Editing Finasteride (section)

{{Short description|Antiandrogen medication}}
{{Use dmy dates|date=October 2022}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 458461973
| image = Finasteride.svg
| image_class = skin-invert-image
| width = 200
| image2 = Finasteride-from-xtal-3D-bs-17.png
| image_class2 = bg-transparent
| width2 = 250
| alt2 = <!-- Clinical data -->
| pronounce = {{IPAc-en|f|ɪ|ˈ|n|æ|s|t|ə|ˌ|r|aɪ|d|audio=LL-Q1860 (eng)-NaomiAmethyst-finasteride.wav}}<br />{{respell|fi|NA|stə|RYDE}}
| tradename = Proscar, Propecia, Finide, others
| Drugs.com = {{drugs.com|monograph|finasteride}}
| MedlinePlus = a698016
| DailyMedID = Finasteride
| pregnancy_AU = X
| pregnancy_category = 
| routes_of_administration = [[By mouth]], [[topical]]
| class = [[5α-Reductase inhibitor]]
| ATC_prefix = G04
| ATC_suffix = CB01
| ATC_supplemental = {{ATC|D11|AX10}}
| legal_AU = S4
| legal_CA = Rx-only
| legal_UK = POM
| legal_UK_comment = <ref>{{Cite web |date=27 July 2020 |title=Propecia 1 mg Film-Coated Tablets - Summary of Product Characteristics (SmPC) |url=https://www.medicines.org.uk/emc/product/2194/smpc |url-status=live |archive-url=https://web.archive.org/web/20200920055119/https://www.medicines.org.uk/emc/product/2194/smpc |archive-date=20 September 2020 |access-date=29 September 2020 |website=(emc)}}</ref><ref>{{Cite web |date=10 July 2020 |title=Proscar 5mg film-coated Tablets - Summary of Product Characteristics (SmPC) |url=https://www.medicines.org.uk/emc/product/1008/smpc |url-status=live |archive-url=https://web.archive.org/web/20200924060320/https://www.medicines.org.uk/emc/product/1008/smpc |archive-date=24 September 2020 |access-date=29 September 2020 |website=(emc)}}</ref>
| legal_US = Rx-only
| legal_US_comment = <ref name="Proscar FDA label">{{Cite web |date=15 November 2019 |title=Proscar- finasteride tablet, film coated |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7c01f541-1c88-400c-41a9-7cbb9dee50c0 |url-status=live |archive-url=https://web.archive.org/web/20210426231856/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7c01f541-1c88-400c-41a9-7cbb9dee50c0 |archive-date=26 April 2021 |access-date=16 September 2020 |website=DailyMed}}</ref><ref name="Propecia FDA label" />

<!-- Pharmacokinetic data -->| bioavailability = 65%<ref name="LemkeWilliams2008">{{Cite book |url=https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA1286 |title=Foye's Principles of Medicinal Chemistry |vauthors=Lemke TL, Williams DA |publisher=Lippincott Williams & Wilkins |year=2008 |isbn=978-0-7817-6879-5 |edition=6th |pages=1286– |access-date=4 December 2017 |archive-url=https://web.archive.org/web/20230110031700/https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA1286 |archive-date=10 January 2023 |url-status=live}}</ref>
| protein_bound = 90%<ref name="LemkeWilliams2008" />
| metabolism = [[Liver]] ([[CYP3A4]], [[aldehyde dehydrogenase|ALDH]])<ref name="LemkeWilliams2008" />
| elimination_half-life = Adults: 5–6 hours<ref name="LemkeWilliams2008" /><br />Elderly: >8 hours<ref name="LemkeWilliams2008" />
| excretion = [[Feces]]: 57%<ref name="LemkeWilliams2008" /><br />[[Urine]]: 40%<ref name="LemkeWilliams2008" />

