Dehydroepiandrosterone

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; Dehydroisoepiandrosterone
Identifiers
CAS Number	53-43-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28689 ;
ChEMBL	ChEMBL90593 ;
ChemSpider	5670 ;
DrugBank	DB01708 ;
ECHA InfoCard	100.000.160
PubChem CID	5881;
UNII	459AG36T1B ;
CompTox Dashboard (EPA)	DTXSID4020379 ;
	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 ;
	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;
Properties
Chemical formula	C19H28O2
Molar mass	288.424 g/mol
Melting point	148.5
Pharmacology
ATCvet code	QA14AA07 (WHO) ; G03EA03 (WHO) (combination with estrogen)
Routes of; administration	By mouth, vaginal (insert), intramuscular injection (as prasterone enanthate), injection (as prasterone sodium sulfate)
	Pharmacokinetics:
Bioavailability	50%
Metabolism	Hepatic
Biological half-life	DHEA: 25 minutes; DHEA-S: 11 hours
Excretion	Urine
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

^ Devillers J (27 April 2009). Endocrine Disruption Modeling. CRC Press. pp. 339–. ISBN 978-1-4200-7636-3.
^ ^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.
^ ^a ^b Oddens BJ, Vermeulen A (15 November 1996). Androgens and the Aging Male. CRC Press. pp. 5–. ISBN 978-1-85070-763-9.
^ ^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.
^ William F Ganong MD, 'Review of Medical Physiology', 22nd Ed, McGraw Hill, 2005, p. 362.
^ The Merck Index, 13th Edition, 7798
^ 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.
^ Cite error: The named reference pmid16524719 was invoked but never defined (see the help page).
^ Scott T (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. Retrieved 25 May 2012.
^ 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.
^ 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.

[Devillers2009-1] Devillers J (27 April 2009). Endocrine Disruption Modeling. CRC Press. pp. 339–. ISBN 978-1-4200-7636-3.

[CuppTracy2002-2] 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.

[OddensVermeulen1996-3] Oddens BJ, Vermeulen A (15 November 1996). Androgens and the Aging Male. CRC Press. pp. 5–. ISBN 978-1-85070-763-9.

[pmid16293766-4] 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.

[pmid16524719-8] Cite error: The named reference pmid16524719 was invoked but never defined (see the help page).

[Scott1996-9] Scott T (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. Retrieved 25 May 2012.

[pmid16684650-10] 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.

[pmid11281367-11] 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.

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