Sodium prasterone sulfate| CAS#78590-17-7 | 651-48-9 | ERβ agonist | NMDA agonist | σ1 receptor

MedKoo Cat#: 540100 | Name: Prasterone sulfate sodium hydrate

Description:

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

Prasterone is an endogenous steroid hormone that acts as an agonist at ERβ, NMDA, and σ1 receptors, a partial agonist at ERα and AR, and antagonist at GABA-A receptors. It displays a variety of biologocial activities, including enhancing working memory and cognition, inhibiting proliferation and migration of cervical cancer cells, increasing expression of various glutamate transporters to suppress seizures, and minimizing gastric acid secretion, lipid peroxidation and ulcer formation.

Chemical Structure

Prasterone sulfate sodium hydrate

CAS#78590-17-7 (sodium)

Theoretical Analysis

MedKoo Cat#: 540100

Name: Prasterone sulfate sodium hydrate

CAS#: 78590-17-7 (sodium)

Chemical Formula: C19H31NaO7S

Exact Mass:

Molecular Weight: 426.50

Elemental Analysis: C, 53.51; H, 7.33; Na, 5.39; O, 26.26; S, 7.52

Price and Availability

Related CAS #

78590-17-7 (sodium) 651-48-9 (free acid)

Synonym

5-Androsten-3β-ol-17-one sulfate sodium salt dihydrate, Prasterone sulfate sodium salt dihydrate, Sodium dehydroepiandrosterone sulfate

IUPAC/Chemical Name

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

InChi Key

NLNMKDUYGPNWAO-OXNWJOIVSA-M

InChi Code

InChI=1S/C19H28O5S.Na.2H2O/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18;;;/h3,13-16H,4-11H2,1-2H3,(H,21,22,23);;2*1H2/q;+1;;/p-1/t13-,14-,15-,16-,18-,19-;;;/m0.../s1

SMILES Code

O=C1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](OS(=O)([O-])=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C.[H]O[H].[H]O[H].[Na+]

Appearance

Solid powder

Purity

>93% (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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 426.50 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.

