Endogenous metabolite

Epietiocholanolone is a 3beta-hydroxy steroid that is 5beta-androstane substituted by a hydroxy group at position 3beta and an oxo group at position 17. It is a metabolite of testosterone. It has a role as an androgen, a human blood serum metabolite, a mouse metabolite, a rat metabolite and an animal metabolite. It is a 3beta-hydroxy steroid, a 17-oxo steroid and an androstanoid. It derives from a hydride of a 5beta-androstane.

The ineffectiveness of 5β-Androstan-3β-ol-17-one (2 mg/mouse; subcutaneous injection; once daily for 4 weeks) implies that some biotransformation is necessary for these metabolites to function properly[1]. Added to food, 5β-Androstan-3β-ol-17-one (oral treatment; 18 weeks total; mass ratios of 0.025%, 0.05%, and 0.1%, respectively) protects against severe diabetes in mice and controls hyperglycemia. normalization without influencing food consumption or rates of weight gain[1]. When administered intravenously in a single dose, 5β-Androstan-3β-ol-17-one (1 mg/kg–20 mg/kg) exhibits a potent inhibitory action on adult male cat neurons[2].

Animal/Disease Models: C57BL/KsJ genetically diabetic (db/db) mice model[1]
Doses: 0.025%, 0.05%, 0.1% in diet
Route of Administration: Oral gavage; filled the diet every second day; for 18 weeks
Experimental Results: Exerted strong antihyperglycemic effects.

[1]. Coleman DL, et al. Therapeutic effects of dehydroepiandrosterone metabolites in diabetes mutant mice (C57BL/KsJ-db/db). Endocrinology. 1984 Jul;115(1):239-43.
[2]. Kubli-Garfias C, et al. Depressant effect of androgens on the cat brain electrical activity and its antagonism by ruthenium red. Neuroscience. 1982;7(11):2777-82.

Epietiocholanolone (DHEA) is a 3β-hydroxy steroid, formed by replacing the 3β-hydroxy group with a hydroxyl group at the 3β-position and the 17-position with a carbonyl group on 5β-androstane. It is a metabolite of testosterone. It is an androgen and a metabolite found in human serum, mice, rats, and other animals. It is a 3β-hydroxy steroid, a 17-carbonyl steroid, and an androstane compound. It is derived from the hydrogenation of 5β-androstane.

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Adding 0.4% dehydroepiandrosterone (DHEA) to the diet of C57BL/KsJ hereditary diabetic (db/db) mice is known to produce a significant hypoglycemic effect. The three main metabolites of DHEA are: dietary addition of 0.1% dehydroepiandrosterone sulfate (DHEA-S), α-hydroxyestradiol (α-ET), and β-hydroxyestradiol (β-ET), and the addition of 0.005% 17β-estradiol (a speculative product). All of these prevent the development of severe diabetes with minimal effect on food intake or weight gain. A significant enhancement was observed when suboptimal doses (5-20 μg/week) of estradiol were simultaneously injected into a diet containing α-ET or β-ET; only 0.025% β-ET and 0.05% α-ET were needed to normalize hyperglycemia. The ability of isothermal compounds to maintain pancreatic islet integrity and prevent most symptoms of diabetes suggests that these metabolites are not merely inactive end products of steroid metabolism, but rather possess physiological effects themselves. [1]

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Intravenous injection of certain 5α and 5β-reduced testosterone derivatives resulted in EEG synchronization and decreased multi-unit activity in the midbrain reticular formation, ventromedial hypothalamus, and dorsal hippocampus. The most potent compounds were androstenedione and androstenedione, which have a 3α-hydroxy-5α ring A configuration. High doses of 5β-reduced steroids, such as 5β-dihydrotestosterone, isandrostenedione, and epiandrostenedione, also produced inhibitory effects. Testosterone and its 5α-metabolites (5α-dihydrotestosterone and 5α-androstenedione) were ineffective. Intraventricular injection of ruthenium red antagonized the inhibitory effect of androstenedione on neurons. On the other hand, androstenedione could prevent or attenuate the convulsive effects of ruthenium red. These findings support the hypothesis that 5α- or 5β-reduced testosterone metabolites may act at the meningeal level and suggest that testosterone may act as a prohormone involved in the excitatory regulation of certain brain functions. [2]

C19H30O2

290.44

290.225

571-31-3

247732

Typically exists as solid at room temperature

1.085 g/cm3

413.1ºC at 760 mmHg

154 - 155 °C

176.4ºC

1.536

3.959

1

2

0

21

459

7

CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O

QGXBDMJGAMFCBF-XRJZGPCZSA-N

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+/m1/s1

(3S,5R,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

Epietiocholanolone; 571-31-3; 5beta-androstan-3beta-ol-17-one; 3beta-hydroxy-5beta-androstan-17-one; 5b-Epiandrosterone; beta-Etiocholanolone; 3b-hydroxy-5b-androstan-17-one; 3.beta.-Etiocholanolone;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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

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

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.

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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).

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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)

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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).

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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

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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.

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 (Please use freshly prepared in vivo formulations for optimal results.)