Finasteride

Finasteride
Clinical data
Trade namesProscar, Propecia, Finide, others
Other namesMK-906; YM-152; L-652,931; 17β-(N-tert-Butylcarbamoyl)-4-aza-5α-androst-1-en-3-one; N-(1,1-Dimethylethyl)-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
AHFS/Drugs.comMonograph
MedlinePlusa698016
License data
Pregnancy
category
  • AU: X (High risk)
Routes of
administration		By mouth
Drug class5α-Reductase inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability65%[5]
Protein binding90%[5]
MetabolismLiver (CYP3A4, ALDH)[5]
Elimination half-lifeAdults: 5–6 hours[5]
Elderly: >8 hours[5]
ExcretionFeces: 57%[5]
Urine: 40%[5]
Identifiers
  • (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-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 InfoCard100.149.445 Edit this at Wikidata
Chemical and physical data
FormulaC23H36N2O2
Molar mass372.553 g·mol−1
3D model (JSmol)
  • O=C(NC(C)(C)C)[C@@H]2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4NC(=O)\C=C/[C@]34C)C
  • InChI=1S/C23H36N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h11,13-18H,6-10,12H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1 checkY
  • Key:DBEPLOCGEIEOCV-WSBQPABSSA-N checkY
  (verify)

Finasteride, sold under the brand names Proscar and Propecia among others, is a medication used to treat pattern hair loss and benign prostatic hyperplasia (BPH) in men.[6] It can also be used to treat excessive hair growth in women.[7][8] It is usually taken orally but there are topical formulations for patients with hair loss, designed to minimize systemic exposure by acting specifically on hair follicles.[9]

Finasteride is a 5α-reductase inhibitor and therefore an antiandrogen.[10] It works by decreasing the production of dihydrotestosterone (DHT) by about 70%.[6]

In addition to DHT, finasteride also inhibits the production of several anticonvulsant neurosteroids including allopregnanolone, androstanediol, and tetrahydrodeoxycorticosterone.[11]

Adverse effects from finasteride are rare in men with already enlarged prostates;[12] however, some men experience sexual dysfunction, depression, and breast enlargement.[13][14] In some men, sexual dysfunction may persist after stopping the medication.[15][16] It may also hide the early symptoms of certain forms of prostate cancer.[14]

Finasteride was patented in 1984 and approved for medical use in 1992.[17] It is available as a generic medication.[18] In 2022, it was the 73rd most commonly prescribed medication in the United States, with more than 9 million prescriptions.[19][20]

  1. ^ "Propecia 1 mg Film-Coated Tablets - Summary of Product Characteristics (SmPC)". (emc). 27 July 2020. Archived from the original on 20 September 2020. Retrieved 29 September 2020.
  2. ^ "Proscar 5mg film-coated Tablets - Summary of Product Characteristics (SmPC)". (emc). 10 July 2020. Archived from the original on 24 September 2020. Retrieved 29 September 2020.
  3. ^ "Proscar- finasteride tablet, film coated". DailyMed. 15 November 2019. Archived from the original on 26 April 2021. Retrieved 16 September 2020.
  4. ^ Cite error: The named reference Propecia FDA label was invoked but never defined (see the help page).
  5. ^ a b c d e f g Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry (6th ed.). Lippincott Williams & Wilkins. pp. 1286–. ISBN 978-0-7817-6879-5. Archived from the original on 10 January 2023. Retrieved 4 December 2017.
  6. ^ a b "Finasteride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 25 August 2018. Retrieved 5 March 2019.
  7. ^ Blume-Peytavi U, Whiting DA, Trüeb RM (26 June 2008). Hair Growth and Disorders. Springer Science & Business Media. p. 369. ISBN 978-3-540-46911-7. Archived from the original on 10 January 2023. Retrieved 10 December 2016.
  8. ^ Knezevich EL, Viereck LK, Drincic AT (January 2012). "Medical management of adult transsexual persons". Pharmacotherapy. 32 (1): 54–66. doi:10.1002/PHAR.1006. PMID 22392828. S2CID 12853220.
  9. ^ Piraccini BM, Blume-Peytavi U, Scarci F, Jansat JM, Falqués M, Otero R, et al. (February 2022). "Efficacy and safety of topical finasteride spray solution for male androgenetic alopecia: a phase III, randomized, controlled clinical trial". Journal of the European Academy of Dermatology and Venereology. 36 (2): 286–294. doi:10.1111/jdv.17738. PMC 9297965. PMID 34634163.
  10. ^ Ferri FF (2014). Ferri's Clinical Advisor 2015 E-Book: 5 Books in 1. Elsevier Health Sciences. p. 580. ISBN 9780323084307. Archived from the original on 10 January 2023. Retrieved 7 May 2020.
  11. ^ Samba Reddy D, Ramanathan G (September 2012). "Finasteride inhibits the disease-modifying activity of progesterone in the hippocampus kindling model of epileptogenesis". Epilepsy & Behavior. 25 (1): 92–7. doi:10.1016/j.yebeh.2012.05.024. PMC 3444667. PMID 22835430.
  12. ^ Tacklind J, Fink HA, Macdonald R, Rutks I, Wilt TJ (October 2010). "Finasteride for benign prostatic hyperplasia". The Cochrane Database of Systematic Reviews. 2015 (10): CD006015. doi:10.1002/14651858.CD006015.pub3. PMC 8908761. PMID 20927745.
  13. ^ Zakhem GA, Goldberg JE, Motosko CC, Cohen BE, Ho RS (July 2019). "Sexual dysfunction in men taking systemic dermatologic medication: A systematic review". Journal of the American Academy of Dermatology. 81 (1): 163–172. doi:10.1016/j.jaad.2019.03.043. PMID 30905792. S2CID 85497115.
  14. ^ a b Varothai S, Bergfeld WF (July 2014). "Androgenetic alopecia: an evidence-based treatment update". American Journal of Clinical Dermatology. 15 (3): 217–30. doi:10.1007/s40257-014-0077-5. PMID 24848508. S2CID 31245042.
  15. ^ Zakhem GA, Goldberg JE, Motosko CC, Cohen BE, Ho RS (July 2019). "Sexual dysfunction in men taking systemic dermatologic medication: A systematic review". Journal of the American Academy of Dermatology. 81 (1): 163–172. doi:10.1016/j.jaad.2019.03.043. PMID 30905792. S2CID 85497115. In studies addressing reversibility, most of these patients have resolution of sexual adverse effects after discontinuation of finasteride, and many have improvement of adverse effects over time with continued finasteride use. However, some studies describe a subset of patients with persistent adverse effects after discontinuation... Level 1 evidence evaluating sexual dysfunction as a primary outcome was available for finasteride.
  16. ^ Traish AM (January 2020). "Post-finasteride syndrome: a surmountable challenge for clinicians". Fertility and Sterility. 113 (1): 21–50. doi:10.1016/j.fertnstert.2019.11.030. PMID 32033719. S2CID 211064052.
  17. ^ 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 7 May 2020.
  18. ^ Sataloff RT, Sclafani AP (30 November 2015). Sataloff's Comprehensive Textbook of Otolaryngology: Head & Neck Surgery: Facial Plastic and Reconstructive Surgery. JP Medical Ltd. pp. 400–. ISBN 978-93-5152-459-5. Archived from the original on 10 January 2023. Retrieved 4 December 2017.
  19. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  20. ^ "Finasteride Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.