ChemicalBook > CAS DataBase List > 5α-Pregnane-3,20-dione

5α-Pregnane-3,20-dione

Description In vitro

Product Name: 5α-Pregnane-3,20-dione
CAS No.: 566-65-4
Chemical Name: 5α-Pregnane-3,20-dione
Synonyms: Pregnane-3,20-dione;5α-dihydroprogesterone;5α-pregnane-3,20-dione;ALLOPREGNANDIONE;Allopregnanedione;Pregnane-3,20-dlone;Estrone Impurity 23;5A-PREGNAN-3,20-DIONE;ALLOPREGNAN-3,20-DIONE;5A-DIHYDROPROGESTERONE
CBNumber: CB0377209
Molecular Formula: C21H32O2
Formula Weight: 316.48
MOL File: 566-65-4.mol

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5α-Pregnane-3,20-dione Property

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

WGK Germany: 3
RTECS: TU4157150
HS Code: 2937.29.9095

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: R197009
Product name: 5-ALPHA-PREGNANE-3,20-DIONE
Purity: Aldrich<sup>CPR</sup>
Packaging: 1 unit
Price: $143
Updated: 2025/07/31

Sigma-Aldrich

Product number: P7754
Product name: 5α-Pregnane-3,20-dione (allo)
Purity: progesterone metabolite
Packaging: 1g
Price: $335
Updated: 2025/07/31

Sigma-Aldrich

Product number: R197009
Product name: 5-ALPHA-PREGNANE-3,20-DIONE
Purity: AldrichCPR
Packaging: 1MG
Price: $139
Updated: 2024/03/01

Sigma-Aldrich

Product number: P7754
Product name: 5α-Pregnane-3,20-dione (allo)
Purity: progesterone metabolite
Packaging: 500mg
Price: $175
Updated: 2024/03/01

TCI Chemical

Product number: P2423
Product name: 5α-Pregnane-3,20-dione
Packaging: 1G
Price: $62
Updated: 2025/07/31

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5α-Pregnane-3,20-dione Chemical Properties,Usage,Production

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].

IC 50

Human Endogenous Metabolite

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 5α-Pregnane-3,20-dione manufacturers

Wuhan Biocar Pharmacy CO.,Ltd.

Product: Pregnane-3,20-dlone 566-65-4
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 2000kg
Release date: 2025-02-27

Shaanxi Xianhe Biotech Co., Ltd

Product: Pregnane-3,20-dione 566-65-4
Price: US $0.00/KG
Min. Order: 1KG
Purity: 0.99
Supply Ability: 1000KG
Release date: 2025-04-17

Wuhan Han Sheng New Material Technology Co.，Ltd

Product: 5-alpha-Dihydroprogesterone 566-65-4
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 50tons
Release date: 2023-08-24

566-65-4, 5α-Pregnane-3,20-dioneRelated Search:

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

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

5ALPHA-PREGNANE-3,20-DIONE (ALLO)

5ALPHA-DIHYDROPROGESTERONE

5-ALPHA-PREGNAN-3,20-DIONE

5A-DIHYDROPROGESTERONE

(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

5α-pregnane-3,20-dione (allo)

(5S,8R,9S,10S,13R,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

4-07-00-02199 (Beilstein Handbook Reference)

5 A-PREGNANE-3 20-DIONE 99%

5α-Pregnan-3,20-dione-1,2,4,5,6,7-D6

5α-Dihydroprogesterone, Allopregnane-3,20-dione

(5S,8R,9S,10S,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

Allopregnanedione

ALLOPREGNENDIONE(RG)(CALL)

5α-Pregnane-3,20-dione (allo),5α-Dihydroprogesterone, Allopregnane-3,20-dione

Hydrogenated progesterone

5alpha-Pregnane-3,20-dione (allo) progesterone metabolite

(8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

(8R,9S,10S,13S,14S,17S)-17-ethanoyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

Pregnane-3,20-dione, (5α)-

5α-pregnane-3,20-dione

PREGNANE-3,20-DIONE CAS NO 566-65-4

5-alpha-Dihydroprogesterone ISO 9001：2015 REACH

Estrone Impurity 23

566-65-4 5-alpha-Dihydroprogesterone

5a-Pregnane-3,20-Dione（Dihydroprogesterone）

(5S,8R,9S,10S,13S,14S,17S)-17-Acetyl-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Pregnenolone Impurity 13

5α-PREGNAN-3, 20-DIONE

Allodihydroprogesterone

5a-Pregnane-3,20-dione, 10 mM in DMSO

566-65-4

Steroids

566-65-4