Dehydroepiandrosterone | DHEA | CAS#53-43-0

MedKoo Cat#: 326944 | Name: Dehydroepiandrosterone

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Description:

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

Dehydroepiandrosterone, also known as trans-Dehydroandrosterone, DHEA, more correctly didehydroepiandrosterone; androstenolone and 3β-hydroxyandrost-5-en-17-one or 5-androsten-3β-ol-17-one, is an endogenous steroid hormone. It is the most abundant circulating steroid hormone in humans, in whom it is produced in the adrenal glands, the gonads, and the brain, where it functions predominantly as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid.

Chemical Structure

Dehydroepiandrosterone

CAS#53-43-0

Theoretical Analysis

MedKoo Cat#: 326944

Name: Dehydroepiandrosterone

CAS#: 53-43-0

Chemical Formula: C19H28O2

Exact Mass: 288.2089

Molecular Weight: 288.43

Elemental Analysis: C, 79.12; H, 9.79; O, 11.09

Price and Availability

Size	Price	Availability
1g	USD 90.00	Ready to Ship
2g	USD 150.00	Ready to ship
5g	USD 300.00	Ready to Ship

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Related CAS #

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Synonym

Androstenolone; trans-Dehydroandrosterone; DHEA; Diandrone; NSC 9896; Prasterone; Psicosterone; DHEA; EL-10; GL-701; IP-1001; IPL-1001; PB-007; SH-K-04828;

IUPAC/Chemical Name

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

InChi Key

FMGSKLZLMKYGDP-USOAJAOKSA-N

InChi Code

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

SMILES Code

C[C@]1([C@](CC2)([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC1)C2=O

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

Certificate of Analysis

View CoA: current batch, Lot#S8G10M12

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

DHEA (Prasterone) mediates its action via multiple signaling pathways involving specific membrane receptors and via transformation into androgen and estrogen derivatives acting through their specific receptors.

In vitro activity:

ROS, ·OH and MDA contents were significantly increased in H2O2-treated group when compared to control group (P < 0.05) (Figure 2). Pre-treatment with 10μM DHEA reduced intracellular ROS levels relative to that in H2O2-treated group (P < 0.05) (Figure 2A). Pre-treatment with 1-100μM DHEA significantly decreased ·OH content (P < 0.01) (Figure 2B), while no significant differences were observed on the O2- content (Figure 2C). Compared to H2O2-treated group, MAD contents were decreased in the cells pre-treated with 10 and100μM DHEA (P < 0.05) (Figure 2D). Reference: Oncotarget. 2017 Mar 7; 8(10): 16158–16169. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369954/

In vivo activity:

Significantly fewer CD86+/Iba-1+ microglia were accumulated in the affected area in the SAH + DHEA group than in the SAH group, although the proportions were not significantly different (Fig. (Fig.3a,3a, d, n = 6 fields from 3 independent experiments). Moreover, a significantly higher number and percentage of CD206+/Iba-1+ microglia were detected in the SAH + DHEA group than in the SAH group (Fig. (Fig.3a,3a, d). In addition, the microglia exhibited an intermediate morphology between rest and activation in the presence of DHEA (Fig. (Fig.3a).3a). Together, the IF images and qPCR results indicated that DHEA may inhibit SAH-induced proinflammatory microglial activation in vivo. Reference: J Neuroinflammation. 2019; 16: 243. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6883548/

	Solvent	mg/mL	mM
Solubility
	DMSO	53.5	185.49
	DMF	25.0	86.68
	Ethanol	53.5	185.49
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.73

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 288.43 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

Formulation protocol:

