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)

Safety Information

WGK Germany 

3

RTECS 

TU4157150

HS Code 

2937.29.9095

MSDS

• Language:English Provider:5-alpha-Dihydroprogesterone
• Language:English Provider:SigmaAldrich

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-dione(566-65-4)Related Product Information

• Ecdysone
• Pregnenolone
• Gestrinone
• Progesterone
• Gestodene
• Diethylstilbestrol
• Medroxyprogesterone Acetate
• 16-Dehydroprogesterone
• Dehydroepiandrosterone
• 5A-PREGNAN-21-OL-3-20-DIONE CRYSTALLINE
• 5-ALPHA-DIHYDROCORTISONE
• 5-ALPHA-DIHYDROCORTICOSTERONE
• 17-ALPHA-HYDROXY-5-ALPHA-PREGNANE-3,20-DIONE
• 5-ALPHA-DIHYDRO SUBSTANCE 'S'
• ALLOPREGNANETRIONE
• Allopregnane-3,6,20-trione
• 11-BETA,17-ALPHA,21-TRIHYDROXY-5-ALPHA-PREGNANE-3,20-DIONE
• 17,21-dihydroxy-5alpha-pregnane-3,11,20-trione 21-acetate