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Revision as of 10:40, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{drugbox}} taken from revid 456724777 of page Dutasteride for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').  Latest revision as of 06:29, 14 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{Short description|Hormone replacement medication}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=March 2024}}
{{Drugbox
{{cs1 config |name-list-style=vanc |display-authors=6}}
| Verifiedfields = changed
{{Infobox drug
| verifiedrevid = 400830078
| Verifiedfields = verified
| IUPAC_name = (5α, 17β)-''N''-{2,5 bis(trifluoromethyl) phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide
| Watchedfields = verified
| verifiedrevid = 461091686
| image = Dutasteride.svg | image = Dutasteride.svg
| image_class = skin-invert-image
| width = 217
| width = 250


<!--Clinical data--> <!--Clinical data-->
| tradename = Avodart | tradename = Avodart, others
| Drugs.com = {{drugs.com|monograph|dutasteride}} | Drugs.com = {{drugs.com|monograph|dutasteride}}
| MedlinePlus = a603001 | MedlinePlus = a603001
| DailyMedID = Dutasteride
| pregnancy_US = X
| pregnancy_category = '''Not to be handled by pregnant women''' | pregnancy_category = Not to be used during pregnancy
| routes_of_administration = ]
| class = ]
| ATC_prefix = G04
| ATC_suffix = CB02
| ATC_supplemental =

| legal_UK = POM | legal_UK = POM
| legal_US = Rx-only | legal_US = Rx-only
| routes_of_administration = Oral


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 60% | bioavailability = 60%<ref name="LemkeWilliams2008" />
| protein_bound = 99% | protein_bound = 99%<ref name="LemkeWilliams2008" />
| metabolism = ] (]-mediated) | metabolism = ] (])<ref name="LemkeWilliams2008" />
| metabolites = • 4'-Hydroxydutasteride<ref name="LemkeWilliams2008" /><br />• 6'-Hydroxydutasteride<ref name="LemkeWilliams2008" /><br />• 1,2-Dihydrodutasteride<ref name="LemkeWilliams2008" /><br />(All three active)<ref name="LemkeWilliams2008" />
| elimination_half-life = 5 weeks
| elimination_half-life = 4–5 weeks<ref name="BurchumRosenthal2014" /><ref name="Blu2008" />
| excretion = Fecal
| excretion = ]: 40% (metabolites)<ref name="LemkeWilliams2008" /><br />]: 5% (unchanged)<ref name="LemkeWilliams2008" />


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 164656-23-9 | CAS_number = 164656-23-9
| ATC_prefix = G04
| ATC_suffix = CB02
| ATC_supplemental =
| PubChem = 6918296 | PubChem = 6918296
| IUPHAR_ligand = 7457
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01126 | DrugBank = DB01126
Line 38: Line 44:
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O0J6XJN02I | UNII = O0J6XJN02I
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03820 | KEGG = D03820
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 521033 | ChEBI = 521033
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1200969 --> | ChEMBL = 1200969
| synonyms = GG-745; GI-198745; GI-198745X; ''N''--3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
| C=27 | H=30 | F=6 | N=2 | O=2

| molecular_weight = 528.53 g/mol
<!--Chemical data-->
| smiles = FC(F)(F)c1cc(c(cc1)C(F)(F)F)NC(=O)32(CC4(2CC3)CC5NC(=O)\C=C/45C)C
| IUPAC_name = (1S,3aS,3bS,5aR,9aR,9bS,11aS)-''N''--9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindenoquinoline-1-carboxamide
| InChI = 1/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
| C=27 | H=30 | F=6 | N=2 | O=2
| InChIKey = JWJOTENAMICLJG-QWBYCMEYBZ
| SMILES = FC(F)(F)c1cc(c(cc1)C(F)(F)F)NC(=O)32(CC4(2CC3)CC5NC(=O)\C=C/45C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JWJOTENAMICLJG-QWBYCMEYSA-N | StdInChIKey = JWJOTENAMICLJG-QWBYCMEYSA-N
| density = 1.346
| density_notes= at 294&nbsp;K (calculated) <ref>https://pubs.rsc.org/en/content/getauthorversionpdf/C5CE00036J</ref>
}} }}

'''Dutasteride''', sold under the brand name '''Avodart''' among others, is a medication primarily used to treat the symptoms of a ] (BPH), an enlarged prostate not associated with cancer. A few months may be required before benefits occur.<ref name=BNF76/> It is also used for ] in men and as a part of ] in ].<ref name="ShapiroOtberg2015">{{Cite book |url=https://books.google.com/books?id=bJG9BwAAQBAJ&pg=PA39 |title=Hair Loss and Restoration, Second Edition |vauthors=Shapiro J, Otberg N |date=17 April 2015 |publisher=CRC Press |isbn=978-1-4822-3199-1 |pages=39– |access-date=27 October 2016 |archive-url=https://web.archive.org/web/20230112145741/https://books.google.com/books?id=bJG9BwAAQBAJ&pg=PA39 |archive-date=12 January 2023 |url-status=live}}</ref><ref name="Trans2017">{{Cite journal |vauthors=Wesp LM, Deutsch MB |date=March 2017 |title=Hormonal and Surgical Treatment Options for Transgender Women and Transfeminine Spectrum Persons |journal=The Psychiatric Clinics of North America |volume=40 |issue=1 |pages=99–111 |doi=10.1016/j.psc.2016.10.006 |pmid=28159148}}</ref> It is usually taken by mouth.<ref name="AHFS2019">{{Cite web |title=Dutasteride Monograph for Professionals |url=https://www.drugs.com/monograph/dutasteride.html |url-status=live |archive-url=https://web.archive.org/web/20190704111545/https://www.drugs.com/monograph/dutasteride.html |archive-date=4 July 2019 |access-date=18 March 2019 |website=Drugs.com |publisher=American Society of Health-System Pharmacists |language=en}}</ref><ref name="Wu2013">{{Cite journal |vauthors=Wu C, Kapoor A |date=July 2013 |title=Dutasteride for the treatment of benign prostatic hyperplasia |journal=Expert Opinion on Pharmacotherapy |volume=14 |issue=10 |pages=1399–1408 |doi=10.1517/14656566.2013.797965 |pmid=23750593 |s2cid=25041466}}</ref><ref name="BNF76">{{Cite book |title=British National Formulary : BNF 76 |date=2018 |publisher=Pharmaceutical Press |isbn=9780857113382 |edition=76 |pages=769}}</ref>