1. Joshi K, Hassan SS, Ramaraj P. Differential biological effects of dehydroepiandrosterone (DHEA) between mouse (B16F10) and human melanoma (BLM) cell lines. Dermatoendocrinol. 2017 Nov 20;9(1):e1389360. doi: 10.1080/19381980.2017.1389360. PMID: 29484102; PMCID: PMC5821161. 2. Ding X, Yu L, Ge C, Ma H. Protective effect of DHEA on hydrogen peroxide-induced oxidative damage and apoptosis in primary rat Leydig cells. Oncotarget. 2017 Mar 7;8(10):16158-16169. doi: 10.18632/oncotarget.15300. PMID: 28212544; PMCID: PMC5369954. 3. Tao T, Liu GJ, Shi X, Zhou Y, Lu Y, Gao YY, Zhang XS, Wang H, Wu LY, Chen CL, Zhuang Z, Li W, Hang CH. DHEA Attenuates Microglial Activation via Induction of JMJD3 in Experimental Subarachnoid Haemorrhage. J Neuroinflammation. 2019 Nov 28;16(1):243. doi: 10.1186/s12974-019-1641-y. PMID: 31779639; PMCID: PMC6883548. 4. Qiu X, Gui Y, Xu Y, Li D, Wang L. DHEA promotes osteoblast differentiation by regulating the expression of osteoblast-related genes and Foxp3(+) regulatory T cells. Biosci Trends. 2015 Oct;9(5):307-14. doi: 10.5582/bst.2015.01073. PMID: 26559023.

In vitro protocol:

In vivo protocol:

1. Tao T, Liu GJ, Shi X, Zhou Y, Lu Y, Gao YY, Zhang XS, Wang H, Wu LY, Chen CL, Zhuang Z, Li W, Hang CH. DHEA Attenuates Microglial Activation via Induction of JMJD3 in Experimental Subarachnoid Haemorrhage. J Neuroinflammation. 2019 Nov 28;16(1):243. doi: 10.1186/s12974-019-1641-y. PMID: 31779639; PMCID: PMC6883548. 2. Qiu X, Gui Y, Xu Y, Li D, Wang L. DHEA promotes osteoblast differentiation by regulating the expression of osteoblast-related genes and Foxp3(+) regulatory T cells. Biosci Trends. 2015 Oct;9(5):307-14. doi: 10.5582/bst.2015.01073. PMID: 26559023.

1: 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. 2: 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. 3: Labrie F, Derogatis L, 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; Members of the VVA Prasterone Research Group. Effect of Intravaginal Prasterone on Sexual Dysfunction in Postmenopausal Women with Vulvovaginal Atrophy. J Sex Med. 2015 Dec;12(12):2401-12. doi: 10.1111/jsm.13045. Epub 2015 Nov 23. PubMed PMID: 26597311. 4: 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. 5: 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. 6: 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. 7: 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. 8: 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. 9: 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. 10: Labrie F, Archer DF, Bouchard C, Fortier M, Cusan L, Gomez JL, Girard G, Baron M, Ayotte N, Moreau M, Dubé R, Côté I, Labrie C, Lavoie L, Berger L, Gilbert L, Martel C, Balser J. Intravaginal dehydroepiandrosterone (prasterone), a highly efficient treatment of dyspareunia. Climacteric. 2011 Apr;14(2):282-8. doi: 10.3109/13697137.2010.535226. Epub 2011 Jan 18. PubMed PMID: 21244215. 11: 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. 12: 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, Berger L, Gilbert L, Martel C, Balser J. Intravaginal dehydroepiandrosterone (Prasterone), a physiological and highly efficient treatment of vaginal atrophy. Menopause. 2009 Sep-Oct;16(5):907-22. doi: 10.1097/gme.0b013e31819e8e2d. PubMed PMID: 19436225. 13: 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, Berger L, Gilbert L, Martel C, Balser J. Effect of intravaginal dehydroepiandrosterone (Prasterone) on libido and sexual dysfunction in postmenopausal women. Menopause. 2009 Sep-Oct;16(5):923-31. doi: 10.1097/gme.0b013e31819e85c6. PubMed PMID: 19424093. 14: Shervington LA, Smith N, Norman E, Ward T, Phillips R, Shervington A. To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines. Eur J Med Chem. 2009 Jul;44(7):2944-51. doi: 10.1016/j.ejmech.2008.11.014. Epub 2008 Dec 9. PubMed PMID: 19121874. 15: 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. 16: Kocis P. Prasterone. Am J Health Syst Pharm. 2006 Nov 15;63(22):2201-10. Review. PubMed PMID: 17090740. 17: Alexander T, Friel PN, Wright JV. Prasterone and bone mineral density in women with systemic lupus erythematosus. J Rheumatol. 2005 Dec;32(12):2497; author reply 2497-8. PubMed PMID: 16331796. 18: 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. 19: 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. 20: Ramsey-Goldman R. Prasterone treatment in systemic lupus erythematosus. Curr Rheumatol Rep. 2003 Oct;5(5):348. PubMed PMID: 14570076.