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MedKoo Cat#: 562506 | Name: Pregnenolone sulfate sodium
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pregnenolone sulfate sodium is a highly potent neurosteroid. It acts by enhancing intracellular Ca2+ upon NMDA receptor-mediated synaptic activity.

Chemical Structure

Pregnenolone sulfate sodium
CAS#1852-38-6

Theoretical Analysis

MedKoo Cat#: 562506

Name: Pregnenolone sulfate sodium

CAS#: 1852-38-6

Chemical Formula: C21H31NaO5S

Exact Mass: 418.1790

Molecular Weight: 418.52

Elemental Analysis: C, 60.27; H, 7.47; Na, 5.49; O, 19.11; S, 7.66

Price and Availability

Size Price Availability Quantity
50mg USD 350.00
100mg USD 475.00
250mg USD 750.00
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Synonym
Pregnenolone sulfate sodium; Pregnenolone sulfate sodium salt;
IUPAC/Chemical Name
sodium (3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl sulfate
InChi Key
QQVJEIZJHDPTSH-UTNKIXDHSA-M
InChi Code
InChI=1S/C21H32O5S.Na/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);/q;+1/p-1/t15-,16-,17+,18-,19-,20-,21+;/m0./s1
SMILES Code
C[C@@]12[C@@H](CC[C@@H]2C(C)=O)[C@@H]3CC=C4C[C@@H](OS(=O)(O[Na])=O)CC[C@]4(C)[C@H]3CC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pregnenolone monosulfate sodium (3β-Hydroxy-5-pregnen-20-one monosulfate sodium) is a powerful neurosteroid.
In vitro activity:
As shown in the Figures 5A, B, the early activation of ERK MAPK as determined by the phosphorylation of ERK in response to RANLK was significantly attenuated following treatment with Preg (Pregnenolone). The activation phosphorylation of the other MAPK members, p38, and JNK was not affected by Preg treatment (Figures 5A, C, D). The timely and coordinated activation of NF-κB and MAPK is necessary for the subsequent induction of c-Fos and NFATc1. NFATc1 is a crucial transcription factor required for precursor cell fusion and terminal osteoclast differentiation by transcriptionally regulating the expression of numerous osteoclast genes. The expression of c-Fos and NFATc1 was induced 72 h after RANKL stimulation, but was drastically reduced when cells were cultured in the presence of Preg in a dose-dependent manner (Figures 5G–I). Together biochemical analyses suggest that Preg inhibits osteoclast formation in part by suppressing intracellular ROS production and attenuating RANKL-induced activation of ERK MAPK and NF-κB signaling cascades which subsequent reduced the effective downstream induction of Fos and NFATc1. Reference: Front Pharmacol. 2020; 11: 360. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7135856/
In vivo activity:
To assess this, PREG (Pregnenolone) (6 mg/kg s.c. once daily for 9 days, from PND 15 to 23) was administered to VEH or PCE offspring, and acute VTA-containing slices were prepared 1 and 2 days following the last administration (Fig. 6a), when PREG is cleared from the brain. Remarkably, PREG rescued LTD at excitatory synapses on dopamine neurons to CTRL levels (Fig. 6b), without affecting synaptic efficacy in CTRL offspring. Moreover, PREG ameliorated PCE-induced dopamine neuron excitability in PCE slices, measured by resting membrane potential (Fig. 6c), as well as spontaneous (Fig. 6d–f) and evoked firing activity (Fig. 6g,,h).h). PREG also fully restored the alterations in synaptic properties imposed by PCE on excitatory and inhibitory inputs on dopamine cells (Supplementary Fig. 12). Most importantly, PREG selectively prevented larger acute THC-induced enhancement of dopamine levels in NAcS (Fig. 6i,,j),j), and THC-induced disruption of somatosensory gating functions in PCE offspring (Fig. 6k). Finally, PREG mechanism of action was dissociated from its downstream neurosteroid metabolites (Supplementary Fig.13). Collectively, these results indicate that PREG prevents PCE-induced hyperdopaminergic states and confers resilience towards heightened acute effects of THC in PCE animals. Reference: Nat Neurosci. 2019 Dec; 22(12): 1975–1985. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6884689/