<!-- Side effects and mechanism -->
The most commonly reported side effects of dutasteride, although rare, include sexual dysfunction and ].<ref name=AHFS2019/> In the largest available study of 6,729 men with BPH, 9% experienced erectile dysfunction (compared to 5.7% treated with a ]), 3.3% experienced decreased ] (vs 1.6% of placebo), and 1.9% had ] (vs 1% of placebo).<ref name="Fertig2007DOJ">{{Cite journal |vauthors=Fertig RM, Gamret AC, Darwin E, Gaudi S |date=November 2017 |title=Sexual side effects of 5-α-reductase inhibitors finasteride and dutasteride: A comprehensive review |journal=Dermatology Online Journal |volume=23 |issue=11 |doi=10.5070/D32311037240 |pmid=29447628 |doi-access=free}}</ref><ref name="AndrioleREDUCE2010">{{Cite journal |vauthors=Andriole GL, Bostwick DG, Brawley OW, Gomella LG, Marberger M, Montorsi F, Pettaway CA, Tammela TL, Teloken C, Tindall DJ, Somerville MC, Wilson TH, Fowler IL, Rittmaster RS |date=April 2010 |title=Effect of dutasteride on the risk of prostate cancer |journal=The New England Journal of Medicine |volume=362 |issue=13 |pages=1192–1202 |doi=10.1056/NEJMoa0908127 |pmid=20357281 |doi-access=free}}</ref> Exposure during ] is specifically contraindicated because ]s such as dutasteride have been shown to interfere with the sexual development of male fetuses.<ref name="Blu2008">{{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=182, 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><ref name=AHFS2019/>

<!-- History, society, and culture -->
Dutasteride was patented in 1993 by ] and was approved for medical use in 2001.<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 |language=en |access-date=2020-09-19 |archive-url=https://web.archive.org/web/20230110031701/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA483 |archive-date=2023-01-10 |url-status=live}}</ref><ref name=AHFS2019/> In the United States and elsewhere, it is available as a ].<ref name=BNF76/> In 2018, it was the 291st-most commonly prescribed medication in the US with more than 1{{nbsp}}million prescriptions.<ref>{{Cite web |title=Dutasteride – Drug Usage Statistics |url=https://clincalc.com/DrugStats/Drugs/Dutasteride |url-status=live |archive-url=https://web.archive.org/web/20200206154756/https://clincalc.com/DrugStats/Drugs/Dutasteride |archive-date=6 February 2020 |access-date=7 October 2022 |website=ClinCalc}}</ref>

==Medical uses==

===Benign prostatic hyperplasia and prostate cancer===
Dutasteride is used for treating BPH, colloquially known as an "enlarged prostate".<ref name="Wu2013" /><ref>{{Cite journal |vauthors=Slater S, Dumas C, Bubley G |date=March 2012 |title=Dutasteride for the treatment of prostate-related conditions |journal=Expert Opinion on Drug Safety |volume=11 |issue=2 |pages=325–330 |doi=10.1517/14740338.2012.658040 |pmid=22316171 |s2cid=207487490}}</ref> It is approved by the ] (FDA) in the U.S. for this indication.<ref name="FDA">{{Cite web |title=Search Results for "DUTASTERIDE" |url=http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Set_Current_Drug&ApplNo=021319&DrugName=AVODART&ActiveIngred=DUTASTERIDE&SponsorApplicant=GLAXOSMITHKLINE&ProductMktStatus=1&goto=Search.DrugDetails |url-status=live |archive-url=https://web.archive.org/web/20210829124132/https://www.accessdata.fda.gov/scripts/cder/daf/ |archive-date=2021-08-29 |access-date=2016-10-29 |website=Drugs@FDA: FDA Approved Drug Products}}</ref> A 2010 ] found a 25–26% reduction in the risk of developing ] with 5α-reductase inhibitor ].<ref name="pmid20977593">{{Cite journal |vauthors=Wilt TJ, Macdonald R, Hagerty K, Schellhammer P, Tacklind J, Somerfield MR, Kramer BS |date=November 2010 |title=5-α-Reductase inhibitors for prostate cancer chemoprevention: an updated Cochrane systematic review |journal=BJU International |volume=106 |issue=10 |pages=1444–1451 |doi=10.1111/j.1464-410X.2010.09714.x |pmid=20977593 |s2cid=22178061}}</ref>

===Scalp hair loss and excessive hair growth===
Dutasteride is approved for the treatment of male androgenetic alopecia in ] and ] at a dosage of 0.5&nbsp;mg per day.<ref name="ShapiroOtberg2015" /><ref name="pmid27489426" /> Several studies have found it to induce hair regrowth in men more rapidly and to a greater extent than even the highest approved dosage of ].<ref name="ShapiroOtberg2015" /><ref name="pmid32279398">{{Cite journal |vauthors=Dhurat R, Sharma A, Rudnicka L, Kroumpouzos G, Kassir M, Galadari H, Wollina U, Lotti T, Golubovic M, Binic I, Grabbe S, Goldust M |date=May 2020 |title=5-Alpha reductase inhibitors in androgenetic alopecia: Shifting paradigms, current concepts, comparative efficacy, and safety |journal=Dermatologic Therapy |volume=33 |issue=3 |pages=e13379 |doi=10.1111/dth.13379 |pmid=32279398 |s2cid=215748750 |doi-access=free}}</ref><ref name="pmid30863034">{{Cite journal |vauthors=Zhou Z, Song S, Gao Z, Wu J, Ma J, Cui Y |date=2019 |title=The efficacy and safety of dutasteride compared with finasteride in treating men with androgenetic alopecia: a systematic review and meta-analysis |journal=Clinical Interventions in Aging |volume=14 |pages=399–406 |doi=10.2147/CIA.S192435 |pmc=6388756 |pmid=30863034 |doi-access=free}}</ref><ref name="pmid17110217">{{Cite journal |vauthors=Olsen EA, Hordinsky M, Whiting D, Stough D, Hobbs S, Ellis ML, Wilson T, Rittmaster RS |date=December 2006 |title=The importance of dual 5alpha-reductase inhibition in the treatment of male pattern hair loss: results of a randomized placebo-controlled study of dutasteride versus finasteride |journal=Journal of the American Academy of Dermatology |volume=55 |issue=6 |pages=1014–1023 |doi=10.1016/j.jaad.2006.05.007 |pmid=17110217}}</ref> The superior effectiveness of dutasteride relative to finasteride for this indication is because the inhibition of 5α-reductase and consequent reduction of ] (DHT) production within the hair follicles is more complete with dutasteride. Dutasteride is also used off-label in the treatment of female pattern hair loss.<ref name="pmid24017975" /><ref name="CarminaAzziz2019">{{Cite journal |vauthors=Carmina E, Azziz R, Bergfeld W, Escobar-Morreale HF, Futterweit W, Huddleston H, Lobo R, Olsen E |date=July 2019 |title=Female Pattern Hair Loss and Androgen Excess: A Report From the Multidisciplinary Androgen Excess and PCOS Committee |journal=The Journal of Clinical Endocrinology and Metabolism |volume=104 |issue=7 |pages=2875–2891 |doi=10.1210/jc.2018-02548 |pmid=30785992 |doi-access=free}}</ref>

