Prasteroneのソースを表示

{{Short description|Medical usage of the prasterone compound}}
{{About|DHEA as a medication or supplement|the natural hormone|DHEA}}
{{Use dmy dates|date=December 2023}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Use PMID reference names|date=December 2023}}
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 443682301
| image = Dehydroepiandrosteron.svg
| image_class = skin-invert-image
| width = 225
| alt = 
| image2 = Dehydroepiandrosterone molecule ball.png
| width2 = 235
| alt2 = 
| caption =

<!-- Clinical data -->
| pronounce = 
| tradename = Intrarosa, others
| Drugs.com = {{drugs.com|monograph|prasterone}}
| MedlinePlus = a617012
| DailyMedID = Prasterone
| pregnancy_AU = D
| pregnancy_AU_comment = <ref name="Therapeutic Goods Administration (TGA)-2023">{{cite web | title=Intrarosa | website=Therapeutic Goods Administration (TGA) | date=26 June 2023 | url=https://www.tga.gov.au/resources/auspmd/intrarosa | access-date=10 September 2023}}</ref>
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]], [[vaginal administration|vaginal]] ([[Rectal administration|rectal]]), [[intramuscular injection|intramuscular]] (as [[prasterone enanthate]]), [[injection (medicine)|injection]] (as [[prasterone sodium sulfate]])
| class = [[Androgen]]; [[Anabolic steroid]]; [[Estrogen]]; [[Neurosteroid]]
| ATC_prefix = G03
| ATC_suffix = XX01
| ATC_supplemental = <br />{{ATC|G03|EA03}} (combination with [[estrogen]])<br />{{ATCvet|A14|AA07}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = <ref name="Therapeutic Goods Administration (TGA)-2023-2">{{cite web | title=Intrarosa (Theramex Australia Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=28 July 2023 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/intrarosa-theramex-australia-pty-ltd | access-date=10 September 2023}}</ref><ref>https://www.tga.gov.au/resources/auspar/auspar-intrarosa {{Bare URL inline|date=August 2024}}</ref>
| legal_BR = C5
| legal_BR_comment = <ref name="Diário Oficial da União-2023">{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=15 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA = Schedule IV
| legal_CA_comment = <ref name="Health Canada-2014">{{cite web | title=Summary Basis of Decision (SBD) for Intrarosa | website=[[Health Canada]] | date=23 October 2014 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00466&lang=en | access-date=29 May 2022 | archive-date=31 May 2022 | archive-url=https://web.archive.org/web/20220531045451/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00466&lang=en | url-status=live }}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment = 
| legal_US = Rx-only
| legal_US_comment = <ref name="DailyMed-2021">{{cite web | title=Intrarosa- prasterone insert | website=DailyMed | date=22 November 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ada639d4-bac0-2ad0-e053-2a95a90afce7 | access-date=29 May 2022 | archive-date=31 May 2022 | archive-url=https://web.archive.org/web/20220531045451/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ada639d4-bac0-2ad0-e053-2a95a90afce7 | url-status=live }}</ref>
| legal_EU = Rx-only
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 50%<ref name="Cupp-2002" />
| protein_bound = 
| metabolism = [[Liver]]<ref name="Cupp-2002" />
| metabolites = • [[Androsterone]]<ref name="Cupp-2002" /><br />• [[Etiocholanolone]]<ref name="Cupp-2002" /><br />• [[Dehydroepiandrosterone sulfate|{{abbr|DHEA|Dehydroepiandrosterone}} sulfate]]<ref name="Cupp-2002" /><br />• [[Androstenedione]]<ref name="Cupp-2002" /><br />• [[Androstenediol]]<ref name="Cupp-2002" /><br />• [[Testosterone]]<ref name="Cupp-2002" /><br />• [[Dihydrotestosterone]]<br />• [[Androstanediol]]<ref name="Cupp-2002" /><br />• [[Estrone]]<br />• [[Estradiol]]
| onset = 
| elimination_half-life = {{abbr|DHEA|Dehydroepiandrosterone}}: 25&nbsp;minutes<ref name="Oddens-1996">{{cite book|vauthors=Oddens BJ, Vermeulen A|title=Androgens and the Aging Male|url=https://books.google.com/books?id=efEnI1VdmtsC&pg=PA5|date=15 November 1996|publisher=CRC Press|isbn=978-1-85070-763-9|pages=5–|access-date=17 July 2017|archive-date=14 January 2023|archive-url=https://web.archive.org/web/20230114013439/https://books.google.com/books?id=efEnI1VdmtsC&pg=PA5|url-status=live}}</ref><br />{{abbr|DHEA-S|Dehydroepiandrosterone sulfate}}: 11&nbsp;hours<ref name="Oddens-1996" />
| duration_of_action = 
| excretion = [[Urine]]

