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Etiocholanolone (5β-Androsterone)

Cat No.:V51181 Purity: ≥98%
Etiocholanolone (5β-Androsterone) is a testosterone excretion aid with anticonvulsant (antiepileptic/antiseizure) activity.
Etiocholanolone (5β-Androsterone)
Etiocholanolone (5β-Androsterone) Chemical Structure CAS No.: 53-42-9
Product category: GABA Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price
100mg
500mg

Other Forms of Etiocholanolone (5β-Androsterone):

  • Etiocholanolone-d5
  • Etiocholanolone-d2
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Etiocholanolone (5β-Androsterone) is a testosterone excretion aid with anticonvulsant (antiepileptic/antiseizure) activity. Relative to its enantiomeric form, etiocholanolone is a weaker PAM (positive allosteric modulator) of the neurosterol-like GABAA receptor.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
When ethiocholesterone (10 μM) is administered in conjunction with GABA, the relative frequency of long openings increases (OT3 percent, site A2 effect). However, it has no effect on the duration of long openings (site B effect) or the relative frequency invalid. The closure time component's frequency linked to activation (the site A1 effect) [2].
ln Vivo
Etiocholanolone (ip; 0-109.1 mg/kg; single dosage) had ED50 values of 57.6 and 109.1 mg/kg in the 6-Hz and PTZ tests, respectively. The protective activity in the 5β,3α-A 6-Hz test lasted 2 hours, which was shorter than ent-5β,3α-A therapy (3 hours) in mice [1].
ADME/Pharmacokinetics
Metabolism / Metabolites
Etiocholanolone has known human metabolites that include Etiocholanolone glucuronide.
References

[1]. Natural and Enantiomeric Etiocholanolone Interact With Distinct Sites on the Rat alpha1beta2gamma2L GABAA Receptor. Mol Pharmacol. 2007 Jun;71(6):1582-90.

[2]. Anticonvulsant Potencies of the Enantiomers of the Neurosteroids Androsterone and Etiocholanolone Exceed Those of the Natural Forms. Psychopharmacology (Berl). 2014 Sep;231(17):3325-32.

Additional Infomation
3alpha-hydroxy-5beta-androstan-17-one is an androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals. It has a role as a human metabolite and a mouse metabolite. It is a 3alpha-hydroxy steroid, a 17-oxo steroid and an androstanoid. It derives from a hydride of a 5beta-androstane.
Etiocholanolone has been reported in Homo sapiens with data available.
Etiocholanolone is a 17-ketosteroid which excreted in the urine as a metabolite of steroid hormones. The most common form of etiocholanolone present in the urine is the sulfate salt. This agent, also known as 5-isoandrosterone, may be used to evaluate adrenal cortex function, bone marrow performance and, in neoplastic disease, for immunostimulation. (NCI04)
The 5-beta-reduced isomer of ANDROSTERONE. Etiocholanolone is a major metabolite of TESTOSTERONE and ANDROSTENEDIONE in many mammalian species including humans. It is excreted in the URINE.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H30O2
Molecular Weight
290.44
Exact Mass
290.224
CAS #
53-42-9
Related CAS #
Etiocholanolone-d5;1620102-33-1;Etiocholanolone-d2;2687960-82-1
PubChem CID
5880
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
413.1±45.0 °C at 760 mmHg
Melting Point
148~150°C (lit.)
Flash Point
176.4±21.3 °C
Vapour Pressure
0.0±2.2 mmHg at 25°C
Index of Refraction
1.536
LogP
3.75
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Heavy Atom Count
21
Complexity
459
Defined Atom Stereocenter Count
7
SMILES
C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
InChi Key
QGXBDMJGAMFCBF-BNSUEQOYSA-N
InChi Code
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
Chemical Name
(3R,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
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~172.15 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.4431 mL 17.2153 mL 34.4305 mL
5 mM 0.6886 mL 3.4431 mL 6.8861 mL
10 mM 0.3443 mL 1.7215 mL 3.4431 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.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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