013). "Dutasteride for the treatment of benign prostatic hyperplasia". Expert Opinion on Pharmacotherapy. 14 (10): 1399–1408. doi:10.1517/14656566.2013.797965. PMID 23750593. S2CID 25041466.
  10. ^ Cite error: The named reference Traish2015 was invoked but never defined (see the help page).
  11. ^ Fertig RM, Gamret AC, Darwin E, Gaudi S (November 2017). "Sexual side effects of 5-α-reductase inhibitors finasteride and dutasteride: A comprehensive review". Dermatology Online Journal. 23 (11). doi:10.5070/D32311037240. PMID 29447628.
  12. ^ Andriole GL, Bostwick DG, Brawley OW, Gomella LG, Marberger M, Montorsi F, et al. (April 2010). "Effect of dutasteride on the risk of prostate cancer". The New England Journal of Medicine. 362 (13): 1192–1202. doi:10.1056/NEJMoa0908127. PMID 20357281.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 483. ISBN 9783527607495. Archived from the original on 10 January 2023. Retrieved 19 September 2020.
  14. ^ "Dutasteride – Drug Usage Statistics". ClinCalc. Archived from the original on 6 February 2020. Retrieved 7 October 2022.
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