Epiandrosterone

steroid hormone with weak androgenic activity CAS# 481-29-8

Epiandrosterone

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Chemical structure

Epiandrosterone

3D structure

Chemical Properties of Epiandrosterone

Cas No. 481-29-8 SDF Download SDF
PubChem ID 441302 Appearance Powder
Formula C19H30O2 M.Wt 290.44
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (172.15 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
SMILES CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
Standard InChIKey QGXBDMJGAMFCBF-LUJOEAJASA-N
Standard InChI InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Epiandrosterone Dilution Calculator

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Epiandrosterone Molarity Calculator

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Preparing Stock Solutions of Epiandrosterone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4431 mL 17.2153 mL 34.4305 mL 68.861 mL 86.0763 mL
5 mM 0.6886 mL 3.4431 mL 6.8861 mL 13.7722 mL 17.2153 mL
10 mM 0.3443 mL 1.7215 mL 3.4431 mL 6.8861 mL 8.6076 mL
50 mM 0.0689 mL 0.3443 mL 0.6886 mL 1.3772 mL 1.7215 mL
100 mM 0.0344 mL 0.1722 mL 0.3443 mL 0.6886 mL 0.8608 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Epiandrosterone

IC50: Blocking L-type calcium channels of ventricular myocytes with an IC50 of 42 ± 6 M.

17-ketosteroid epiandrosterone (EPI) which formed in peripheral tissues is a metabolite of testosterone precursor dehydroepiandrosterone (DHEA). After circulation in vivo, EPI is ultimately excreted from urine. Serving as a weak androgen, EPI is proved to block the pentose phosphate pathway (PPP) and to down-regulate intracellular NADPH levels. Most importantly, EPI turns off L-type calcium channels of ventricular myocytes and restricts myocardial contractility. [1]

In vitro: It was reported that EPI, at concentrations from 10 to 100 mM, decreased left-ventricular developed pressure (LVDP) and myocardial contraction rate dose-dependently. In addition, EPI also increased CPP in isolated hearts, down-regulated levels of myocardial NADPH and nitrite, as well as relaxed rat aortic rings in the dose-dependent manner. Findings from whole cell clamp via electrophysiological analysis of single ventricular myocytes demonstrated that EPI could reversibly block L-type channel currents carried by Ba2+ in a dose-dependent manner with an IC50 of2 ± 6 M. Moreover, EPI, at a concentration of 30 mM, accelerated the decay of IBa during depolarization, which suggested this agent as a L-type Ca2+ channel antagonist with similar properties to those of 1, 4-dihydropyridine (DHP) Ca2+ channel blockers. [1]

In vivo: In vivo tests were performed using G-6-PD-low C57L/J mouse erythrocytes. Every other day, mice were orally administered with 450 or 900 mg/kg of tested agents including DHEA, EPI, pregnenolone (PREG) and androstanedione (ANDR) for seven days (four doses). Three hours after the final dose, mice were sacrificed. Findings from blood samples suggested that G-6-PD activity had no significant changes, which might be caused by the lack of receptor sites for the steroids on the erythrocyte membrane. [2]

Clinical trials: A double blind clinical trial was conducted to measure the effect of DHEA on eight psychiatric patients under conditions of constitutional inferiority, less confidence and social inadequacy. It was found that DHEA had no effect on behavior judged objectively nor did it regulated the performance in two productivity tests. [3]

References:
[1]Gupte SA, Tateyama M, Okada T, Oka M and Ochi R.  Epiandrosterone, a metabolite of testosterone precursor, blocks l-type calcium channels of ventricular myocytes and inhibits myocardial contractility. J Mol Cell Cardiol. 2002 Mar; 34: 679- 88.
[2]Calabrese EJ, Horton HM and Leonard DA.  The in vivo effects of four steroids on glucose-6-phosphate dehydrogenase activity of c57L/J mouse erythrocytes. J. Environ. Sci. Health. 1987; A22(6): 563-74.
[3]Forrest AD, Drewery J, Fotherby K and Laverty SG.  A clinical trial of dehydroepiandrosterone (diandrone). J. Neurol. Neurosurg. Psychiat. 1960; 23: 52-5.

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References on Epiandrosterone

An omics investigation into chronic widespread musculoskeletal pain reveals epiandrosterone sulfate as a potential biomarker.[Pubmed:25915148]

Pain. 2015 Oct;156(10):1845-51.

Chronic widespread musculoskeletal pain (CWP) is common, having a population prevalence of 10%. This study aimed to define the biological basis of the CWP/body mass association by using a systems biology approach. Adult female twins (n = 2444) from the TwinsUK registry who had extensive clinical, anthropometric, and "omic" data were included. Nontargeted metabolomics screening including 324 metabolites was carried out for CWP and body composition using dual-energy X-ray absorptiometry. The biological basis of these associations was explored through a genome-wide association study and replicated in an independent population sample (Cooperative Health Research in the Region of Augsburg [KORA] study, n = 2483). A causal role for the genetic variants identified was sought in CWP using a Mendelian randomisation study design. Fat mass/height2 was the body composition variable most strongly associated with CWP (TwinsUK: P = 2.4 x 10(-15) and KORA: P = 1.59 x 10(-10)). Of 324 metabolites examined, Epiandrosterone sulfate (EAS) was highly associated with both CWP (P = 1.05 x 10(-09) in TwinsUK and P = 3.70 x 10(-06) in KORA) and fat mass/height2. Genome-wide association study of EAS identified imputed single nucleotide polymorphism rs1581492 at 7q22.1 to be strikingly associated with EAS levels (P

Synthesis and antitumor evaluation of novel hybrids of phenylsulfonylfuroxan and epiandrosterone/dehydroepiandrosterone derivatives.[Pubmed:26004429]

Steroids. 2015 Sep;101:7-14.

