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 | |
651-48-9 | |
3D model (Jmol) | Interactive image |
Abbreviations | DHEAS |
ChemSpider | 12074 |
PubChem | 12594 |
|
|
|
|
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).
|
|
verify (what is ?) | |
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]
Contents
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 exclusively by the adrenal glands.[9][10] 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.[11] 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.[11]
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.[12]
Reference ranges[edit]
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 |
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]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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
- ^ Jianqiu, Y. (1992). Clinical Application of Prasterone Sodium Sulfate. Chinese Journal of New Drugs, 5, 015.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Polycystic Ovarian Syndrome Workup". eMedicine. 25 October 2011. Retrieved 19 November 2011.
- ^ 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.
- ^ 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.
- ^ a b Dehydroepiandrosterone Sulfate (DHEA-S), Serum at Mayo Foundation For Medical Education And Research. Retrieved July 2012