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HomeProduct name list5α-Pregnane-3,20-dione

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
5α-Pregnane-3,20-dione Structural

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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