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Pregnenolone sulfate

Pregnenolone sulfate
IUPAC name

[(3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate

Other names

Pregn-sulf; Pregnenolone monosulfate; Pregnenolone hydrogen sulfate; Pregnenolone 3β-sulfate; 5-Pregnen-3β-ol-20-one sulfate; (3β)-3-(Sulfooxy)pregn-5-en-20-one; 5-Pregnen-3β-sulfate-20-one; 20-Oxo-5-pregnen-3β-yl sulfate

Identifiers
CAS number  YesY
PubChem
ChEMBL  N
Jmol-3D images Image 1
Properties
Molecular formula C21H32O5S
Molar mass 396.54 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Pregnenolone sulfate (3β-hydroxypregn-5-en-20-one sulfate; abbreviated as PS) is an endogenous excitatory neurosteroid that is synthesized from pregnenolone.[1][2] It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects.[2]

Mechanism

Pregnenolone sulfate is a neurosteroid with excitatory effects in the brain, acting as a potent negative allosteric modulator of the GABAA receptor and a weak positive allosteric modulator of the NMDA receptor.[1][2] To a lesser extent, it also acts as a negative allosteric modulator of the AMPA, kainate, and glycine receptors,[3][4] and may interact with the nACh receptors as well.[1] In addition to its effects on ligand-gated ion channels, pregnenolone sulfate is an agonist of the sigma receptor,[2] as well as an activator of the TRPM1 and TRPM3 channels.[1] It may also interact with potassium channels and voltage-gated sodium channels.[1]

See also

References

  1. ^ a b c d e Harteneck C (2013). "Pregnenolone sulfate: from steroid metabolite to TRP channel ligand". Molecules 18 (10): 12012–28.  
  2. ^ a b c d Reddy DS (2010). "Neurosteroids: endogenous role in the human brain and therapeutic potentials". Prog. Brain Res. 186: 113–37.  
  3. ^ Park-Chung M, Wu FS, Farb DH (July 1994). "3 alpha-Hydroxy-5 beta-pregnan-20-one sulfate: a negative modulator of the NMDA-induced current in cultured neurons". Mol. Pharmacol. 46 (1): 146–50.  
  4. ^ Yaghoubi N, Malayev A, Russek SJ, Gibbs TT, Farb DH (August 1998). "Neurosteroid modulation of recombinant ionotropic glutamate receptors". Brain Res. 803 (1-2): 153–60.  


Precursors
Corticosteroids
Sex steroids
Neurosteroids
Others
Receptor
(ligands)

Note: See for a full list of GABAA PAMs.

Transporter
(blockers)
GAT
Enzyme
(inhibitors)
GAD
Others
Receptor
Ligands
Unknown
interaction


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