<!-- Identifiers -->| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 98319-26-7
| PubChem = 57363
| IUPHAR_ligand = 6818
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01216
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 51714
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 57GNO57U7G
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00321
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 5062
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 710
| synonyms = MK-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
<!-- Chemical data -->| IUPAC_name = (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
| C = 23
| H = 36
| N = 2
| O = 2
| SMILES = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DBEPLOCGEIEOCV-WSBQPABSSA-N
}}

<!-- Definition and medical uses -->
'''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.<ref name="AHFS2019">{{Cite web |title=Finasteride Monograph for Professionals |url=https://www.drugs.com/monograph/finasteride.html |url-status=live |archive-url=https://web.archive.org/web/20180825002456/https://www.drugs.com/monograph/finasteride.html |archive-date=25 August 2018 |access-date=5 March 2019 |website=Drugs.com |publisher=American Society of Health-System Pharmacists}}</ref> It can also be used to treat [[hirsutism|excessive hair growth]] in women<ref name="Blume-PeytaviWhiting2008">{{Cite book |url=https://books.google.com/books?id=pHrX2-huQCoC&pg=PA369 |title=Hair Growth and Disorders |vauthors=Blume-Peytavi U, Whiting DA, Trüeb RM |date=26 June 2008 |publisher=Springer Science & Business Media |isbn=978-3-540-46911-7 |pages=369 |access-date=10 December 2016 |archive-url=https://web.archive.org/web/20230110031700/https://books.google.com/books?id=pHrX2-huQCoC&pg=PA369 |archive-date=10 January 2023 |url-status=live}}</ref> It is usually taken [[oral administration|orally]] but there are [[Topical medication|topical formulations]] for patients with hair loss, designed to minimize systemic exposure by acting specifically on hair follicles.<ref name=":0">{{Cite journal |display-authors=6 |vauthors=Piraccini BM, Blume-Peytavi U, Scarci F, Jansat JM, Falqués M, Otero R, Tamarit ML, Galván J, Tebbs V, Massana E |date=February 2022 |title=Efficacy and safety of topical finasteride spray solution for male androgenetic alopecia: a phase III, randomized, controlled clinical trial |journal=Journal of the European Academy of Dermatology and Venereology |volume=36 |issue=2 |pages=286–294 |doi=10.1111/jdv.17738 |pmc=9297965 |pmid=34634163}}</ref>

Finasteride is a [[5α-reductase inhibitor]] and therefore an [[antiandrogen]].<ref>{{Cite book |url=https://books.google.com/books?id=icTsAwAAQBAJ&pg=PA580 |title=Ferri's Clinical Advisor 2015 E-Book: 5 Books in 1 |vauthors=Ferri FF |date=2014 |publisher=Elsevier Health Sciences |isbn=9780323084307 |page=580 |access-date=7 May 2020 |archive-url=https://web.archive.org/web/20230110031742/https://books.google.com/books?id=icTsAwAAQBAJ&pg=PA580 |archive-date=10 January 2023 |url-status=live}}</ref> It works by [[enzyme inhibitor|decreasing]] the [[biosynthesis|production]] of [[dihydrotestosterone]] (DHT) by about 70%.<ref name=AHFS2019/>

In addition to DHT, finasteride also inhibits the production of several anticonvulsant neurosteroids including [[allopregnanolone]], [[androstanediol]], and [[tetrahydrodeoxycorticosterone]].<ref>{{Cite journal |vauthors=Samba Reddy D, Ramanathan G |date=September 2012 |title=Finasteride inhibits the disease-modifying activity of progesterone in the hippocampus kindling model of epileptogenesis |journal=Epilepsy & Behavior |volume=25 |issue=1 |pages=92–7 |doi=10.1016/j.yebeh.2012.05.024 |pmc=3444667 |pmid=22835430}}</ref>