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 53-43-0
| CAS_supplemental = 
| PubChem = 5881
| IUPHAR_ligand = 2370
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01708
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5670
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 459AG36T1B
| KEGG = D08409
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28689
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 90593
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = EL-10; GL-701; KYH-3102; Androst-5-en-3β-ol-17-one; 3β-Hydroxyandrost-5-en-17-one; 5,6-Didehydroepiandrosterone;<ref name="Devillers-2009">{{cite book| vauthors = Devillers J |title=Endocrine Disruption Modeling|url=https://books.google.com/books?id=bWHMBQAAQBAJ&pg=PA339|date=27 April 2009|publisher=CRC Press|isbn=978-1-4200-7636-3|pages=339–}}</ref> Dehydroisoepiandrosterone<ref name="Elks-2014" />

<!-- Chemical and physical data -->
| IUPAC_name = (3''S'',8''R'',9''S'',10''R'',13''S'',14''S'')-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[''a'']phenanthren-17-one
| C=19 | H=28 | O=2
| SMILES = O=C3[C@]2(CC[C@@H]1[C@@]4(C(=C/C[C@H]1[C@@H]2CC3)\C[C@@H](O)CC4)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FMGSKLZLMKYGDP-USOAJAOKSA-N
| density = 
| density_notes = 
| melting_point = 148.5
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}

<!-- Definition and medical uses -->
'''Prasterone''', also known as '''dehydroepiandrosterone''' ('''DHEA''') and sold under the brand name '''Intrarosa''' among others, is a [[medication]] as well as [[over-the-counter]] [[dietary supplement]] which is used to correct DHEA deficiency due to [[adrenal insufficiency]] or [[aging|old age]], as a component of [[menopausal hormone therapy]], to treat [[dyspareunia|painful sexual intercourse]] due to [[vaginal atrophy]], and to prepare the [[cervix]] for [[childbirth]], among other uses.<ref name="Cupp-2002">{{cite book|vauthors=Cupp MJ, Tracy TS |title=Dietary Supplements: Toxicology and Clinical Pharmacology|url=https://books.google.com/books?id=vuqPBAAAQBAJ&pg=PA123|date=10 December 2002 |publisher=Springer Science & Business Media|isbn=978-1-59259-303-3|pages=123–147|access-date=4 March 2018|archive-date=14 January 2023 |archive-url=https://web.archive.org/web/20230114013431/https://books.google.com/books?id=vuqPBAAAQBAJ&pg=PA123|url-status=live}}</ref><ref name="pmid25022952">{{cite journal |vauthors=Rutkowski K, Sowa P, Rutkowska-Talipska J, Kuryliszyn-Moskal A, Rutkowski R |title=Dehydroepiandrosterone (DHEA): hypes and hopes |journal=Drugs |volume=74 |issue=11 |pages=1195–1207 |date=July 2014 |pmid=25022952 |doi=10.1007/s40265-014-0259-8 |s2cid=26554413}}</ref> It is taken [[oral administration|by mouth]], [[transdermal administration|by application to the skin]], [[Intravaginal administration|in through the vagina]], or [[intramuscular injection|by injection into muscle]].<ref name="pmid25022952" />

<!-- Side effects and mechanism -->
[[Side effect]]s of prasterone in women include [[symptom]]s of [[virilization|masculinization]] like [[oily skin]], [[acne]], [[hirsutism|increased hair growth]], [[voice deepening|voice changes]], and increased [[libido|sexual desire]], [[headache]]s, [[insomnia]], and others.<ref name="Cupp-2002" /><ref name="pmid25022952" /> The compound is a [[natural product|naturally occurring]] [[prohormone]] of [[androgen]]s and [[estrogen (medication)|estrogen]]s and hence is an [[agonist]] of the [[androgen receptor|androgen]] and [[estrogen receptor]]s, the respective [[biological target]]s of androgens like [[testosterone]] and estrogens like [[estradiol]].<ref name="Cupp-2002" /><ref name="pmid26908835">{{cite journal | vauthors = Prough RA, Clark BJ, Klinge CM | title = Novel mechanisms for DHEA action | journal = Journal of Molecular Endocrinology | volume = 56 | issue = 3 | pages = R139–R155 | date = April 2016 | pmid = 26908835 | doi = 10.1530/JME-16-0013 | doi-access = free }}</ref> Prasterone also has a variety of activities of its own, including [[neurosteroid]] and other activities.<ref name="pmid26908835" />

<!-- History, society, and culture -->
[[DHEA]], the [[active ingredient]] of prasterone, was discovered in 1934.<ref name="Cupp-2002" /><ref name="pmid25022952" /> An association between DHEA levels and aging was first reported in 1965.<ref name="Cupp-2002" /><ref name="pmid25022952" /> The compound started being used as a medication in the late 1970s and as a supplement in the early 1980s.<ref name="Cupp-2002" /><ref name="pmid25022952" /> The marketing of prasterone over-the-counter as a supplement is allowed in the [[United States]] but is banned in many other countries.<ref name="Cupp-2002" />

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