Dehydroepiandrosterone sulfate

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Dehydroepiandrosterone sulfate
DHEA sulfate.png
Sulfato de dehidroepiandrosterona3D.png
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
3D model (Jmol)
Abbreviations DHEAS
ChemSpider
Properties
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 (DHEA-S), also known as prasterone sulfate, is a naturally occurring, endogenous androstane steroid and neurosteroid and the 3β-sulfate ester of dehydroepiandrosterone (DHEA).

As the sodium salt, prasterone sodium sulfate, DHEA-S is used as a pharmaceutical drug in Japan in the treatment of insufficient cervical ripening and cervical dilation during childbirth.[1][2][3][4][5][6][7]

Synthesis[edit]

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.[8] 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[edit]

Dehydroepiandrosterone sulfate levels above 1890 micromol/L or 700-800 µg/dL are highly suggestive of adrenal dysfunction because DHEA-S is made by the adrenal glands[9][10] and also synthesized in brain[11]. The presence of DHEA-S is therefore used to rule out ovarian or testicular origin of excess androgen.

Therapeutic use[edit]

The Endocrine Society recommends against the therapeutic use of DHEA sulfate in both healthy women and those with adrenal insufficiency, as its role is not clear from studies performed so far.[12] 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.[12]

In otherwise elderly women, in whom an age-related fall of DHEA sulfate may be associated with menopausal symptoms and reduced libido, DHEA sulfate supplementation cannot currently be said to improve outcomes.[13]

Reference ranges[edit]

Reference ranges for dehydroepiandrosterone sulfate in females[14]
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[14]
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[edit]

References[edit]

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–. ISBN 978-1-4757-2085-3. 
  2. ^ John W. Blunt; Murray H. G. Munro (19 September 2007). Dictionary of Marine Natural Products with CD-ROM. CRC Press. pp. 1075–. ISBN 978-0-8493-8217-8. 
  3. ^ A. Kleemann; J. Engel; B. Kutscher; D. Reichert (14 May 2014). Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs. Thieme. pp. 2441–2442. ISBN 978-3-13-179525-0. 
  4. ^ Martin Negwer; Hans-Georg Scharnow (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1831. ISBN 978-3-527-30247-5. 3β-Hydroxyandrost-5-en-17-one hydrogen sulfate = (3β)-3-(Sulfooxy)androst-5-en-17-one. R: Sodium salt (1099-87-2). S: Astenile, Dehydroepiandrosterone sulfate sodium, DHA-S, DHEAS, KYH 3102, Mylis, PB 005, Prasterone sodium sulfate, Teloin 
  5. ^ Jianqiu, Y. (1992). Clinical Application of Prasterone Sodium Sulfate. Chinese Journal of New Drugs, 5, 015.
  6. ^ Sakaguchi M, Sakai T, Adachi Y, Kawashima T, Awata N (1992). "The biological fate of sodium prasterone sulfate after vaginal administration. I. Absorption and excretion in rats". J. Pharmacobio-dyn. 15 (2): 67–73. PMID 1403604. 
  7. ^ Sakai, T., Sakaguchi, M., Adachi, Y., Kawashima, T., & Awata, N. (1992). The Biological Fate of Sodium Prasterone Sulfate after Vaginal Administration II: Distribution after Single and Multiple Administration to Pregnant Rats. 薬物動態, 7(1), 87-101.
  8. ^ 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 2699571Freely accessible. PMID 17945481. 
  9. ^ 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. 
  10. ^ "Polycystic Ovarian Syndrome Workup". eMedicine. 25 October 2011. Retrieved 19 November 2011. 
  11. ^ Vaudry H, Do Rego J-L, Burel D, et al. Neurosteroid Biosynthesis in the Brain of Amphibians. Frontiers in Endocrinology. 2011;2:79. doi:10.3389/fendo.2011.00079.
  12. ^ a b 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. 
  13. ^ 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. 
  14. ^ a b Dehydroepiandrosterone Sulfate (DHEA-S), Serum at Mayo Foundation For Medical Education And Research. Retrieved July 2012