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| Targets |
5alpha-Pregnane-3beta,6alpha-diol-20-one is a progesterone metabolite that functions as a mitogenic factor in certain cell types. It can be produced in starved androgen-responsive prostate cancer cells. The compound's mitogenic activity suggests it may stimulate cell proliferation through interaction with steroid hormone receptors or other signaling pathways. Human fibroblasts convert progesterone into this metabolite, indicating its role in progesterone metabolism. The compound is a valuable tool for studying steroid metabolism and hormone signaling.
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| ln Vitro |
Human fibroblasts convert progesterone into 5α-pregnane-3β, 6α-diol-20-one[1]. In the C4.2 cell line, progesterone and pregnenolone underwent substantial metabolism to produce 5α-pregnan-3β and 6α-diol-20-one, respectively, with nearly full conversion occurring after 24 and 18 hours. Pregnan-3β and 6α-diol-20-one, which are dependent on 3β-HSD activity but independent of CYP17A1, are preferentially formed by early steroid precursors [2].
In vitro, 5alpha-Pregnane-3beta,6alpha-diol-20-one is a mitogenic metabolite of progesterone. It is produced in starved androgen-responsive prostate cancer cells. Progesterone is converted to 5alpha-pregnane-3beta,6alpha-diol-20-one in human fibroblasts. In the C4.2 cell line, progesterone and pregnenolone undergo extensive metabolism to produce 5alpha-pregnan-3beta,6alpha-diol-20-one, with nearly complete conversion after 18-24 hours. These properties make it a valuable tool for studying steroid metabolism. |
| ln Vivo |
In vivo, 5alpha-Pregnane-3beta,6alpha-diol-20-one is a naturally occurring progesterone metabolite. It can be produced in starved androgen-responsive prostate cancer cells. The compound's role as a mitogenic metabolite suggests it may have biological activity in vivo, potentially influencing cell proliferation in certain tissues. Its presence as a progesterone metabolite indicates it is part of normal steroid metabolism. Further in vivo studies are needed to fully characterize its physiological and pathological roles.
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| Enzyme Assay |
For in vitro biochemical assays, 5alpha-Pregnane-3beta,6alpha-diol-20-one can be analyzed using chromatographic methods such as HPLC or GC-MS to study steroid metabolism. The compound can be used as a standard for identifying and quantifying progesterone metabolites in biological samples. Its conversion from progesterone can be studied in cell culture systems using radiolabeled or stable isotope-labeled precursors. Standard assay conditions include appropriate cell culture media and incubation times for metabolite production.
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| Cell Assay |
For in vitro cellular experiments, 5alpha-Pregnane-3beta,6alpha-diol-20-one is tested in cell lines to evaluate its mitogenic activity and effects on cell proliferation. Cells such as prostate cancer cells or fibroblasts are cultured in appropriate media and treated with various concentrations of the compound. Cell proliferation is assessed using standard assays such as MTT, BrdU incorporation, or cell counting. The compound's effects on cell cycle progression and signaling pathways are investigated. Its metabolism from progesterone can also be studied in these systems.
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| Animal Protocol |
For in vivo animal experiments, 5alpha-Pregnane-3beta,6alpha-diol-20-one can be administered to rodents via various routes including oral gavage, intravenous injection, or intraperitoneal injection. The compound's effects on prostate cancer growth, steroid metabolism, or other physiological processes can be evaluated in appropriate animal models. Typical doses may range from 1 to 50 mg/kg. Tissue samples are collected for analysis of steroid metabolites and markers of cell proliferation. Animal studies should follow appropriate ethical guidelines.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 5alpha-Pregnane-3beta,6alpha-diol-20-one are not extensively characterized in the literature. As a steroid metabolite with a molecular weight of 334.49, it is expected to have moderate lipophilicity and tissue distribution. When administered systemically, the compound would likely be metabolized by steroid-metabolizing enzymes in the liver and other tissues. Its half-life in circulation would depend on its stability and clearance mechanisms. Further pharmacokinetic studies would be needed to fully characterize its profile.
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| Toxicity/Toxicokinetics |
Toxicological data for 5alpha-Pregnane-3beta,6alpha-diol-20-one are limited, as it is a naturally occurring steroid metabolite. As a mitogenic metabolite, it could potentially stimulate cell proliferation, which may have implications for cancer research. Standard toxicological assessments would include cytotoxicity screening in relevant cell lines and evaluation of its effects on cell proliferation. As with all research chemicals, appropriate safety precautions should be taken when handling this compound.
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| References |
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| Additional Infomation |
5alpha-Pregnane-3beta,6alpha-diol-20-one is a research compound used to study steroid metabolism and hormone signaling. No clinical trials or regulatory approvals have been reported for this compound as a therapeutic agent. It is available from various chemical suppliers for research purposes only. The compound is a mitogenic metabolite of progesterone produced in starved androgen-responsive prostate cancer cells and is converted from progesterone in human fibroblasts.
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| Molecular Formula |
C21H34O3
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|---|---|
| Molecular Weight |
334.49286
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| Exact Mass |
334.25
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| CAS # |
21853-11-2
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| PubChem CID |
11035016
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| Appearance |
White to off-white solid powder
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| LogP |
3.5
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
24
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| Complexity |
531
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| Defined Atom Stereocenter Count |
9
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| SMILES |
C[C@@]12[C@]3([H])[C@](C[C@H](O)[C@@]1([H])C[C@@H](O)CC2)([H])[C@@]4([H])[C@@](C)([C@@H](C(C)=O)CC4)CC3
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| InChi Key |
HHUZGDMRRLQZIQ-WAXVQEINSA-N
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| InChi Code |
InChI=1S/C21H34O3/c1-12(22)15-4-5-16-14-11-19(24)18-10-13(23)6-8-21(18,3)17(14)7-9-20(15,16)2/h13-19,23-24H,4-11H2,1-3H3/t13-,14-,15+,16-,17-,18+,19-,20+,21+/m0/s1
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| Chemical Name |
1-[(3S,5S,6S,8R,9S,10R,13S,14S,17S)-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
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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 : ~100 mg/mL (~298.96 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.47 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 (7.47 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 (7.47 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 | 2.9896 mL | 14.9481 mL | 29.8963 mL | |
| 5 mM | 0.5979 mL | 2.9896 mL | 5.9793 mL | |
| 10 mM | 0.2990 mL | 1.4948 mL | 2.9896 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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