Other 5α-reductase inhibitors such as finasteride (a type 2 inhibitor) have been used ] to treat excessive hair growth in women with ].<ref name="Blu2008" /><ref name="Martin2018">{{Cite journal |vauthors=Martin KA, Chang RJ, Ehrmann DA, Ibanez L, Lobo RA, Rosenfield RL, Shapiro J, Montori VM, Swiglo BA |date=April 2008 |title=Evaluation and treatment of hirsutism in premenopausal women: an endocrine society clinical practice guideline |journal=The Journal of Clinical Endocrinology and Metabolism |volume=93 |issue=4 |pages=1105–1120 |doi=10.1210/jc.2018-00241 |pmid=18252793 |doi-access=free}}</ref> Since dutasteride is an inhibitor of both type 1 and 2 5α-reductases, it could theoretically be a more effective therapy for hirsutism. However, dutasteride is not recommended for this indication due to a lack of supportive clinical evidence and a substantial risk of birth defects in female patients who inadvertently become pregnant.<ref name="Martin2018" /><ref name="LebwohlHeymann2013">{{Cite book |url=https://books.google.com/books?id=hRryAAAAQBAJ&pg=PA327 |title=Treatment of Skin Disease: Comprehensive Therapeutic Strategies |vauthors=Lebwohl MG, Heymann WR, Berth-Jones J, Coulson I |date=19 September 2013 |publisher=Elsevier Health Sciences |isbn=978-0-7020-5236-1 |pages=327– |access-date=10 December 2016 |archive-url=https://web.archive.org/web/20230112145741/https://books.google.com/books?id=hRryAAAAQBAJ&pg=PA327 |archive-date=12 January 2023 |url-status=live}}</ref>

===Transgender hormone therapy===
Dutasteride is sometimes used as a component of ] for ] in combination with an ] and/or another ] such as ].<ref name="Trans2017" /> It may be useful for treating scalp hair loss or in those who have issues tolerating spironolactone.<ref name="Trans2017" />

===Available forms===
Dutasteride is provided in the form of soft, ]-filled ] ]s containing 0.5&nbsp;mg dutasteride each.<ref name="FDALabel" />

==Contraindications==
Women who are or who may become ] should not handle the drug. Dutasteride can cause ]s in male ]es, specifically ] and undermasculinization.<ref name="FDALabel" /><ref name="McVaryWelliver2016">{{Cite book |url=https://books.google.com/books?id=OkLUDAAAQBAJ&pg=PA396 |title=Treatment of Lower Urinary Tract Symptoms and Benign Prostatic Hyperplasia: Current methods, outcomes, and controversies, An Issue of Urologic Clinics of North America, E-Book |vauthors=McVary KT, Welliver C |date=12 August 2016 |publisher=Elsevier Health Sciences |isbn=978-0-323-45994-5 |pages=396– |access-date=10 December 2017 |archive-url=https://web.archive.org/web/20230112145741/https://books.google.com/books?id=OkLUDAAAQBAJ&pg=PA396 |archive-date=12 January 2023 |url-status=live}}</ref> This is due to its antiandrogenic effects similar to what is seen in ].<ref name="McVaryWelliver2016" /> For the same reason, women who are currently pregnant should never take dutasteride.<ref name="FDALabel" /> People taking dutasteride should not ] to prevent birth defects if a pregnant woman receives blood and should also not donate blood for at least 6&nbsp;months after the cessation of treatment due to the drug's long ].<ref name="FDALabel"/>

Children and people with known significant ] (e.g., serious ]s, ]) to dutasteride should not take it.<ref name="FDALabel">{{Cite web |last=<!--Staff writer(s); no by-line.--> |date=June 2011 |title=AVODART (dutasteride) Soft Gelatin Capsules Prescribing information |url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021319s023s025lbl.pdf |url-status=live |archive-url=https://web.archive.org/web/20130307020555/http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021319s023s025lbl.pdf |archive-date=7 March 2013 |access-date=15 September 2013 |website=GlaxoSmithKline |publisher=U.S. Food and Drug Administration}}</ref>

==Adverse effects==
Dutasteride has overall been found to be ] in studies of both men and women, producing minimal ]s.<ref name="Hirs2016">{{Cite journal |vauthors=Hirshburg JM, Kelsey PA, Therrien CA, Gavino AC, Reichenberg JS |date=July 2016 |title=Adverse Effects and Safety of 5-alpha Reductase Inhibitors (Finasteride, Dutasteride): A Systematic Review |journal=The Journal of Clinical and Aesthetic Dermatology |volume=9 |issue=7 |pages=56–62 |pmc=5023004 |pmid=27672412}}</ref> Adverse effects include ] and ].<ref name="Hirs2016" /> Isolated reports of ] changes, ], and ] also exist.<ref name="Hirs2016" /> A small risk of sexual side effects has been documented in men taking the drug during the first few months of therapy.<ref name="Hirs2016" /><ref name="pmid27784557">{{Cite journal |vauthors=Trost L, Saitz TR, Hellstrom WJ |date=May 2013 |title=Side Effects of 5-Alpha Reductase Inhibitors: A Comprehensive Review |journal=Sexual Medicine Reviews |volume=1 |issue=1 |pages=24–41 |doi=10.1002/smrj.3 |pmid=27784557}}</ref>

