Pregnenolone sulfate

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Pregnenolone sulfate
Skeletal formula
Ball-and-stick model of pregnenolone sulfate as an anion
Names
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
3D model (JSmol)
ChemSpider
Properties
C21H32O5S
Molar mass 396.54 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pregnenolone sulfate (PS, PREGS), also known as pregn-5-en-3β-ol-20-one 3β-sulfate, 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]

Biological activity[edit]

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] and has been found to inhibit voltage-gated calcium channels.[5]

Additional images[edit]

Steroidogenesis, with pregnenolone, the precursor of pregnenolone sulfate, at bottom left.

See also[edit]

References[edit]

  1. ^ a b c d e Harteneck C (2013). "Pregnenolone sulfate: from steroid metabolite to TRP channel ligand". Molecules. 18 (10): 12012–28. PMID 24084011. doi:10.3390/molecules181012012. 
  2. ^ a b c d Reddy DS (2010). "Neurosteroids: endogenous role in the human brain and therapeutic potentials". Prog. Brain Res. 186: 113–37. PMC 3139029Freely accessible. PMID 21094889. doi:10.1016/B978-0-444-53630-3.00008-7. 
  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. PMID 7520124. 
  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. PMID 9729352. doi:10.1016/s0006-8993(98)00644-1. 
  5. ^ Mellon SH (2007). "Neurosteroid regulation of central nervous system development". Pharmacol. Ther. 116 (1): 107–24. PMC 2386997Freely accessible. PMID 17651807. doi:10.1016/j.pharmthera.2007.04.011.