Dehydroepiandrosterone

This article is about DHEA as a hormone. For its use as a medication or supplement, see Prasterone. For other uses, see DHEA (disambiguation). For the precursor hormone of DHEA produced mainly in the adrenal cortex, DHEA sulfate or DHEA-S, see Dehydroepiandrosterone sulfate.
Dehydroepiandrosterone
Names
IUPAC name
3β-Hydroxyandrost-5-en-17-one
Systematic IUPAC name
(3aS,3bR,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
Androstenolone; Prasterone; Androst-5-en-3β-ol-17-one; 5,6-Didehydroepiandrosterone;[1] Dehydroisoepiandrosterone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.160 Edit this at Wikidata
UNII
  • 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
  • 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
Properties
C19H28O2
Molar mass 288.424 g/mol
Melting point 148.5
Pharmacology
QA14AA07 (WHO)
G03EA03 (WHO) (combination with estrogen)
By mouth, vaginal (insert), intramuscular injection (as prasterone enanthate), injection (as prasterone sodium sulfate)
Pharmacokinetics:
50%[2]
Hepatic[2]
DHEA: 25 minutes[3]
DHEA-S: 11 hours[3]
Urine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor.[4] It is one of the most abundant circulating steroids in humans.[5] DHEA is produced in the adrenal glands,[6] the gonads, and the brain.[7] It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues.[4][8][9] However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors,[10] and acting as a neurosteroid and modulator of neurotrophic factor receptors.[11]

In the United States, DHEA is sold as an over-the-counter supplement, and medication called prasterone.

  1. ^ Devillers J (27 April 2009). Endocrine Disruption Modeling. CRC Press. pp. 339–. ISBN 978-1-4200-7636-3.
  2. ^ a b Cupp MJ, Tracy TS (10 December 2002). Dietary Supplements: Toxicology and Clinical Pharmacology. Springer Science & Business Media. pp. 135–. ISBN 978-1-59259-303-3.
  3. ^ a b Oddens BJ, Vermeulen A (15 November 1996). Androgens and the Aging Male. CRC Press. pp. 5–. ISBN 978-1-85070-763-9.
  4. ^ a b Labrie F, Luu-The V, Bélanger A, Lin SX, Simard J, Pelletier G, Labrie C (November 2005). "Is dehydroepiandrosterone a hormone?". J. Endocrinol. 187 (2): 169–96. doi:10.1677/joe.1.06264. PMID 16293766.
  5. ^ William F Ganong MD, 'Review of Medical Physiology', 22nd Ed, McGraw Hill, 2005, p. 362.
  6. ^ The Merck Index, 13th Edition, 7798
  7. ^ Schulman RA, Dean C (2007). Solve It With Supplements. New York City: Rodale, Inc. p. 100. ISBN 978-1-57954-942-8. DHEA (Dehydroepiandrosterone) is a common hormone produced in the adrenal glands, the gonads, and the brain.
  8. ^ Cite error: The named reference pmid16524719 was invoked but never defined (see the help page).
  9. ^ Scott T (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. Retrieved 25 May 2012.
  10. ^ Webb SJ, Geoghegan TE, Prough RA, Michael Miller KK (2006). "The biological actions of dehydroepiandrosterone involves multiple receptors". Drug Metabolism Reviews. 38 (1–2): 89–116. doi:10.1080/03602530600569877. PMC 2423429. PMID 16684650.
  11. ^ Friess E, Schiffelholz T, Steckler T, Steiger A (December 2000). "Dehydroepiandrosterone--a neurosteroid". European Journal of Clinical Investigation. 30 (Suppl 3): 46–50. doi:10.1046/j.1365-2362.2000.0300s3046.x. PMID 11281367. S2CID 30733847.