The FDA added a ] to dutasteride in 2011 describing an increased risk of high-grade prostate cancer in those who take the drug.<ref>{{Cite web |date=18 June 2019 |title=FDA Drug Safety Communication: 5-alpha reductase inhibitors (5-ARIs) may increase the risk of a more serious form of prostate cancer |url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-5-alpha-reductase-inhibitors-5-aris-may-increase-risk-more-serious |url-status=live |archive-url=https://web.archive.org/web/20210309192037/https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-5-alpha-reductase-inhibitors-5-aris-may-increase-risk-more-serious |archive-date=9 March 2021 |access-date=9 March 2021 |newspaper=U.S. Food and Drug Administration}}</ref> No direct mechanistic link between 5α-reductase inhibitors and prostate cancer has been established.<ref name="AUAGuideline2021" /> This is not due to a direct link between dutasteride or other 5α-reductase inhibitors and cancer ''per se'', but rather that those who take 5α-reductase inhibitors may have a decrease in ] (PSA) levels, and therefore increases in PSA (which are an indicator of possible cancer) may be masked in those who take the drug.<ref name="Sarkar2019">{{Cite journal |vauthors=Sarkar RR, Parsons JK, Bryant AK, Ryan ST, Kader AK, McKay RR, D'Amico AV, Nguyen PL, Hulley BJ, Einck JP, Mundt AJ, Kane CJ, Murphy JD, Rose BS |date=June 2019 |title=Association of Treatment With 5α-Reductase Inhibitors With Time to Diagnosis and Mortality in Prostate Cancer |journal=JAMA Internal Medicine |volume=179 |issue=6 |pages=812–819 |doi=10.1001/jamainternmed.2019.0280 |pmc=6503564 |pmid=31058923}}</ref> This is thought to delay cancer diagnosis so that patients taking 5α-reductase inhibitors present with a ] tumor at the time of diagnosis. The ] <!-- (AUA) --> advises that increased risk for patients taking these drugs leads to higher prostate cancer-specific and ].<ref name="AUAGuideline2021">{{Cite journal |vauthors=Lerner LB, McVary KT, Barry MJ, Bixler BR, Dahm P, Das AK, Gandhi MC, Kaplan SA, Kohler TS, Martin L, Parsons JK, Roehrborn CG, Stoffel JT, Welliver C, Wilt TJ |date=October 2021 |title=Management of Lower Urinary Tract Symptoms Attributed to Benign Prostatic Hyperplasia: AUA GUIDELINE PART I-Initial Work-up and Medical Management |journal=The Journal of Urology |volume=206 |issue=4 |pages=806–817 |doi=10.1097/JU.0000000000002183 |pmid=34384237 |s2cid=236999299}}</ref> The AUA also advises that this affect can be alleviated with more frequent screening and lower PSA cutoffs for diagnostic biopsies in men taking dutasteride or other 5α-reductase inhibitors.<ref name="AUAGuideline2021" /> Dutasteride is known to reduce the growth and prevalence of benign prostate tumors.<ref name="Walsh2010">{{Cite journal |vauthors=Walsh PC |date=April 2010 |title=Chemoprevention of prostate cancer |journal=The New England Journal of Medicine |volume=362 |issue=13 |pages=1237–1238 |doi=10.1056/NEJMe1001045 |pmid=20357287}}</ref> A 2018 ] found no higher risk of ] with 5α-reductase inhibitors.<ref name="pmid29697934">{{Cite journal |vauthors=Wang J, Zhao S, Luo L, Li E, Li X, Zhao Z |date=2018 |title=5-alpha Reductase Inhibitors and risk of male breast cancer: a systematic review and meta-analysis |journal=International Braz J Urol |volume=44 |issue=5 |pages=865–873 |doi=10.1590/S1677-5538.IBJU.2017.0531 |pmc=6237523 |pmid=29697934}}</ref>

] and mood side effects, such as erectile dysfunction,<ref name="Fertig2017">{{Cite journal |vauthors=Fertig R, Shapiro J, Bergfeld W, Tosti A |date=January 2017 |title=Investigation of the Plausibility of 5-Alpha-Reductase Inhibitor Syndrome |journal=Skin Appendage Disorders |volume=2 |issue=3–4 |pages=120–129 |doi=10.1159/000450617 |pmc=5264352 |pmid=28232919}}</ref> ],<ref name="Traish2015">{{Cite journal |vauthors=Traish AM, Melcangi RC, Bortolato M, Garcia-Segura LM, Zitzmann M |date=September 2015 |title=Adverse effects of 5α-reductase inhibitors: What do we know, don't know, and need to know? |journal=Reviews in Endocrine & Metabolic Disorders |volume=16 |issue=3 |pages=177–198 |doi=10.1007/s11154-015-9319-y |pmid=26296373 |s2cid=25002351}}</ref> ],<ref name="Tra2011">{{Cite journal |vauthors=Traish AM, Hassani J, Guay AT, Zitzmann M, Hansen ML |date=March 2011 |title=Adverse side effects of 5α-reductase inhibitors therapy: persistent diminished libido and erectile dysfunction and depression in a subset of patients |journal=The Journal of Sexual Medicine |volume=8 |issue=3 |pages=872–884 |doi=10.1111/j.1743-6109.2010.02157.x |pmid=21176115}}</ref> and ] occur in as many as 4.8% of patients taking 5α-reductase inhibitors including dutasteride.<ref name="pmid24955220">{{Cite journal |vauthors=Traish AM, Mulgaonkar A, Giordano N |date=June 2014 |title=The dark side of 5α-reductase inhibitors' therapy: sexual dysfunction, high Gleason grade prostate cancer and depression |journal=Korean Journal of Urology |volume=55 |issue=6 |pages=367–379 |doi=10.4111/kju.2014.55.6.367 |pmc=4064044 |pmid=24955220}}</ref><ref name="Traish2015" /> In affected men, semen volume is decreased an average of 30%,<ref name="Samaplaski 2013">{{Cite journal |vauthors=Samplaski MK, Lo K, Grober E, Jarvi K |date=December 2013 |title=Finasteride use in the male infertility population: effects on semen and hormone parameters |journal=Fertility and Sterility |volume=100 |issue=6 |pages=1542–1546 |doi=10.1016/j.fertnstert.2013.07.2000 |pmid=24012200 |doi-access=free}}</ref> with a smaller subgroup of patients also experiencing a decrease of sperm motility of 6 to 12%.<ref name="Amory2007">{{Cite journal |vauthors=Amory JK, Wang C, Swerdloff RS, Anawalt BD, Matsumoto AM, Bremner WJ, Walker SE, Haberer LJ, Clark RV |date=May 2007 |title=The effect of 5alpha-reductase inhibition with dutasteride and finasteride on semen parameters and serum hormones in healthy men |journal=The Journal of Clinical Endocrinology and Metabolism |volume=92 |issue=5 |pages=1659–1665 |doi=10.1210/jc.2006-2203 |pmid=17299062}}</ref><ref name="Millsop2013" /> Sperm shape and function are unaffected and the impact on male fertility is unknown.<ref name="Semet2017">{{Cite journal |vauthors=Semet M, Paci M, Saïas-Magnan J, Metzler-Guillemain C, Boissier R, Lejeune H, Perrin J |date=July 2017 |title=The impact of drugs on male fertility: a review |journal=Andrology |volume=5 |issue=4 |pages=640–663 |doi=10.1111/andr.12366 |pmid=28622464 |s2cid=37989045 |doi-access=free}}</ref> These negative effects reverse by 3–4 months after discontinuation of the drug.<ref name="Semet2017" /><ref name="Millsop2013">{{Cite journal |vauthors=Millsop JW, Heller MM, Eliason MJ, Murase JE |date=July 2013 |title=Dermatological medication effects on male fertility |journal=Dermatologic Therapy |volume=26 |issue=4 |pages=337–346 |doi=10.1111/dth.12069 |pmid=23914891 |s2cid=9087715 |doi-access=free}}</ref><ref name="AUAGuideline2021" />