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

1: Labrie F, Archer D, Bouchard C, Fortier M, Cusan L, Gomez JL, Girard G, Baron M, Ayotte N, Moreau M, Dubé R, Côté I, Labrie C, Lavoie L, Gilbert L, Martel C, Balser J. Lack of influence of dyspareunia on the beneficial effect of intravaginal prasterone (dehydroepiandrosterone, DHEA) on sexual dysfunction in postmenopausal women. J Sex Med. 2014 Jul;11(7):1766-85. doi: 10.1111/jsm.12517. Epub 2014 Apr 28. PubMed PMID: 24774442. 2: Labrie F, Martel C, Bérubé R, Côté I, Labrie C, Cusan L, Gomez JL. Intravaginal prasterone (DHEA) provides local action without clinically significant changes in serum concentrations of estrogens or androgens. J Steroid Biochem Mol Biol. 2013 Nov;138:359-67. doi: 10.1016/j.jsbmb.2013.08.002. Epub 2013 Aug 14. PubMed PMID: 23954500. 3: Labrie F, Archer DF, Bouchard C, Girard G, Ayotte N, Gallagher JC, Cusan L, Baron M, Blouin F, Waldbaum AS, Koltun W, Portman DJ, Côté I, Lavoie L, Beauregard A, Labrie C, Martel C, Balser J, Moyneur É; Members of the VVA Prasterone Group. Prasterone has parallel beneficial effects on the main symptoms of vulvovaginal atrophy: 52-week open-label study. Maturitas. 2015 May;81(1):46-56. doi: 10.1016/j.maturitas.2015.02.005. Epub 2015 Feb 16. PubMed PMID: 25771041. 4: Archer DF, Labrie F, Bouchard C, Portman DJ, Koltun W, Cusan L, Labrie C, Côté I, Lavoie L, Martel C, Balser J; VVA Prasterone Group. Treatment of pain at sexual activity (dyspareunia) with intravaginal dehydroepiandrosterone (prasterone). Menopause. 2015 Sep;22(9):950-63. doi: 10.1097/GME.0000000000000428. PubMed PMID: 25734980. 5: Labrie F, Montesino M, Archer DF, Lavoie L, Beauregard A, Côté I, Martel C, Vaillancourt M, Balser J, Moyneur E; other participating Members of the Prasterone Clinical Research Group. Influence of treatment of vulvovaginal atrophy with intravaginal prasterone on the male partner. Climacteric. 2015;18(6):817-25. doi: 10.3109/13697137.2015.1077508. Epub 2015 Oct 30. PubMed PMID: 26517756. 6: Portman DJ, Labrie F, Archer DF, Bouchard C, Cusan L, Girard G, Ayotte N, Koltun W, Blouin F, Young D, Wade A, Martel C, Dubé R; other participating members of VVA Prasterone Group. Lack of effect of intravaginal dehydroepiandrosterone (DHEA, prasterone) on the endometrium in postmenopausal women. Menopause. 2015 Dec;22(12):1289-95. doi: 10.1097/GME.0000000000000470. PubMed PMID: 25968836. 7: Kocis P. Prasterone. Am J Health Syst Pharm. 2006 Nov 15;63(22):2201-10. Review. PubMed PMID: 17090740. 8: Labrie F, Archer DF, Koltun W, Vachon A, Young D, Frenette L, Portman D, Montesino M, Côté I, Parent J, Lavoie L, Beauregard A, Martel C, Vaillancourt M, Balser J, Moyneur É; VVA Prasterone Research Group. Efficacy of intravaginal dehydroepiandrosterone (DHEA) on moderate to severe dyspareunia and vaginal dryness, symptoms of vulvovaginal atrophy, and of the genitourinary syndrome of menopause. Menopause. 2016 Mar;23(3):243-56. doi: 10.1097/GME.0000000000000571. PubMed PMID: 26731686. 9: Marder W, Somers EC, Kaplan MJ, Anderson MR, Lewis EE, McCune WJ. Effects of prasterone (dehydroepiandrosterone) on markers of cardiovascular risk and bone turnover in premenopausal women with systemic lupus erythematosus: a pilot study. Lupus. 2010 Sep;19(10):1229-36. doi: 10.1177/0961203310371156. Epub 2010 Jun 8. PubMed PMID: 20530522. 10: Goodarzi MO, Carmina E, Azziz R. DHEA, DHEAS and PCOS. J Steroid Biochem Mol Biol. 2015 Jan;145:213-25. doi: 10.1016/j.jsbmb.2014.06.003. Epub 2014 Jul 5. Review. PubMed PMID: 25008465. 11: Montesino M, Labrie F, Archer DF, Zerhouni J, Côté I, Lavoie L, Beauregard A, Martel C, Vaillancourt M, Moyneur E, Balser J. Evaluation of the acceptability of intravaginal prasterone ovule administration using an applicator. Gynecol Endocrinol. 