<!--Adverse effects and mechanism -->
[[Adverse effects]] from finasteride are rare in men with already enlarged prostates;<ref name="Cochrane2010">{{Cite journal |vauthors=Tacklind J, Fink HA, Macdonald R, Rutks I, Wilt TJ |date=October 2010 |title=Finasteride for benign prostatic hyperplasia |journal=The Cochrane Database of Systematic Reviews |volume=2015 |issue=10 |pages=CD006015 |doi=10.1002/14651858.CD006015.pub3 |pmc=8908761 |pmid=20927745}}</ref> however, some men experience [[sexual dysfunction]], [[depression (mood)|depression]], and [[gynecomastia|breast enlargement]].<ref name="Zak2019">{{Cite journal |vauthors=Zakhem GA, Goldberg JE, Motosko CC, Cohen BE, Ho RS |date=July 2019 |title=Sexual dysfunction in men taking systemic dermatologic medication: A systematic review |journal=Journal of the American Academy of Dermatology |volume=81 |issue=1 |pages=163–172 |doi=10.1016/j.jaad.2019.03.043 |pmid=30905792 |s2cid=85497115}}</ref><ref name="2014AArev">{{Cite journal |vauthors=Varothai S, Bergfeld WF |date=July 2014 |title=Androgenetic alopecia: an evidence-based treatment update |journal=American Journal of Clinical Dermatology |volume=15 |issue=3 |pages=217–30 |doi=10.1007/s40257-014-0077-5 |pmid=24848508 |s2cid=31245042}}</ref> In some men, sexual dysfunction may persist after stopping the medication.<ref name="Zax2019">{{Cite journal |vauthors=Zakhem GA, Goldberg JE, Motosko CC, Cohen BE, Ho RS |date=July 2019 |title=Sexual dysfunction in men taking systemic dermatologic medication: A systematic review |journal=Journal of the American Academy of Dermatology |volume=81 |issue=1 |pages=163–172 |doi=10.1016/j.jaad.2019.03.043 |pmid=30905792 |s2cid=85497115 |quote=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.}}</ref><ref name="Tra2020">{{Cite journal |vauthors=Traish AM |date=January 2020 |title=Post-finasteride syndrome: a surmountable challenge for clinicians |journal=Fertility and Sterility |volume=113 |issue=1 |pages=21–50 |doi=10.1016/j.fertnstert.2019.11.030 |pmid=32033719 |s2cid=211064052 |doi-access=free}}</ref> It may also hide the early symptoms of certain forms of [[prostate cancer]].<ref name=2014AArev/>

<!-- History, society, and culture -->
Finasteride was patented in 1984 and approved for medical use in 1992.<ref name="Fis2006">{{Cite book |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA483 |title=Analogue-based Drug Discovery |vauthors=Fischer J, Ganellin CR |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=483 |access-date=7 May 2020 |archive-url=https://web.archive.org/web/20230110031701/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA483 |archive-date=10 January 2023 |url-status=live}}</ref> It is available as a [[generic medication]].<ref name="SataloffSclafani2015">{{Cite book |url=https://books.google.com/books?id=acswCwAAQBAJ&pg=PA400 |title=Sataloff's Comprehensive Textbook of Otolaryngology: Head & Neck Surgery: Facial Plastic and Reconstructive Surgery |vauthors=Sataloff RT, Sclafani AP |date=30 November 2015 |publisher=JP Medical Ltd |isbn=978-93-5152-459-5 |pages=400– |access-date=4 December 2017 |archive-url=https://web.archive.org/web/20230110031702/https://books.google.com/books?id=acswCwAAQBAJ&pg=PA400 |archive-date=10 January 2023 |url-status=live}}</ref> In 2022, it was the 73rd most commonly prescribed medication in the United States, with more than 9{{nbsp}}million prescriptions.<ref>{{Cite web |title=The Top 300 of 2022 |url=https://clincalc.com/DrugStats/Top300Drugs.aspx |url-status=live |archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx |archive-date=30 August 2024 |access-date=30 August 2024 |website=ClinCalc}}</ref><ref>{{Cite web |title=Finasteride Drug Usage Statistics, United States, 2013–2022 |url=https://clincalc.com/DrugStats/Drugs/Finasteride |access-date=30 August 2024 |website=ClinCalc}}</ref>
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