In a study of 6,729 men with ] (BPH, a condition where the prostate grows unassociated with ]), 9% had ] (compared to 5.7% treated with a ]), 3.3% experienced decreased ] (vs 1.6% of placebo), and 1.9% had ] (vs 1% of placebo).<ref name="Fertig2017" /><ref name="AndrioleREDUCE2010" /> These effects were noted to resolve over time, with many fewer men reporting any adverse effects by the end of the 4-year study.<ref name="AndrioleREDUCE2010" /><ref name="Fertig2017" /> The rate of discontinuation of the drug due to adverse effects was less than 5%.<ref name="AndrioleREDUCE2010" />

A subset of men affected by sexual and mood side effects report persistent loss of libido,<ref name="Fertig2017" /> depression,<ref name="Hirs2016" /> and erectile dysfunction for several years after discontinuing treatment.<ref name="Traish2015" /> This remains a highly contested topic in the academic literature due to disagreements about whether the ] effect may play a role,<ref name="ThanRodriguezKhera2018">{{Cite journal |vauthors=Than JK, Rodriguez K, Khera M |date=24 July 2018 |title=Post-finasteride Syndrome: A Review of Current Literature |journal=Current Sexual Health Reports |volume=10 |issue=3 |pages=152–157 |doi=10.1007/s11930-018-0163-4 |issn=1548-3584 |eissn=1548-3592 |s2cid=81968700}}</ref><ref name="SaengmearnuparpLojanapiwatChattipakorn2021">{{Cite journal |vauthors=Saengmearnuparp T, Lojanapiwat B, Chattipakorn N, Chattipakorn S |date=November 2021 |title=The connection of 5-alpha reductase inhibitors to the development of depression |journal=Biomedicine & Pharmacotherapy |volume=143 |pages=112100 |doi=10.1016/j.biopha.2021.112100 |pmid=34479019 |doi-access=free}}</ref><ref name="Coskuner2019">{{Cite journal |vauthors=Coskuner ER, Ozkan B, Culha MG |date=April 2019 |title=Sexual Problems of Men With Androgenic Alopecia Treated With 5-Alpha Reductase Inhibitors |journal=Sexual Medicine Reviews |volume=7 |issue=2 |pages=277–282 |doi=10.1016/j.sxmr.2018.07.003 |pmid=30301703 |s2cid=52946784}}</ref> whether self-report questionnaires are reliable for this data,<ref name="AUAGuideline2021" /> and whether enough objective evidence exists to conclude these effects are persistent after discontinuation of the drug.<ref name="AUAGuideline2021" /><ref name="Traish 2020">{{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><ref name="Liu2016">{{Cite journal |vauthors=Liu L, Zhao S, Li F, Li E, Kang R, Luo L, Luo J, Wan S, Zhao Z |date=September 2016 |title=Effect of 5α-Reductase Inhibitors on Sexual Function: A Meta-Analysis and Systematic Review of Randomized Controlled Trials |journal=The Journal of Sexual Medicine |volume=13 |issue=9 |pages=1297–1310 |doi=10.1016/j.jsxm.2016.07.006 |pmid=27475241}}</ref> The Post-Finasteride Syndrome Foundation (PFSF) was created with a medical advisory board to study the topic (finasteride is a similar 5α-reductase inhibitor)<ref>{{Cite web |title=The Post-Finasteride Syndrome Foundation – Dedicated to supporting research and finding treatments for PFS patients worldwide. |url=https://www.pfsfoundation.org/ |url-status=live |archive-url=https://web.archive.org/web/20211221100527/https://www.pfsfoundation.org/ |archive-date=2021-12-21 |access-date=2021-12-24 |language=en-US}}</ref> and lawsuits alleging harm from the drug are ongoing.<ref>{{Cite news |date=2021-09-08 |title=Group sues to have hair-loss drug Propecia pulled from market |url=https://www.reuters.com/legal/litigation/group-sues-have-hair-loss-drug-propecia-pulled-market-2021-09-08/ |url-status=live |archive-url=https://web.archive.org/web/20211224165809/https://www.reuters.com/legal/litigation/group-sues-have-hair-loss-drug-propecia-pulled-market-2021-09-08/ |archive-date=2021-12-24 |access-date=2021-12-24 |work=Reuters |language=en |vauthors=Pierson B}}</ref> Concerns from the PFSF and other patient advocates led the FDA to add a black-box warning to Finasteride for possible risks of suicide in June 2022.<ref name="AUAGuideline2021" /><ref name="Levine2022Reuters">{{Cite news |date=10 June 2022 |title=FDA requires disclosure of suicide risk for anti-baldness drug |url=https://www.reuters.com/business/healthcare-pharmaceuticals/fda-requires-disclosure-suicide-risk-anti-baldness-drug-2022-06-10/ |url-status=live |archive-url=https://web.archive.org/web/20221112200941/https://www.reuters.com/business/healthcare-pharmaceuticals/fda-requires-disclosure-suicide-risk-anti-baldness-drug-2022-06-10/ |archive-date=12 November 2022 |access-date=12 November 2022 |work=Reuters |language=en |vauthors=Levine D}}</ref> Some experts have questioned the basis of the black-box warning, given that it relies on anecdotal patient-reported outcomes rather than prospective trials.<ref name="AUAGuideline2021" />