2016;32(3):240-5. doi: 10.3109/09513590.2015.1110140. Epub 2016 Jan 6. PubMed PMID: 26634942. 12: Sánchez-Guerrero J, Fragoso-Loyo HE, Neuwelt CM, Wallace DJ, Ginzler EM, Sherrer YR, McIlwain HH, Freeman PG, Aranow C, Petri MA, Deodhar AA, Blanton E, Manzi S, Kavanaugh A, Lisse JR, Ramsey-Goldman R, McKay JD, Kivitz AJ, Mease PJ, Winkler AE, Kahl LE, Lee AH, Furie RA, Strand CV, Lou L, Ahmed M, Quarles B, Schwartz KE. Effects of prasterone on bone mineral density in women with active systemic lupus erythematosus receiving chronic glucocorticoid therapy. J Rheumatol. 2008 Aug;35(8):1567-75. Epub 2008 Jul 15. PubMed PMID: 18634158. 13: Mease PJ, Ginzler EM, Gluck OS, Schiff M, Goldman A, Greenwald M, Cohen S, Egan R, Quarles BJ, Schwartz KE. Effects of prasterone on bone mineral density in women with systemic lupus erythematosus receiving chronic glucocorticoid therapy. J Rheumatol. 2005 Apr;32(4):616-21. PubMed PMID: 15801015. 14: Bouchard C, Labrie F, Archer DF, Portman DJ, Koltun W, Elfassi É, Grainger DA, Ayotte N, Cooper TA, Martens M, Waldbaum AS, Labrie C, Côté I, Lavoie L, Martel C, Balser J; VVA Prasterone Group. Decreased efficacy of twice-weekly intravaginal dehydroepiandrosterone on vulvovaginal atrophy. Climacteric. 2015;18(4):590-607. doi: 10.3109/13697137.2014.992012. Epub 2015 Mar 3. PubMed PMID: 25511551. 15: Meno-Tetang GM, Blum RA, Schwartz KE, Jusko WJ. Effects of oral prasterone (dehydroepiandrosterone) on single-dose pharmacokinetics of oral prednisone and cortisol suppression in normal women. J Clin Pharmacol. 2001 Nov;41(11):1195-205. PubMed PMID: 11697752. 16: Martel C, Labrie F, Archer DF, Ke Y, Gonthier R, Simard JN, Lavoie L, Vaillancourt M, Montesino M, Balser J, Moyneur É; other participating members of the Prasterone Clinical Research Group. Serum steroid concentrations remain within normal postmenopausal values in women receiving daily 6.5mg intravaginal prasterone for 12 weeks. J Steroid Biochem Mol Biol. 2016 May;159:142-53. doi: 10.1016/j.jsbmb.2016.03.016. Epub 2016 Mar 10. PubMed PMID: 26972555. 17: Petri MA, Lahita RG, Van Vollenhoven RF, Merrill JT, Schiff M, Ginzler EM, Strand V, Kunz A, Gorelick KJ, Schwartz KE; GL601 Study Group. Effects of prasterone on corticosteroid requirements of women with systemic lupus erythematosus: a double-blind, randomized, placebo-controlled trial. Arthritis Rheum. 2002 Jul;46(7):1820-9. PubMed PMID: 12124866. 18: Petri MA, Mease PJ, Merrill JT, Lahita RG, Iannini MJ, Yocum DE, Ginzler EM, Katz RS, Gluck OS, Genovese MC, Van Vollenhoven R, Kalunian KC, Manzi S, Greenwald MW, Buyon JP, Olsen NJ, Schiff MH, Kavanaugh AF, Caldwell JR, Ramsey-Goldman R, St Clair EW, Goldman AL, Egan RM, Polisson RP, Moder KG, Rothfield NF, Spencer RT, Hobbs K, Fessler BJ, Calabrese LH, Moreland LW, Cohen SB, Quarles BJ, Strand V, Gurwith M, Schwartz KE. Effects of prasterone on disease activity and symptoms in women with active systemic lupus erythematosus. Arthritis Rheum. 2004 Sep;50(9):2858-68. PubMed PMID: 15452837. 19: McNamara KM, Sasano H. The intracrinology of breast cancer. J Steroid Biochem Mol Biol. 2015 Jan;145:172-8. doi: 10.1016/j.jsbmb.2014.04.004. Epub 2014 Apr 19. Review. PubMed PMID: 24751707. 20: Ke Y, Labrie F, Gonthier R, Simard JN, Bergeron D, Martel C, Vaillancourt M, Montesino M, Lavoie L, Archer DF, Balser J, Moyneur E; other participating Members of the Prasterone Clinical Research Group. Serum levels of sex steroids and metabolites following 12 weeks of intravaginal 0.50% DHEA administration. J Steroid Biochem Mol Biol. 2015 Nov;154:186-96. doi: 10.1016/j.jsbmb.2015.08.016. Epub 2015 Aug 17. PubMed PMID: 26291918.