Solvent mg/mL mM comments
Solubility
DMSO:PBS (pH 7.2) (1:1) 0.5 1.20
Ethanol 2.0 4.78
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 418.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Sun X, Zhang C, Guo H, Chen J, Tao Y, Wang F, Lin X, Liu Q, Su L, Qin A. Pregnenolone Inhibits Osteoclast Differentiation and Protects Against Lipopolysaccharide-Induced Inflammatory Bone Destruction and Ovariectomy-Induced Bone Loss. Front Pharmacol. 2020 Mar 27;11:360. doi: 10.3389/fphar.2020.00360. PMID: 32292342; PMCID: PMC7135856. 2. Murugan S, Jakka P, Namani S, Mujumdar V, Radhakrishnan G. The neurosteroid pregnenolone promotes degradation of key proteins in the innate immune signaling to suppress inflammation. J Biol Chem. 2019 Mar 22;294(12):4596-4607. doi: 10.1074/jbc.RA118.005543. Epub 2019 Jan 15. PMID: 30647133; PMCID: PMC6433066. 3. Frau R, Miczán V, Traccis F, Aroni S, Pongor CI, Saba P, Serra V, Sagheddu C, Fanni S, Congiu M, Devoto P, Cheer JF, Katona I, Melis M. Prenatal THC exposure produces a hyperdopaminergic phenotype rescued by pregnenolone. Nat Neurosci. 2019 Dec;22(12):1975-1985. doi: 10.1038/s41593-019-0512-2. Epub 2019 Oct 14. PMID: 31611707; PMCID: PMC6884689. 4. Busquets-Garcia A, Soria-Gómez E, Redon B, Mackenbach Y, Vallée M, Chaouloff F, Varilh M, Ferreira G, Piazza PV, Marsicano G. Pregnenolone blocks cannabinoid-induced acute psychotic-like states in mice. Mol Psychiatry. 2017 Nov;22(11):1594-1603. doi: 10.1038/mp.2017.4. Epub 2017 Feb 21. PMID: 28220044; PMCID: PMC5447368.
In vitro protocol:
1. Sun X, Zhang C, Guo H, Chen J, Tao Y, Wang F, Lin X, Liu Q, Su L, Qin A. Pregnenolone Inhibits Osteoclast Differentiation and Protects Against Lipopolysaccharide-Induced Inflammatory Bone Destruction and Ovariectomy-Induced Bone Loss. Front Pharmacol. 2020 Mar 27;11:360. doi: 10.3389/fphar.2020.00360. PMID: 32292342; PMCID: PMC7135856. 2. Murugan S, Jakka P, Namani S, Mujumdar V, Radhakrishnan G. The neurosteroid pregnenolone promotes degradation of key proteins in the innate immune signaling to suppress inflammation. J Biol Chem. 2019 Mar 22;294(12):4596-4607. doi: 10.1074/jbc.RA118.005543. Epub 2019 Jan 15. PMID: 30647133; PMCID: PMC6433066.
In vivo protocol:
1. Frau R, Miczán V, Traccis F, Aroni S, Pongor CI, Saba P, Serra V, Sagheddu C, Fanni S, Congiu M, Devoto P, Cheer JF, Katona I, Melis M. Prenatal THC exposure produces a hyperdopaminergic phenotype rescued by pregnenolone. Nat Neurosci. 2019 Dec;22(12):1975-1985. doi: 10.1038/s41593-019-0512-2. Epub 2019 Oct 14. PMID: 31611707; PMCID: PMC6884689. 2. Busquets-Garcia A, Soria-Gómez E, Redon B, Mackenbach Y, Vallée M, Chaouloff F, Varilh M, Ferreira G, Piazza PV, Marsicano G. Pregnenolone blocks cannabinoid-induced acute psychotic-like states in mice. Mol Psychiatry. 2017 Nov;22(11):1594-1603. doi: 10.1038/mp.2017.4. Epub 2017 Feb 21. PMID: 28220044; PMCID: PMC5447368.