==Overdose==
No specific ] for ] of dutasteride is known, since the drug is extremely safe and well tolerated. Research studies show that even at 100 times the normal dose, dutasteride is not lethal.<ref name="Avodart-Label">{{Cite web |title=AVODART (dutasteride) Soft Gelatin Capsules Prescribing information |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021319s028s029lbl.pdf |url-status=live |archive-url=https://web.archive.org/web/20210403220821/https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021319s028s029lbl.pdf |archive-date=2021-04-03 |access-date=2020-01-10 |website=GlaxoSmithKline |publisher=U.S. Food and Drug Administration}}</ref> Treatment of dutasteride overdose should be based on ]s and should be with supportive therapies.<ref name="Avodart-Label" /> The long elimination half-life of dutasteride should be taken into consideration in the event of an overdose of the medication.<ref name="Avodart-Label" /> Dutasteride has been used in clinical studies at doses of up to 40&nbsp;mg/day for a week (80&nbsp;times the therapeutic dosage) and 5&nbsp;mg/day for 6&nbsp;months (10&nbsp;times the therapeutic dosage) with no significant ] concerns or additional side effects.<ref name="Avodart-Label" />

== Current investigations ==
Dutasteride has been studied in combination with ] in the treatment of prostate cancer.<ref name="pmid26048455">{{Cite journal |vauthors=Chu FM, Sartor O, Gomella L, Rudo T, Somerville MC, Hereghty B, Manyak MJ |date=August 2015 |title=A randomised, double-blind study comparing the addition of bicalutamide with or without dutasteride to GnRH analogue therapy in men with non-metastatic castrate-resistant prostate cancer |journal=European Journal of Cancer |volume=51 |issue=12 |pages=1555–1569 |doi=10.1016/j.ejca.2015.04.028 |pmid=26048455}}</ref><ref name="pmid26702991">{{Cite journal |vauthors=Gaudet M, Vigneault É, Foster W, Meyer F, Martin AG |date=January 2016 |title=Randomized non-inferiority trial of Bicalutamide and Dutasteride versus LHRH agonists for prostate volume reduction prior to I-125 permanent implant brachytherapy for prostate cancer |journal=Radiotherapy and Oncology |volume=118 |issue=1 |pages=141–147 |doi=10.1016/j.radonc.2015.11.022 |pmid=26702991}}</ref><ref name="pmid27330919">{{Cite journal |vauthors=Dijkstra S, Witjes WP, Roos EP, Vijverberg PL, Geboers AD, Bruins JL, Smits GA, Vergunst H, Mulders PF |year=2016 |title=The AVOCAT study: Bicalutamide monotherapy versus combined bicalutamide plus dutasteride therapy for patients with locally advanced or metastatic carcinoma of the prostate-a long-term follow-up comparison and quality of life analysis |journal=SpringerPlus |volume=5 |pages=653 |doi=10.1186/s40064-016-2280-8 |pmc=4870485 |pmid=27330919 |doi-access=free}}</ref>

Ongoing clinical trials are investigating whether dutasteride may be an effective treatment for ] (PMDD), because dutasteride may inhibit the conversion of ] to ], a ] ], which may be responsible for some of the debilitating symptoms of PMDD.<ref name="pmid26766596">{{Cite journal |vauthors=Pearlstein T |date=April 2016 |title=Treatment of Premenstrual Dysphoric Disorder: Therapeutic Challenges |journal=Expert Review of Clinical Pharmacology |volume=9 |issue=4 |pages=493–496 |doi=10.1586/17512433.2016.1142371 |pmid=26766596 |quote=A recent study with a 5α-reductase inhibitor dutasteride, that blocks the conversion of progesterone to ALLO, reported that dutasteride 2.5 mg daily decreased several premenstrual symptoms |doi-access=free}}</ref><ref name="PsychBullNaguy2022">{{Cite journal |vauthors=Naguy A, El-Sheshai A, Thiguti SH, Alamiri B |date=June 2022 |title=Psychopharmacotherapy of Premenstrual Dysphoric Disorder-''New Vistas'' |journal=Psychopharmacology Bulletin |volume=52 |issue=3 |pages=81–83 |pmc=9235312 |pmid=35815174 |quote=Capitalizing on this premise, agents in the pipeline for PMDD including dutasteride, ulipristal acetate, and sepranolone are promising. Dutasteride, FDA-approved for benign prostatic hyperplasia, is a 5-α reductase inhibitor; the latter catalyzes the rate-limiting step in metabolism of progesterone to allopregnanolone...Two double-blind RCTs, cross-over trials, support use of dutasteride where high-dose (2.5 mg/d) outperforms placebo.}}</ref>

