:Pregnenolone sulfate
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 377858355
| ImageFile = Pregnenolone sulfate.svg
| ImageSize = 240
| ImageAlt = Skeletal formula
| ImageFile1 = Pregnenolone sulfate anion ball.png
| ImageSize1 = 230
| ImageAlt1 = Ball-and-stick model of pregnenolone sulfate as an anion
| IUPACName = 20-Oxopregn-5-en-3β-yl hydrogen sulfate
| SystematicName = (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
| OtherNames = 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
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4290
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 1247-64-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 04Y4D91RG0
| PubChem = 105074
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 141573
| 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
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 94802
| 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
| InChIKey = DIJBBUIOWGGQOP-QGVNFLHTBX
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DIJBBUIOWGGQOP-QGVNFLHTSA-N
}}
|Section2={{Chembox Properties
| C=21 | H=32 | O=5 | S=1
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|Section3={{Chembox Hazards
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Pregnenolone sulfate (PS, PREGS) is an endogenous excitatory neurosteroid that is synthesized from pregnenolone.{{cite journal | author = Harteneck C | title = Pregnenolone sulfate: from steroid metabolite to TRP channel ligand | journal = Molecules | volume = 18 | issue = 10 | pages = 12012–28 | year = 2013 | pmid = 24084011 | doi = 10.3390/molecules181012012|pmc=6270300 | doi-access = free }}{{cite journal | author = Reddy DS | title = Neurosteroids: endogenous role in the human brain and therapeutic potentials | journal = Prog. Brain Res. | volume = 186 | pages = 113–37 | year = 2010 | pmid = 21094889 | pmc = 3139029 | doi = 10.1016/B978-0-444-53630-3.00008-7 }} It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects.
Biological activity
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. To a lesser extent, it also acts as a negative allosteric modulator of the AMPA, kainate, and glycine receptors,{{cite journal |vauthors=Park-Chung M, Wu FS, Farb DH | title = 3 alpha-Hydroxy-5 beta-pregnan-20-one sulfate: a negative modulator of the NMDA-induced current in cultured neurons | journal = Mol. Pharmacol. | volume = 46 | issue = 1 | pages = 146–50 |date=July 1994 | pmid = 7520124 }}{{cite journal |vauthors=Yaghoubi N, Malayev A, Russek SJ, Gibbs TT, Farb DH | title = Neurosteroid modulation of recombinant ionotropic glutamate receptors | journal = Brain Res. | volume = 803 | issue = 1–2 | pages = 153–60 |date=August 1998 | pmid = 9729352 | doi = 10.1016/s0006-8993(98)00644-1| doi-access = free }} and may interact with the nACh receptors as well. In addition to its effects on ligand-gated ion channels, pregnenolone sulfate is an agonist of the sigma receptor, as well as an activator of the TRPM1 and TRPM3 channels. It may also interact with potassium channels and voltage-gated sodium channels and has been found to inhibit voltage-gated calcium channels.{{cite journal | vauthors = Mellon SH | title = Neurosteroid regulation of central nervous system development | journal = Pharmacol. Ther. | volume = 116 | issue = 1 | pages = 107–24 | year = 2007 | pmid = 17651807 | pmc = 2386997 | doi = 10.1016/j.pharmthera.2007.04.011 }}
Biochemistry
File:Steroidogenesis.svg, 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 naturally occurring pregnane steroid and 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
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{{Steroid hormones}}
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{{GABA receptor modulators}}
{{Glycine receptor modulators}}
{{Ionotropic glutamate receptor modulators}}
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{{Transient receptor potential channel modulators}}
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Category:AMPA receptor antagonists
Category:GABAA receptor negative allosteric modulators
Category:Glycine receptor antagonists
Category:Kainate receptor antagonists