Pregnenolone sulfate

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Pregnenolone sulfate
Skeletal formula
Ball-and-stick model of pregnenolone sulfate as an anion
Names
IUPAC name
20-Oxopregn-5-en-3β-yl hydrogen sulfate
Systematic IUPAC name
(1S,3aS,3bS,7S,9aR,9bS,11aS)-1-Acetyl-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-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
)
ChEMBL
ChemSpider
IUPHAR/BPS
UNII
  • InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15-,16-,17+,18-,19-,20-,21+/m0/s1 ☒N
    Key: DIJBBUIOWGGQOP-QGVNFLHTSA-N ☒N
  • InChI=1/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15-,16-,17+,18-,19-,20-,21+/m0/s1
    Key: DIJBBUIOWGGQOP-QGVNFLHTBX
SMILES
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C)C
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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Pregnenolone sulfate (PS, PREGS) is an

proconvulsant effects.[2]

Biological activity

Pregnenolone sulfate is a neurosteroid with excitatory effects in the brain, acting as a potent

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]

Biochemistry

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

Biosynthesis

Pregnenolone sulfate is synthesized from pregnenolone via sulfation. Pregnenolone itself is produced from cholesterol via cholesterol side-chain cleavage enzyme.

Chemistry

See also: List of neurosteroids

Pregnenolone sulfate, also known as pregn-5-en-3β-ol-20-one 3β-sulfate, is a

derivative of cholesterol. It is the C3β sulfate ester of pregnenolone. A closely related steroid is dehydroepiandrosterone sulfate (DHEA-S), which is the C3β sulfate ester of dehydroepiandrosterone
(DHEA).

References

  1. ^
    PMID 24084011
    .
  2. ^
    PMID 21094889
    .
  3. PMID 7520124
    .
  4. PMID 9729352
    .
  5. PMID 17651807
    .