DHEAS

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 Androstenolone sulfate; Prasterone sulfate; Androst-5-en-3β-ol-17-one 3β-sulfate
Identifiers
CAS Number	651-48-9^Y
3D model (JSmol)	Interactive image
Abbreviations	DHEA sulfate; DHEA-S; DHEAS
ChemSpider	12074^N
PubChem CID	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, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that is produced by the adrenal cortex. It is the 3β-sulfate ester and a metabolite of dehydroepiandrosterone (DHEA) that circulates in far greater relative concentrations. The steroid is hormonally inert and is instead an important neurosteroid and neurotrophin.

Similarly to other conjugated steroids, DHEA-S is devoid of hormonal activity, lacking affinity for the steroid hormone receptors. However, DHEA-S retains activity as a neurosteroid and neurotrophin. It has been found to act as a positive allosteric modulator of the NMDA receptor (50 nM–1 µM), negative allosteric modulator of the GABA_A and glycine receptors, and weak agonist of the sigma-1 receptor (K_d > 50 µM). In addition, DHEA-S has been found to directly bind to and activate the TrkA and p75^NTR – receptors of neurotrophins like nerve growth factor (NGF) and brain-derived neurotrophic factor (BDNF) – with high affinity (around 5 nM).