Prasterone

This article is about DHEA as a medication or supplement. For the natural hormone, see DHEA.

Prasterone
Clinical data
Trade namesIntrarosa, others
Other namesEL-10; GL-701; KYH-3102; Androst-5-en-3β-ol-17-one; 3β-Hydroxyandrost-5-en-17-one; 5,6-Didehydroepiandrosterone;[1] Dehydroisoepiandrosterone[2]
AHFS/Drugs.comMonograph
MedlinePlusa617012
License data
Pregnancy
category
Routes of
administration		By mouth, vaginal (rectal), intramuscular (as prasterone enanthate), injection (as prasterone sodium sulfate)
Drug classAndrogen; Anabolic steroid; Estrogen; Neurosteroid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability50%[9]
MetabolismLiver[9]
Metabolites• Androsterone[9]
• Etiocholanolone[9]
• DHEA sulfate[9]
• Androstenedione[9]
• Androstenediol[9]
• Testosterone[9]
• Dihydrotestosterone
• Androstanediol[9]
• Estrone
• Estradiol
Elimination half-lifeDHEA: 25 minutes[10]
DHEA-S: 11 hours[10]
ExcretionUrine
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H28O2
Molar mass288.431 g·mol−1
3D model (JSmol)
Melting point148.5 °C (299.3 °F)
  • 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=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 checkY
  • Key:FMGSKLZLMKYGDP-USOAJAOKSA-N checkY
  (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]

  1. ^ Devillers J (27 April 2009). Endocrine Disruption Modeling. CRC Press. pp. 339–. ISBN 978-1-4200-7636-3.
  2. ^ Cite error: The named reference Elks-2014 was invoked but never defined (see the help page).
  3. ^ "Intrarosa". Therapeutic Goods Administration (TGA). 26 June 2023. Retrieved 10 September 2023.
  4. ^ "Intrarosa (Theramex Australia Pty Ltd)". Therapeutic Goods Administration (TGA). 28 July 2023. Retrieved 10 September 2023.
  5. ^ https://www.tga.gov.au/resources/auspar/auspar-intrarosa [bare URL]
  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.
  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.
  8. ^ "Intrarosa- prasterone insert". DailyMed. 22 November 2021. Archived from the original on 31 May 2022. Retrieved 29 May 2022.
  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.
  10. ^ 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.
  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.
  12. ^ 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.