| Identification | More | [Name]
5-alpha-Dihydroprogesterone | [CAS]
566-65-4 | [Synonyms]
5A-DIHYDROPROGESTERONE
5ALPHA-DIHYDROPROGESTERONE
5-ALPHA-PREGNAN-3,20-DIONE
5ALPHA-PREGNANE-3,20-DIONE (ALLO)
5A-PREGNAN-3,20-DIONE
5 A-PREGNANE-3 20-DIONE
(5S,8R,9S,10S,13S,14S,17S)-17-ACETYL-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE
ALLOPREGNAN-3,20-DIONE
ALLOPREGNANDIONE
ALLOPREGNANE-3,20-DIONE
(5-alpha)-pregnane-20-dione
3,20-Allopregnanedione
3,20-Dioxo-5alpha-pregnane
5alpha-Pregnane-3,20-dione
5-beta-pregnane-3,20-dione
Pregnane-3,20-dione
Pregnane-3,20-dione, (5alpha)-
5A-pregnane-3-20-dione-allo
5alpha-Pregnan-3,20-dione-1,2,4,5,6,7-D6
5α-dihydroprogesterone | [EINECS(EC#)]
209-297-3 | [Molecular Formula]
C21H32O2 | [MDL Number]
MFCD00067132 | [Molecular Weight]
316.48 | [MOL File]
566-65-4.mol |
| Questions And Answer | Back Directory | [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. |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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: A C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone. | [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]. | [IC 50]
Human Endogenous Metabolite | [storage]
Store at -20°C | [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. |
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