==Pharmacology==

===Pharmacodynamics===
Dutasteride belongs to a class of drugs called 5α-reductase inhibitors, which block the action of the 5α-reductase enzymes that convert testosterone into DHT.<ref name="BostwickCheng2014">{{Cite book |url=https://books.google.com/books?id=wrHQAgAAQBAJ&pg=PA492 |title=Urologic Surgical Pathology |vauthors=Bostwick DG, Cheng L |date=24 January 2014 |publisher=Elsevier Health Sciences |isbn=978-0-323-08619-6 |pages=492–}}</ref> It ]s all three ]s of 5α-reductase, and can decrease DHT levels in the blood by up to 98%.<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 |pages=1286–1287 |access-date=2017-12-06 |archive-url=https://web.archive.org/web/20230110031700/https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA1286 |archive-date=2023-01-10 |url-status=live}}</ref><ref name="Yamana2010">{{Cite journal |vauthors=Yamana K, Labrie F, Luu-The V |date=August 2010 |title=Human type 3 5α-reductase is expressed in peripheral tissues at higher levels than types 1 and 2 and its activity is potently inhibited by finasteride and dutasteride |journal=Hormone Molecular Biology and Clinical Investigation |volume=2 |issue=3 |pages=293–299 |doi=10.1515/hmbci.2010.035 |pmid=25961201 |s2cid=28841145}}</ref><ref name="Bradbury2007">{{Cite book |url=https://books.google.com/books?id=fdtDAAAAQBAJ&pg=PA49 |title=Cancer |vauthors=Bradbury R |date=30 January 2007 |publisher=Springer Science & Business Media |isbn=978-3-540-33120-9 |pages=49–}}</ref> Specifically it is a ], ] (]) inhibitor of all three ]s of 5α-reductase, ], ], and ] ({{abbrlink|IC<sub>50</sub>|Half-maximal inhibitory concentration}} values are 3.9&nbsp;nM for type I and 1.8&nbsp;nM for type II).<ref name="LemkeWilliams2008" /><ref name="Yamana2010" /><ref name="pmid18318566">{{Cite journal |vauthors=Keam SJ, Scott LJ |year=2008 |title=Dutasteride: a review of its use in the management of prostate disorders |journal=Drugs |volume=68 |issue=4 |pages=463–485 |doi=10.2165/00003495-200868040-00008 |pmid=18318566 |s2cid=242987808}}</ref><ref name="pmid9871428">{{Cite journal |vauthors=Gisleskog PO, Hermann D, Hammarlund-Udenaes M, Karlsson MO |date=December 1998 |title=A model for the turnover of dihydrotestosterone in the presence of the irreversible 5 alpha-reductase inhibitors GI198745 and finasteride |journal=Clinical Pharmacology and Therapeutics |volume=64 |issue=6 |pages=636–647 |doi=10.1016/S0009-9236(98)90054-6 |pmid=9871428 |s2cid=42901328}}</ref> This is in contrast to finasteride, which is similarly an irreversible inhibitor of 5α-reductase but only inhibits the type II and III ]s.<ref name="pmid9871428" /><ref name="KeserüSwinney2015">{{Cite book |url=https://books.google.com/books?id=7WpICgAAQBAJ&pg=PA165 |title=Thermodynamics and Kinetics of Drug Binding |vauthors=Keserü G, Swinney DC |date=28 July 2015 |publisher=Wiley |isbn=978-3-527-67304-9 |pages=165–}}</ref><ref name="Yamana2010" /> As a result of this difference, dutasteride is able to achieve a reduction in circulating DHT levels of up to 98%, whereas finasteride is able to achieve a reduction of only 65 to 70%.<ref name="Bradbury2007" /><ref name="BurchumRosenthal2014" /><ref name="BostwickCheng2014" /><ref name="HeesakkersChapple2016">{{Cite book |url=https://books.google.com/books?id=aWKhCwAAQBAJ&pg=PA280 |title=Practical Functional Urology |vauthors=Heesakkers J, Chapple C, De Ridder D, Farag F |date=24 February 2016 |publisher=Springer |isbn=978-3-319-25430-2 |pages=280–}}</ref> In spite of the differential reduction in circulating DHT levels, the two drugs decrease levels of DHT to a similar extent of approximately 85 to 90% in the ],<ref name="HeesakkersChapple2016" /> where the type II isoform predominates.<ref name="pmid18318566" />

Since 5α-reductases degrade testosterone to DHT, the inhibition of these enzymes could theoretically cause an increase in testosterone. A 2018 review found that initiation of 5α-reductase inhibitors did not result in a consistent increase in testosterone levels.<ref name="Traish2019">{{Cite journal |vauthors=Traish AM, Krakowsky Y, Doros G, Morgentaler A |date=January 2019 |title=Do 5α-Reductase Inhibitors Raise Circulating Serum Testosterone Levels? A Comprehensive Review and Meta-Analysis to Explaining Paradoxical Results |journal=Sexual Medicine Reviews |volume=7 |issue=1 |pages=95–114 |doi=10.1016/j.sxmr.2018.06.002 |pmid=30098986 |s2cid=51968365}}</ref> Among the studies analyzed, there was no statistically significant change in testosterone levels from 5α-reductase inhibitors overall, though men with lower baseline testosterone levels did show an increase.<ref name="Traish2019" />

In addition to inhibition of DHT production, 5α-reductase inhibitors such as dutasteride are also ]s, preventing the 5α-reductase-mediated biosynthesis of various neurosteroids, including allopregnanolone (from progesterone), {{abbrlink|THDOC|tetrahydrodeoxycorticosterone}} (from ]), and ] (from testosterone).<ref name="pmid24955220" /> These neurosteroids are potent ]s of the ] and have shown ], ], and ] effects in ].<ref name="pmid24955220" /><ref name="Weizman2008">{{Cite book |url=https://books.google.com/books?id=uABKkFdPjhkC |title=Neuroactive Steroids in Brain Function, Behavior and Neuropsychiatric Disorders: Novel Strategies for Research and Treatment |vauthors=Weizman A |date=1 February 2008 |publisher=Springer Science & Business Media |isbn=978-1-4020-6854-6}}</ref><ref name="TvrdeićPoljak2016">{{Cite journal |vauthors=Tvrdeić A, Poljak L |year=2016 |title=Neurosteroids, GABAA receptors and neurosteroid based drugs: are we witnessing the dawn of the new psychiatric drugs? |journal=Endocrine Oncology and Metabolism |volume=2 |issue=1 |pages=60–71 |doi=10.21040/eom/2016.2.7 |doi-broken-date=1 November 2024 |doi-access=free}}</ref> For this reason, decreased neurosteroid production is one hypothesized mechanism for sexual dysfunction and depression associated with 5α-reductase inhibitors such as dutasteride.<ref name="pmid24955220" />

===Pharmacokinetics===
The oral ] of dutasteride is about 60%.<ref name="LemkeWilliams2008" /> Consumption with food does not adversely affect its ].<ref name="LemkeWilliams2008" /> ] occur 2 to 3&nbsp;hours after administration.<ref name="LemkeWilliams2008" /> Dutasteride is present in ] at levels up to 3&nbsp;ng/ml, with no significant effects on DHT levels of sexual partners.<ref name="LemkeWilliams2008" /> The drug is extensively ] in the ] by '']''.<ref name="LemkeWilliams2008" /> It has three major metabolites: 6'-hydroxydutasteride, 4'-hydroxydutasteride, and 1,2-dihydrodutasteride. The former two are formed by ''CYP3A4'', while the latter is not.<ref name="LemkeWilliams2008" /> All three metabolites are active; 6'-hydroxydutasteride has similar 5α-reductase inhibitor ] as dutasteride, while the other two are less potent.<ref name="LemkeWilliams2008" /> Dutasteride has an extremely long ] or elimination half-life of about 4 to 5&nbsp;weeks.<ref name="BurchumRosenthal2014">{{Cite book |url=https://books.google.com/books?id=C7_NBQAAQBAJ&pg=PA803 |title=Lehne's Pharmacology for Nursing Care |vauthors=Burchum J, Rosenthal L |date=2 December 2014 |publisher=Elsevier Health Sciences |isbn=978-0-323-34026-7 |pages=803– |access-date=27 October 2016 |archive-url=https://web.archive.org/web/20230112145742/https://books.google.com/books?id=C7_NBQAAQBAJ&pg=PA803 |archive-date=12 January 2023 |url-status=live}}</ref><ref name="Blu2008" /> Its elimination half-life is increased in the elderly (170&nbsp;hours for men aged 20–49&nbsp;years, 300&nbsp;hours for men aged >70&nbsp;years).<ref name="LemkeWilliams2008" /> No dosage adjustment is necessary in the elderly nor in patients with ].<ref name="LemkeWilliams2008" /> Because of its long elimination half-life, dutasteride requires 5 to 6&nbsp;months to reach ] concentrations.<ref name="pmid18318566" /> It also remains in the body for a long time after discontinuation and can be detected up to 4 to 6&nbsp;months.<ref name="LemkeWilliams2008" /><ref name="BurchumRosenthal2014" /> In contrast to dutasteride, finasteride has a short terminal half-life of only 5 to 8&nbsp;hours.<ref name="Blu2008" /><ref name="LemkeWilliams2008" /> Dutasteride is ] mainly in the ] (40%) as metabolites.<ref name="LemkeWilliams2008" /> A smaller portion (5%) is eliminated unchanged in the ].<ref name="LemkeWilliams2008" />

