| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| 500mg |
| Targets |
Etiocholanolone targets the GABAA receptor as a less potent neurosteroid positive allosteric modulator (PAM) compared to its enantiomer. It has anticonvulsant activity in animal models. As a metabolite, it also interacts with androgen receptors but with significantly lower affinity compared to testosterone.
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| 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].
In vitro, Etiocholanolone (0.1-100 uM) enhances GABAA receptor-mediated chloride currents in patch-clamp recordings of recombinant GABAA receptors expressed in HEK-293 cells. It acts as a positive allosteric modulator, increasing the frequency and duration of channel opening. The EC50 for GABAA receptor modulation is in the low micromolar range. |
| 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].
In vivo, Etiocholanolone (10-100 mg/kg, intraperitoneal) demonstrates anticonvulsant activity in rodent models of seizures, including pentylenetetrazole (PTZ)-induced seizures and maximal electroshock (MES) tests. It prolongs the latency to seizure onset and reduces seizure severity. The compound also has weak androgenic activity in castrated male rat models. |
| Enzyme Assay |
For non-cellular binding, purified GABAA receptor-enriched membrane fractions are prepared from rat brains. Radioligand binding assays are performed using [3H]muscimol or [35S]TBPS (tert-butylbicyclophosphorothionate) in the presence of varying concentrations of Etiocholanolone (1 nM-100 uM). Non-specific binding is determined using GABA or picrotoxin.
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| Cell Assay |
For cell-based GABAA receptor functional assays, HEK-293 cells stably expressing recombinant GABAA receptor subunits (alpha1beta2gamma2) are loaded with a fluorescent membrane potential dye (e.g., FLIPR Membrane Potential Dye). Cells are pre-incubated with Etiocholanolone (0.1-100 uM) for 5 minutes, and fluorescence changes are measured upon GABA (EC20) stimulation.
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| Animal Protocol |
For in vivo anticonvulsant evaluation, male Swiss-Webster mice or Sprague-Dawley rats are injected intraperitoneally with Etiocholanolone (10-100 mg/kg) in a vehicle (e.g., 5% DMSO, 10% Tween-80 in saline). After 30-60 minutes, seizures are induced by pentylenetetrazole (40-50 mg/kg, i.p.) or by maximal electroshock (50 mA, 0.2 sec). Latency to clonic seizures, duration of seizures, and mortality are recorded.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
It is known that human metabolites of acetylcholine include acetylcholine glucuronide. Etiocholanolone is an endogenous metabolite with a half-life in humans of approximately 2-4 hours after parenteral administration. It is metabolized primarily by hepatic conjugation (glucuronidation) and excreted in urine. Oral bioavailability is low due to extensive first-pass metabolism. |
| Toxicity/Toxicokinetics |
Etiocholanolone is generally well tolerated at moderate doses. Acute toxicity studies report LD50 values of approximately 1000 mg/kg in rodents after intraperitoneal administration. High doses may cause sedation, ataxia, and hepatotoxicity. As a neurosteroid, it may cause dizziness, drowsiness, and hormonal effects with prolonged use.
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| References |
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| Additional Infomation |
3α-Hydroxy-5β-androstan-17-one is an androsteroid compound formed by replacing 5β-androstanane with an α-hydroxyl group at the 3-position and a carbonyl group at the 17-position. It is a metabolite of testosterone in mammals and has been found in both humans and mice. It is a 3α-hydroxy steroid, a 17-carbonyl steroid, and an androsteroid compound derived from the hydrogenation of 5β-androstanane. There are reports and data regarding the presence of androstanone in humans. Androstanone is a 17-keto steroid that is excreted in urine as a metabolite of steroid hormones. The most common form of androstanone in urine is sulfate. This reagent, also known as 5-isoandrosone, can be used to assess adrenal cortex function, bone marrow function, and for immunostimulation in neoplastic diseases. (NCI04) Androstanone is the 5β-reduced isomer of androstenedione. In many mammals, including humans, androstanone is a major metabolite of testosterone and androstenedione. It is excreted in urine.
Etiocholanolone is a naturally occurring steroid metabolite and has been used in clinical diagnostic tests for adrenal and gonadal function. It is not an approved drug but serves as a research tool for studying steroid metabolism and GABAA receptor modulation. The compound has been investigated for immune stimulation in neoplastic diseases but is not in clinical use. |
| Molecular Formula |
C19H30O2
|
|---|---|
| Molecular Weight |
290.44
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| Exact Mass |
290.224
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| CAS # |
53-42-9
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| Related CAS # |
Etiocholanolone-d5;1620102-33-1;Etiocholanolone-d2;2687960-82-1
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| PubChem CID |
5880
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
413.1±45.0 °C at 760 mmHg
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| Melting Point |
148～150°C (lit.)
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| Flash Point |
176.4±21.3 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.536
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| LogP |
3.75
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
21
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| Complexity |
459
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| 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
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| 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
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| 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
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~172.15 mM)
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|---|---|
| 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. View More
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. |
| 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.
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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