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 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.

---

Dehydroepiandrosterone (DHEA) fed at 0.4% in the diet is known to exert strong antihyperglycemic effects in C57BL/KsJ genetically diabetic (db/db) mice. Three of the major metabolic products of DHEA; DHEA sulfate, alpha-hydroxyetiocholanolone (alpha-ET), and beta-hydroxyetiocholanolone (beta-ET) when fed at 0.1% in the diet, and one putative product, 17 beta-estradiol, when fed at 0.005% also prevented the development of severe diabetes while having little effect on the amount of food eaten or the rate of weight gain. When suboptimal doses (5-20 micrograms/week) of estradiol were injected in combination with diets containing either alpha-ET or beta-ET, marked potentiating effect was noted, normalization of the hyperglycemia being produced with as little as 0.025% of beta-ET and 0.05% of alpha-ET. The ability of the etiocholanolones to maintain islet integrity and prevent the development of most diabetes symptoms suggests that these metabolites are not merely inactive end products of steroid metabolism, but are physiological effectors in their own right.[1]

---

Electroencephalographic synchronization and a fall in the multiunit activity was observed in the mesencephalic reticular formation, ventromedial hypothalamus and dorsal hippocampus following intravenous administration of some 5 alpha and 5 beta-reduced testosterone derivatives. The most potent compounds were androsterone and androstanediol which have the 3 alpha-hydroxy-5 alpha ring A configuration. Steroids with 5 beta reduction, i.e. 5 beta-dihydrotestosterone, etiocholanolone and epi-etiocholanolone, at high doses produced the inhibitory effect. Testosterone and its closer 5 alpha metabolites (5 alpha-dihydrotestosterone and 5 alpha-androstanedione) were ineffective. The depressive effect of androsterone on neurones was antagonized by the intraventricular injection of ruthenium red. On the other hand, the convulsant effect of ruthenium red was prevented or diminished by the action of androsterone. These findings support the hypothesis that testosterone metabolites reduced either at 5 alpha or 5 beta position can act in the brain at a membrane level and raise the possibility that testosterone may be a prehormone in the regulation of excitability in some 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

154-156ºC

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.

---

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).

View More

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 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).

View More

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.)