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^Y
3D model (Jmol)	Interactive image
Abbreviations	DHEAS
ChemSpider	12074^N
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^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
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).
N (what is ^YN ?)
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.

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. 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.

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. Presence of DHEA-S is therefore used to rule out ovarian or testicular origin of excess androgen.

...
Wikipedia