Prasterone

Prasterone
Clinical data
Trade names	Intrarosa, others
Other names	EL-10; GL-701; KYH-3102; Androst-5-en-3β-ol-17-one; 3β-Hydroxyandrost-5-en-17-one; 5,6-Didehydroepiandrosterone; Dehydroisoepiandrosterone
AHFS/Drugs.com	Monograph
MedlinePlus	a617012
License data	US DailyMed: Prasterone;
Pregnancy; category	AU: D; ;
Routes of; administration	By mouth, vaginal (rectal), intramuscular (as prasterone enanthate), injection (as prasterone sodium sulfate)
Drug class	Androgen; Anabolic steroid; Estrogen; Neurosteroid
ATC code	G03XX01 (WHO) ; G03EA03 (WHO) (combination with estrogen); QA14AA07 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	50%
Metabolism	Liver
Metabolites	• Androsterone; • Etiocholanolone; • DHEA sulfate; • Androstenedione; • Androstenediol; • Testosterone; • Dihydrotestosterone; • Androstanediol; • Estrone; • Estradiol
Elimination half-life	DHEA: 25 minutes; DHEA-S: 11 hours
Excretion	Urine
Identifiers
	IUPAC name (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one;
CAS Number	53-43-0 ;
PubChem CID	5881;
IUPHAR/BPS	2370;
DrugBank	DB01708 ;
ChemSpider	5670 ;
UNII	459AG36T1B;
KEGG	D08409;
ChEBI	CHEBI:28689 ;
ChEMBL	ChEMBL90593 ;
Chemical and physical data
Formula	C19H28O2
Molar mass	288.431 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	148.5 °C (299.3 °F)
	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;
	InChI InChI=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 ; Key:FMGSKLZLMKYGDP-USOAJAOKSA-N ;
	(verify)

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 old age, as a component of menopausal hormone therapy, to treat painful sexual intercourse due to vaginal atrophy, and to prepare the cervix for childbirth, among other uses.^[9]^[11] It is taken by mouth, by application to the skin, in through the vagina, or by injection into muscle.^[11]

Side effects of prasterone in women include symptoms of masculinization like oily skin, acne, increased hair growth, voice changes, and increased sexual desire, headaches, insomnia, and others.^[9]^[11] The compound is a naturally occurring prohormone of androgens and estrogens and hence is an agonist of the androgen and estrogen receptors, the respective biological targets of androgens like testosterone and estrogens like estradiol.^[9]^[12] Prasterone also has a variety of activities of its own, including neurosteroid and other activities.^[12]

DHEA, the active ingredient of prasterone, was discovered in 1934.^[9]^[11] An association between DHEA levels and aging was first reported in 1965.^[9]^[11] The compound started being used as a medication in the late 1970s and as a supplement in the early 1980s.^[9]^[11] The marketing of prasterone over-the-counter as a supplement is allowed in the United States but is banned in many other countries.^[9]

^ Devillers J (27 April 2009). Endocrine Disruption Modeling. CRC Press. pp. 339–. ISBN 978-1-4200-7636-3.
^ Cite error: The named reference Elks-2014 was invoked but never defined (see the help page).
^ "Intrarosa". Therapeutic Goods Administration (TGA). 26 June 2023. Retrieved 10 September 2023.
^ "Intrarosa (Theramex Australia Pty Ltd)". Therapeutic Goods Administration (TGA). 28 July 2023. Retrieved 10 September 2023.
^ https://www.tga.gov.au/resources/auspar/auspar-intrarosa
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
^ "Summary Basis of Decision (SBD) for Intrarosa". Health Canada. 23 October 2014. Archived from the original on 31 May 2022. Retrieved 29 May 2022.
^ "Intrarosa- prasterone insert". DailyMed. 22 November 2021. Archived from the original on 31 May 2022. Retrieved 29 May 2022.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Cupp MJ, Tracy TS (10 December 2002). Dietary Supplements: Toxicology and Clinical Pharmacology. Springer Science & Business Media. pp. 123–147. ISBN 978-1-59259-303-3. Archived from the original on 14 January 2023. Retrieved 4 March 2018.
^ ^a ^b Oddens BJ, Vermeulen A (15 November 1996). Androgens and the Aging Male. CRC Press. pp. 5–. ISBN 978-1-85070-763-9. Archived from the original on 14 January 2023. Retrieved 17 July 2017.
^ ^a ^b ^c ^d ^e ^f Rutkowski K, Sowa P, Rutkowska-Talipska J, Kuryliszyn-Moskal A, Rutkowski R (July 2014). "Dehydroepiandrosterone (DHEA): hypes and hopes". Drugs. 74 (11): 1195–1207. doi:10.1007/s40265-014-0259-8. PMID 25022952. S2CID 26554413.
^ ^a ^b Prough RA, Clark BJ, Klinge CM (April 2016). "Novel mechanisms for DHEA action". Journal of Molecular Endocrinology. 56 (3): R139–R155. doi:10.1530/JME-16-0013. PMID 26908835.

[Devillers-2009-1] Devillers J (27 April 2009). Endocrine Disruption Modeling. CRC Press. pp. 339–. ISBN 978-1-4200-7636-3.

[Elks-2014-2] Cite error: The named reference Elks-2014 was invoked but never defined (see the help page).

[Therapeutic_Goods_Administration_(TGA)-2023-3] "Intrarosa". Therapeutic Goods Administration (TGA). 26 June 2023. Retrieved 10 September 2023.

[Therapeutic_Goods_Administration_(TGA)-2023-2-4] "Intrarosa (Theramex Australia Pty Ltd)". Therapeutic Goods Administration (TGA). 28 July 2023. Retrieved 10 September 2023.

[5] ttps://www.tga.gov.au/resources/auspar/auspar-intrarosa

[Diário_Oficial_da_União-2023-6] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.

[Health_Canada-2014-7] "Summary Basis of Decision (SBD) for Intrarosa". Health Canada. 23 October 2014. Archived from the original on 31 May 2022. Retrieved 29 May 2022.

[DailyMed-2021-8] "Intrarosa- prasterone insert". DailyMed. 22 November 2021. Archived from the original on 31 May 2022. Retrieved 29 May 2022.

[Cupp-2002-9] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Cupp MJ, Tracy TS (10 December 2002). Dietary Supplements: Toxicology and Clinical Pharmacology. Springer Science & Business Media. pp. 123–147. ISBN 978-1-59259-303-3. Archived from the original on 14 January 2023. Retrieved 4 March 2018.

[Oddens-1996-10] Oddens BJ, Vermeulen A (15 November 1996). Androgens and the Aging Male. CRC Press. pp. 5–. ISBN 978-1-85070-763-9. Archived from the original on 14 January 2023. Retrieved 17 July 2017.

[pmid25022952-11] ^ ^a ^b ^c ^d ^e ^f Rutkowski K, Sowa P, Rutkowska-Talipska J, Kuryliszyn-Moskal A, Rutkowski R (July 2014). "Dehydroepiandrosterone (DHEA): hypes and hopes". Drugs. 74 (11): 1195–1207. doi:10.1007/s40265-014-0259-8. PMID 25022952. S2CID 26554413.

[pmid26908835-12] Prough RA, Clark BJ, Klinge CM (April 2016). "Novel mechanisms for DHEA action". Journal of Molecular Endocrinology. 56 (3): R139–R155. doi:10.1530/JME-16-0013. PMID 26908835.

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