Thirteen novel furoxan-based nitric oxide (NO) releasing hybrids (14a-e, 15a-e, 17b-d) of 16,17-pyrazo-annulated steroidal derivatives were synthesized and evaluated against the MDA-MB-231, HCC1806, SKOV-3, DU145, and HUVEC cell lines for their in vitro anti-proliferative activity. Most of the compounds displayed potent anti-proliferative effects. Among them, 17c exhibited the best activity with IC50 values of 20-1.4nM against four cell lines (MDA-MB-231, SKOV-3, DU145, and HUVEC), and 1.03muM against a tamoxifen resistant breast cancer cell line (HCC1806). Furthermore, five compounds (14a, 15a, 17b-d) were selected to screen for VEGF inhibitory activity. Compounds 15a, 17b,c showed obviously better activity than 2-Methoxyestradiol (2-ME) on reducing levels of VEGF secreted by MDA-MB-231 cell line. In a Capillary-like Tube Formation Assay, compounds 17b,c exhibited a significant suppression of the tubule formation in the concentration of 1.75nM and 58nM, respectively. The preliminary SAR showed that steroidal scaffolds with a linker in 3-position were favorable moieties to evidently increase the bioactivities of these hybrids. Overall, these results implied that 17c merited to be further investigated as a promising anti-cancer candidate.

The DHEA metabolite 7beta-hydroxy-epiandrosterone exerts anti-estrogenic effects on breast cancer cell lines.[Pubmed:22342541]

Steroids. 2012 Apr;77(5):542-51.

7beta-Hydroxy-Epiandrosterone (7beta-OH-EpiA), an endogenous androgenic derivative of dehydroEpiandrosterone, has previously been shown to exert anti-inflammatory action in vitro and in vivo via a shift from prostaglandin E2 (PGE2) to 15-deoxy-Delta(12,14)-PGJ2 production. This modulation in prostaglandin production was obtained with low concentrations of 7beta-OH-EpiA (1-100nM) and suggested that it might act through a specific receptor. Inflammation and prostaglandin synthesis is important in the development and survival of estrogen-dependent mammary cancers. Estrogen induced PGE2 production and cell proliferation via its binding to estrogen receptors (ERs) in these tumors. Our objective was to test the effects of 7beta-OH-EpiA on the proliferation (by counting with trypan blue exclusion), cell cycle and cell apoptosis (by flow cytometry) of breast cancer cell lines MCF-7 (ERalpha+, ERbeta+, G-protein coupled receptor 30: GPR30+) and MDA-MB-231 (ERalpha-, ERbeta+, GPR30+) and to identify a potential target of this steroid in these cell lineages (by transactivations) and in the nuclear ER-negative SKBr3 cells (GPR30+) (by proliferation assays). 7beta-OH-EpiA exerted anti-estrogenic effects in MCF-7 and MDA-MB-231 cells associated with cell proliferation inhibition and cell cycle arrest. Moreover, transactivation and proliferation with ER agonists assays indicated that 7beta-OH-EpiA interacted with ERbeta. Data from proliferation assays on the MCF-7, MDA-MB-231 and SKBr3 cell lines suggested that 7beta-OH-EpiA may also act through the membrane GPR30 receptor. These results support that this androgenic steroid acts as an anti-estrogenic compound. Moreover, this is the first evidence that low doses of androgenic steroid exert antiproliferative effects in these mammary cancer cells. Further investigations are needed to improve understanding of the observed actions of endogenous 7beta-OH-EpiA.

Oxidative metabolism of dehydroepiandrosterone (DHEA) and biologically active oxygenated metabolites of DHEA and epiandrosterone (EpiA)--recent reports.[Pubmed:22037250]

Steroids. 2012 Jan;77(1-2):10-26.

DehydroEpiandrosterone (DHEA) is a multifunctional steroid with a broad range of biological effects in humans and animals. DHEA can be converted to multiple oxygenated metabolites in the brain and peripheral tissues. The mechanisms by which DHEA exerts its effects are not well understood. However, evidence that the effects of DHEA are mediated by its oxygenated metabolites has accumulated. This paper will review the panel of oxygenated DHEA metabolites (7, 16 and 17-hydroxylated derivatives) including a number of 5alpha-androstane derivatives, such as Epiandrosterone (EpiA) metabolites. The most important aspects of the oxidative metabolism of DHEA in the liver, intestine and brain are described. Then, this article reviews the reported biological effects of oxygenated DHEA metabolites from recent findings with a specific focus on cancer, inflammatory and immune processes, osteoporosis, thermogenesis, adipogenesis, the cardiovascular system, the brain and the estrogen and androgen receptors.

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Epiandrosterone is a steroid hormone with weak androgenic activity.

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