==Chemistry==
{{See also|List of 5α-reductase inhibitors}}

Dutasteride, also known as ''N''--3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide, is a ] ] ] and a ].<ref name="LemkeWilliams2012">{{Cite book |url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1381 |title=Foye's Principles of Medicinal Chemistry |vauthors=Lemke TL, Williams DA |date=24 January 2012 |publisher=Lippincott Williams & Wilkins |isbn=978-1-60913-345-0 |pages=1381–}}</ref><ref name="Ravina2011">{{Cite book |url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA183 |title=The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs |vauthors=Ravina E |date=11 January 2011 |publisher=John Wiley & Sons |isbn=978-3-527-32669-3 |pages=183–}}</ref> It is an ] of finasteride in which the ''tert''-butyl amide ] has been replaced with a 2,5-''bis''(trifluoromethyl)phenyl ].<ref name="Ravina2011" />

==History==
Dutasteride was ]ed in 1996 and was first described in the ] in 1997.<ref name="Drugs.com" /><ref name="Llewellyn2011" /> It was approved by the FDA for the treatment of BPH in November 2001, and was introduced on the United States market the following year under the brand name Avodart.<ref name="Llewellyn2011" /> Dutasteride has subsequently been introduced in many other countries, including throughout Europe and South America.<ref name="Llewellyn2011">{{Cite book |url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT971 |title=Anabolics |vauthors=Llewellyn W |publisher=Molecular Nutrition Llc |year=2011 |isbn=978-0-9828280-1-4 |pages=968–,971– |access-date=2017-12-11 |archive-url=https://web.archive.org/web/20230112145743/https://books.google.com/books?id=afKLA-6wW0oC&pg=PT971 |archive-date=2023-01-12 |url-status=live}}</ref> The ] of dutasteride expired in November 2015, so the drug has since become available in the United States in a variety of low-cost ]s.<ref name="Drugs.com">{{Cite web |title=Generic Avodart Availability |url=https://www.drugs.com/availability/generic-avodart.html |url-status=live |archive-url=https://web.archive.org/web/20161220231141/https://www.drugs.com/availability/generic-avodart.html |archive-date=2016-12-20 |access-date=2016-12-10 |website=Drugs.com}}</ref>

It was approved for the treatment of scalp hair loss in South Korea in 2009 and in Japan in 2015.<ref>{{Cite web |date=3 December 2015 |title=GSK Japan delays alopecia drug launch after Catalent manufacturing halt |url=http://www.in-pharmatechnologist.com/Regulatory-Safety/GSK-Japan-delays-alopecia-drug-launch-after-Catalent-manufacturing-halt |url-status=live |archive-url=https://web.archive.org/web/20161001165059/http://www.in-pharmatechnologist.com/Regulatory-Safety/GSK-Japan-delays-alopecia-drug-launch-after-Catalent-manufacturing-halt |archive-date=1 October 2016 |access-date=14 June 2017 |vauthors=MacDonald G}}</ref> It has not been approved for this indication in the United States,<ref name="ShapiroOtberg2015" /><ref name="pmid27489426">{{Cite journal |vauthors=Choi GS, Kim JH, Oh SY, Park JM, Hong JS, Lee YS, Lee WS |date=August 2016 |title=Safety and Tolerability of the Dual 5-Alpha Reductase Inhibitor Dutasteride in the Treatment of Androgenetic Alopecia |journal=Annals of Dermatology |volume=28 |issue=4 |pages=444–450 |doi=10.5021/ad.2016.28.4.444 |pmc=4969473 |pmid=27489426}}</ref> though it is often used ].<ref name="pmid24017975">{{Cite journal |vauthors=Nusbaum AG, Rose PT, Nusbaum BP |date=August 2013 |title=Nonsurgical therapy for hair loss |journal=Facial Plastic Surgery Clinics of North America |volume=21 |issue=3 |pages=335–342 |doi=10.1016/j.fsc.2013.04.003 |pmid=24017975}}</ref>

==Society and culture==
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===Generic names===
Dutasteride is the ] of the drug Avodart and its ], ], ], and ].<ref name="Drugs.com-2">{{Cite web |title=Dutasteride |url=https://www.drugs.com/international/dutasteride.html |url-status=live |archive-url=https://web.archive.org/web/20171211105304/https://www.drugs.com/international/dutasteride.html |archive-date=2017-12-11 |access-date=2017-12-11 |website=Drugs.com}}</ref>

===Brand names===
Dutasteride is sold primarily under the brand name Avodart, but also ] under the brand names Combodart, Duodart, and Jalyn.<ref name="Drugs.com-2" /> Dutasteride is also available in India in combination with ] under the brand names Alfusin-D and Dutalfa.<ref name="Drugs.com-2" />

===Availability===
Dutasteride is available widely throughout the world, including in the United States, Canada, the United Kingdom, Ireland, Europe, Australia, South Africa, Latin America, Asia, and elsewhere.<ref name="Drugs.com-2" /> It is available as a generic medication in many countries, including the United States.<ref name="Drugs.com" />

== References ==
{{Reflist}}

== Further reading ==
{{refbegin}}
* {{Cite journal |vauthors=Frye SV |year=2006 |title=Discovery and clinical development of dutasteride, a potent dual 5alpha-reductase inhibitor |journal=Current Topics in Medicinal Chemistry |volume=6 |issue=5 |pages=405–421 |doi=10.2174/156802606776743101 |pmid=16719800}}
{{refend}}

{{Androgens and antiandrogens}}
{{Drugs used in benign prostatic hypertrophy}}
{{Other dermatological preparations}}
{{GlaxoSmithKline}}
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Misplaced Pages:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Dutasteride: Difference between pages Add topic