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
651-48-9 YesY
Abbreviations DHEAS
ChemSpider 12074 N
Jmol 3D model Interactive image
PubChem 12594
  • 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 N
    Key: CZWCKYRVOZZJNM-USOAJAOKSA-N 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
  • 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
C19H28O5S
Molar mass 368.49 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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 DHEAS 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

References

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  6. ↑ 6.0 6.1 Dehydroepiandrosterone Sulfate (DHEA-S), Serum at Mayo Foundation For Medical Education And Research. Retrieved July 2012
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