Basic information Description In vitro Safety Supplier Related
ChemicalBook >  Product Catalog >  Inorganic chemistry >  Inorganic salts >  Hydrides, nitrides, azides >  Hydride >  5α-Pregnane-3,20-dione

5α-Pregnane-3,20-dione

Basic information Description In vitro Safety Supplier Related

5α-Pregnane-3,20-dione Basic information

Product Name:
5α-Pregnane-3,20-dione
Synonyms:
  • 5-Alpha-Dihydro Progesterone-d8
  • Pregnane-3,20-dlone
  • ALLOPREGNANE-3,20-DIONE
  • ALLOPREGNAN-3,20-DIONE
  • ALLOPREGNANDIONE
  • (5S,8R,9S,10S,13S,14S,17S)-17-ACETYL-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE
  • 5 A-PREGNANE-3 20-DIONE
  • 5A-PREGNAN-3,20-DIONE
CAS:
566-65-4
MF:
C21H32O2
MW:
316.48
EINECS:
209-297-3
Product Categories:
  • Steroids
  • 566-65-4
Mol File:
566-65-4.mol
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5α-Pregnane-3,20-dione Chemical Properties

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
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
CAS DataBase Reference
566-65-4(CAS DataBase Reference)
NIST Chemistry Reference
3,20-Allopregnanedione(566-65-4)
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Safety Information

WGK Germany 
3
RTECS 
TU4157150
HS Code 
2937.29.9095

MSDS

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5α-Pregnane-3,20-dione Usage And Synthesis

Description

5α-Dihydroprogesterone (5α-DHP), also known as 5α-Pregnane-3,20-dione, is an endogenous progestogen and neurosteroid that is synthesized from progesterone. It is also an intermediate in the synthesis of allopregnanolone and isopregnanolone from progesterone. It is one of the mainly metabolites of progesterone in the digestive gland, the other tentatively identified as3β-hydroxy-5α-pregnan-20-one[1].

In vitro

5a-Pregnane-3,20-dione decreases cell-substrate attachment, adhesion plaques, vinculin expression, and polymerizes F-actin in MCF-7 breast cancer cells.

Uses

(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.

5α-Pregnane-3,20-dioneSupplier

Jiangsu Jiaerke Pharmaceuticals Group Corp., Ltd. Gold
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