Dehydroepiandrosterone sulfate

Dehydroepiandrosterone sulfate

Names
IUPAC name [(3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Other names Prasterone sulfate
Identifiers
CAS Number	651-48-9
3D model (Jmol)	Interactive image
Abbreviations	DHEAS
ChemSpider	12074
PubChem	12594
InChI InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1 Key: CZWCKYRVOZZJNM-USOAJAOKSA-N InChI=1/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1 Key: CZWCKYRVOZZJNM-USOAJAOKBK
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C
Properties
Chemical formula	C19H28O5S
Molar mass	368.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dehydroepiandrosterone sulfate or DHEA-S is a metabolite of dehydroepiandrosterone (DHEA).

Synthesis

Dehydroepiandrosterone sulfate is produced by the addition of a sulfate group, catalyzed by the sulfotransferase enzymes SULT1A1 and SULT1E1, which also produce estrone sulfate from estrone. DHEA sulfate can also be back-converted to DHEA through the action of steroid sulfatase.

In the zona reticularis layer of the adrenal cortex, DHEA-sulfate is generated by SULT2A1.^[1] This layer of the adrenal cortex is thought to be the primary source of serum DHEA-sulfate. DHEA sulfate levels decline as a person ages as the reticularis layer diminishes in size.

Use as biomarker

Dehydroepiandrosterone sulfate levels above 1890 micromol/L or 700-800 µg/dL are highly suggestive of adrenal dysfunction because DHEA-S is made exclusively by the adrenal glands.^[2][3] Presence of DHEA-S is therefore used to rule out ovarian or testicular origin of excess androgen.

Therapeutic use

The Endocrine Society recommends against the therapeutic use of DHEA sulfate in both healthy women and those with adrenal insufficiency, as their role is not clear from studies performed so far.^[4] The routine use of DHEA-S and other androgens is discouraged in the treatment of women with low androgen levels due to hypopituitarism, adrenal insufficiency, menopause due to ovarian surgery, glucocorticoid use, or other conditions associated with low androgen levels; this is because there are limited data supporting improvement in signs and symptoms with therapy and no long-term studies of risk.^[4]

In otherwise elderly women, in whom an age-related fall DHEA sulfate may be associated with menopausal symptoms and reduced libido, DHEA sulfate supplementation cannot currently be said to improve outcomes.^[5]

Reference ranges

Reference ranges for dehydroepiandrosterone sulfate in females^[6]

Tanner stage and average age		Lower limit	Upper limit	Unit
Tanner stage I	>14 days	16	96	µg/dL
Tanner stage II	10.5 years	22	184
Tanner stage III	11.6 years	<15	296
Tanner stage IV	12.3 years	17	343
Tanner stage V	14.5 years	44	332
18–29 years		44	332
30–39 years		31	228
40–49 years		18	244
50–59 years		<15	200
> or =60 years		<15	157

Reference ranges for dehydroepiandrosterone sulfate in males^[6]

Tanner stage and average age		Lower limit	Upper limit	Unit
Tanner stage I	>14 days	<15	120	µg/dL
Tanner stage II	11.5 years	<15	333
Tanner stage III	13.6 years	<15	312
Tanner stage IV	15.1 years	29	412
Tanner stage V	18.0 years	89	457
18–29 years		89	457
30–39 years		65	334
40–49 years		48	244
50–59 years		35	179
> or =60 years		25	131

See also

• Polycystic ovary syndrome

References

1. Rainey WE, Nakamura Y (February 2008). "Regulation of the adrenal androgen biosynthesis". J. Steroid Biochem. Mol. Biol. 108 (3-5): 281–86. doi:10.1016/j.jsbmb.2007.09.015. PMC 2699571. PMID 17945481.
2. Somani N, Harrison S, Bergfeld WF (2008). "The clinical evaluation of hirsutism". Dermatologic therapy. 21 (5): 376–91. doi:10.1111/j.1529-8019.2008.00219.x. PMID 18844715.
3. "Polycystic Ovarian Syndrome Workup". eMedicine. 25 October 2011. Retrieved 19 November 2011.
4. Wierman, Margaret E.; Arlt, Wiebke; Basson, Rosemary; Davis, Susan R.; Miller, Karen K.; Murad, Mohammad H.; Rosner, William; Santoro, Nanette. "Androgen Therapy in Women: A Reappraisal: An Endocrine Society Clinical Practice Guideline". The Journal of Clinical Endocrinology & Metabolism. 99 (10): 3489–510. doi:10.1210/jc.2014-2260. PMID 25279570.
5. Elraiyah, Tarig; Sonbol, Mohamad Bassam; Wang, Zhen; Khairalseed, Tagwa; Asi, Noor; Undavalli, Chaitanya; Nabhan, Mohammad; Altayar, Osama; Prokop, Larry; Montori, Victor M.; Murad, Mohammad Hassan. "The Benefits and Harms of Systemic Dehydroepiandrosterone (DHEA) in Postmenopausal Women With Normal Adrenal Function: A Systematic Review and Meta-analysis". The Journal of Clinical Endocrinology & Metabolism. 99 (10): 3536–42. doi:10.1210/jc.2014-2261. PMID 25279571.
6. Dehydroepiandrosterone Sulfate (DHEA-S), Serum at Mayo Foundation For Medical Education And Research. Retrieved July 2012