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7β-Hydroxy-epi-androsterone (7β-Hydroxy-EpiA) 25848-69-5

7β-Hydroxy-epi-androsterone (7β-Hydroxy-EpiA) 25848-69-5

CAS No.: 25848-69-5

7β-Hydroxy-epi-androsterone (7β-Hydroxy-EpiA) binds to ERβ and has anti~inflammatory and neuro-protective (neuro-prot
Data collection:peptidedb@qq.com

This product is for research use only, not for human use. We do not sell to patients.

7β-Hydroxy-epi-androsterone (7β-Hydroxy-EpiA) binds to ERβ and has anti~inflammatory and neuro-protective (neuro-protection) properties. 7β-Hydroxy-epi-androsterone is the endogenous androgen analogue of dehydroepiandrosterone.

Physicochemical Properties


Molecular Formula C19H30O3
Molecular Weight 306.44
Exact Mass 306.219
CAS # 25848-69-5
PubChem CID 9836181
Appearance Typically exists as solid at room temperature
LogP 2.3
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 3
Rotatable Bond Count 0
Heavy Atom Count 22
Complexity 489
Defined Atom Stereocenter Count 8
SMILES

C[C@]12CC[C@@H](C[C@@H]1C[C@@H]([C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O)O

InChi Key VFPMCLQMAUVEHD-UCPSWNCLSA-N
InChi Code

InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h11-15,17,20-21H,3-10H2,1-2H3/t11-,12+,13+,14+,15+,17+,18+,19+/m1/s1
Chemical Name

(3S,5R,7S,8R,9S,10S,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets ERβ
ln Vitro 7β-Hydroxy-epi-androsterone (1, 10 and 100 nM, 72 hours) suppresses MCF-7 and MDA-MB-231 cell proliferation in the presence of E2 (10 nM) [2]. 7β-Hydroxy-epi-androsterone (1, 10 and 100 nM, 48 hours) causes G0/G1 cell cycle arrest in MCF-7 and MDA-MB-231 cells [2]. 7β-Hydroxy-epi-androsterone (1, 10 and 100 nM, 48 hours) promotes apoptosis in MCF-7 cells in the presence of E2 (10 nM) [2]. 7β-Hydroxy-epi-androsterone (1, 10 and 100 nM, 24 hours) binds to ERβ and inhibits transactivation in MDA-MB-231 cells [2].
ln Vivo In rats with DSS-induced colitis, 7β-Hydroxy-epi-androsterone (ip; once daily for seven days) demonstrated anti-inflammatory benefits[3]. In rats with Alzheimer's disease, 7β-Hydroxyepi-androsterone (0.1 mg/kg subcutaneously twice daily for 10 days) shows protective benefits against glial cell death and inflammatory neurodegeneration[4].
Cell Assay Apoptosis Analysis[2]
Cell Types: MCF-7 cells
Tested Concentrations: 1, 10 and 100 nM (in presence of 10 nM E2)
Incubation Duration: 48 h
Experimental Results: Increased cell apoptosis in presence of E2.
Animal Protocol Animal/Disease Models: Rat with DSS-induced colitis[3]
Doses: 0.01, 0.1 and 1 mg/kg
Route of Administration: intraperitoneal (ip) injection (ip), one time/day for 7 days.
Experimental Results: Increased in COX-2 and PGE synthase expression. Increased colonic tissue levels of 15d-PGJ2 levels.
References [1]. Christophe Ricco, et al. Synthesis of 7β-hydroxy-epiandrosterone. Steroids. Volume 76, Issues 1-2, January 2011, Pages 28-30.
[2]. Sandra N, et al. The DHEA metabolite 7β-hydroxy-epiandrosterone exerts anti-estrogenic effects on breast cancer cell lines. Steroids. 2012 Apr;77(5):542-51.
[3]. Hennebert O, et al. Anti-inflammatory effects and changes in prostaglandin patterns induced by 7beta-hydroxy-epiandrosterone in rats with colitis. J Steroid Biochem Mol Biol. 2008 Jun;110(3-5):255-62.
[4]. Dudas B, et al. Protection against inflammatory neurodegeneration and glial cell death by 7beta-hydroxy epiandrosterone, a novel neurosteroid. Neurobiol Dis. 2004 Mar;15(2):262-8.
Additional Infomation 7beta-hydroxyepiandrosterone is a 3beta-hydroxy steroid that is epiandrosterone carrying a hydroxy group at the 7beta position. It is an endogenous androgen metabolite that has been shown to exert neuroprotective effects. It has a role as a human metabolite, a neuroprotective agent, an estrogen receptor antagonist and an androgen. It is a 17-oxo steroid, a 7beta-hydroxy steroid, a 3beta-hydroxy steroid and an androstanoid. It is functionally related to an epiandrosterone.
Drug Indication
Investigated for use/treatment in alzheimer's disease.

Solubility Data


Solubility (In Vitro) May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2633 mL 16.3164 mL 32.6328 mL
5 mM 0.6527 mL 3.2633 mL 6.5266 mL
10 mM 0.3263 mL 1.6316 mL 3.2633 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.