5α-Pregnane-3,20-dione
Synonym(s):5α-Dihydroprogesterone;Allopregnane-3,20-dione
- CAS NO.:566-65-4
- Empirical Formula: C21H32O2
- Molecular Weight: 316.48
- MDL number: MFCD00067132
- EINECS: 209-297-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 23:02:33
What is 5α-Pregnane-3,20-dione?
The Uses of 5α-Pregnane-3,20-dione
(5α)-Pregnane-3,20-dione exerts neuroprotective effects in chronic autoimmune encephalomyelitis (EAE). The neuroactivity of the steroid acts as a therapeutic agent for multiple sclerosis.
Definition
ChEBI: 5alpha-pregnane-3,20-dione is a C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone. It has a role as a human metabolite and a progestogen. It is a 20-oxo steroid, a C21-steroid hormone and a 3-oxo-5alpha-steroid. It is functionally related to a progesterone. It derives from a hydride of a 5alpha-pregnane.
Biochem/physiol Actions
(5α)-Pregnane-3,20-dione is a high-level metabolite of progesterone in breast cancer tissue (but not normal breast tissue); promotes cell proliferation and detachment. Receptors appear only on the cell surface of MCF-7 breast cancer cells, not on nuclei where most other steroid receptors are located.
Biological Activity
Digestive gland subcellular fractions readily converted P4 into 5-pregnane-3,20-dione and minor amounts of a second metabolite and then 5-pregnane-3,20-dione was further metabolized to 3-hydroxy-5-pregnane-20-one (3,20-one) by 3β-HSD. This reaction was significantly inhibited by trilostane which is a 3β-HSD inhibitor[1-2].
References
[1] Dimastrogiovanni G, et al. Progesterone is actively metabolized to 5-pregnane-3,20-dione and 3-hydroxy-5-pregnan-20-one by the marine mussel Mytilus galloprovincialis. Aquatic Toxicology, 2015; 73-100.
[2] Ankley G, et al. Effects?of?progesterone?on?sperm motility?in?fathead?minnow. Aquatic Toxicology, 2011; 104: 121-125.
Properties of 5α-Pregnane-3,20-dione
Melting point: | 200 °C |
Boiling point: | 429.2±38.0 °C(Predicted) |
Density | 1.048±0.06 g/cm3(Predicted) |
storage temp. | Sealed in dry,Room Temperature |
solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
form | Solid |
color | White to Off-White |
InChI | InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14?,16-,17+,18-,19-,20-,21+/m0/s1 |
CAS DataBase Reference | 566-65-4(CAS DataBase Reference) |
NIST Chemistry Reference | 3,20-Allopregnanedione(566-65-4) |
Safety information for 5α-Pregnane-3,20-dione
Computed Descriptors for 5α-Pregnane-3,20-dione
InChIKey | XMRPGKVKISIQBV-CVHNGYJVSA-N |
SMILES | C1(=O)CC2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)[C@@H](C(=O)C)CC3)CC2 |
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