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Expression, sorting and transport studies for the orphan carrier SLC10A4 in neuronal and non-neuronal cell lines and in Xenopus laevis oocytes. BMC Neurosci. 2015 Jun 19;16:35. doi: 10.1186/s12868-015-0174-2. PubMed PMID: 26084360; PubMed Central PMCID: PMC4472396. 5: Grosser G, Fietz D, Günther S, Bakhaus K, Schweigmann H, Ugele B, Brehm R, Petzinger E, Bergmann M, Geyer J. Cloning and functional characterization of the mouse sodium-dependent organic anion transporter Soat (Slc10a6). J Steroid Biochem Mol Biol. 2013 Nov;138:90-9. doi: 10.1016/j.jsbmb.2013.03.009. Epub 2013 Apr 3. PubMed PMID: 23562556. 6: Horishita T, Ueno S, Yanagihara N, Sudo Y, Uezono Y, Okura D, Sata T. Inhibition by pregnenolone sulphate, a metabolite of the neurosteroid pregnenolone, of voltage-gated sodium channels expressed in Xenopus oocytes. J Pharmacol Sci. 2012;120(1):54-8. Epub 2012 Aug 8. PubMed PMID: 22878600. 7: Lee KH, Cho JH, Choi IS, Park HM, Lee MG, Choi BJ, Jang IS. Pregnenolone sulfate enhances spontaneous glutamate release by inducing presynaptic Ca2+-induced Ca2+ release. Neuroscience. 2010 Nov 24;171(1):106-16. doi: 10.1016/j.neuroscience.2010.07.057. Epub 2010 Sep 17. PubMed PMID: 20816925. 8: Geyer J, Fernandes CF, Döring B, Burger S, Godoy JR, Rafalzik S, Hübschle T, Gerstberger R, Petzinger E. Cloning and molecular characterization of the orphan carrier protein Slc10a4: expression in cholinergic neurons of the rat central nervous system. Neuroscience. 2008 Apr 9;152(4):990-1005. doi: 10.1016/j.neuroscience.2008.01.049. Epub 2008 Feb 8. PubMed PMID: 18355966. 9: Kohjitani A, Fuda H, Hanyu O, Strott CA. Regulation of SULT2B1a (pregnenolone sulfotransferase) expression in rat C6 glioma cells: relevance of AMPA receptor-mediated NO signaling. Neurosci Lett. 2008 Jan 3;430(1):75-80. Epub 2007 Oct 30. PubMed PMID: 18054434. 10: Geyer J, Döring B, Meerkamp K, Ugele B, Bakhiya N, Fernandes CF, Godoy JR, Glatt H, Petzinger E. Cloning and functional characterization of human sodium-dependent organic anion transporter (SLC10A6). J Biol Chem. 2007 Jul 6;282(27):19728-41. Epub 2007 May 9. PubMed PMID: 17491011. 11: Mameli M, Carta M, Partridge LD, Valenzuela CF. Neurosteroid-induced plasticity of immature synapses via retrograde modulation of presynaptic NMDA receptors. J Neurosci. 2005 Mar 2;25(9):2285-94. PubMed PMID: 15745954. 12: Kudo K, Tachikawa E, Kashimoto T. Inhibition by pregnenolone sulfate of nicotinic acetylcholine response in adrenal chromaffin cells. Eur J Pharmacol. 2002 Dec 5;456(1-3):19-27. PubMed PMID: 12450565. 13: St-Pierre MV, Hagenbuch B, Ugele B, Meier PJ, Stallmach T. Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta. J Clin Endocrinol Metab. 2002 Apr;87(4):1856-63. PubMed PMID: 11932330. 14: Tallova J, Tomandl J, Bicikova M, Simickova M. Homocysteine in breast cyst fluid. Eur J Clin Invest. 2001 Jul;31(7):623-7. PubMed PMID: 11454018. 15: Barbosa AD, Morato GS. Effect of epipregnanolone and pregnenolone sulfate on chronic tolerance to ethanol. Pharmacol Biochem Behav. 2000 Nov;67(3):459-64. PubMed PMID: 11164072. 16: Tan E, Tirona RG, Pang KS. Lack of zonal uptake of estrone sulfate in enriched periportal and perivenous isolated rat hepatocytes. Drug Metab Dispos. 1999 Mar;27(3):336-41. PubMed PMID: 10064563. 17: Yamamoto T, Yamanaka T, Miyahara H, Matsunaga T. The neurosteroid pregnenolone sulfate excites medial vestibular nucleus neurons. Acta Otolaryngol Suppl. 1998;533:22-5. PubMed PMID: 9657306. 18: Purohit A, Williams GJ, Howarth NM, Potter BV, Reed MJ. Inactivation of steroid sulfatase by an active site-directed inhibitor, estrone-3-O-sulfamate. Biochemistry. 1995 Sep 12;34(36):11508-14. PubMed PMID: 7547880. 19: Kavaliers M, Kinsella DM. Male preference for the odors of estrous female mice is reduced by the neurosteroid pregnenolone sulfate. Brain Res. 1995 Jun 5;682(1-2):222-6. PubMed PMID: 7552317. 20: Tan HL, Tang LWT, Chin SY, Chan ECY. Investigation of the arcane inhibition of human organic anion transporter 3 by benzofuran antiarrhythmic agents. Drug Metab Pharmacokinet. 2021 Jun;38:100390. doi: 10.1016/j.dmpk.2021.100390. Epub 2021 Mar 20. PMID: 33836300.