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5α-Pregnane-3,20-dione

5α-Pregnane-3,20-dione structure

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;5A-DIHYDROPROGESTERONE;ALLOPREGNAN-3,20-DIONE

CBNumber:: CB0377209

Molecular Formula:: C21H32O2

Molecular Weight:: 316.48

MDL Number:: MFCD00067132

MOL File:: 566-65-4.mol

Last updated:2025-04-17 18:22:24

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5α-Pregnane-3,20-dione 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)
EWG's Food Scores	1
FDA UNII	98G4S1OH0Z
NIST Chemistry Reference	3,20-Allopregnanedione(566-65-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS07,GHS08
Signal word	Warning
Hazard statements	H312-H302-H332-H351-H361fd
Precautionary statements	P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501-P201-P202-P281-P308+P313-P405-P501-P261-P271-P304+P340-P312
WGK Germany	3
RTECS	TU4157150
HS Code	2937.29.9095

5α-Pregnane-3,20-dione price More Price(26)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	R197009	5-ALPHA-PREGNANE-3,20-DIONE AldrichCPR	566-65-4	1MG	$139	2024-03-01	Buy
Sigma-Aldrich	P7754	5α-Pregnane-3,20-dione (allo) progesterone metabolite	566-65-4	500mg	$175	2024-03-01	Buy
Sigma-Aldrich	P7754	5α-Pregnane-3,20-dione (allo) progesterone metabolite	566-65-4	1g	$313	2024-03-01	Buy
TCI Chemical	P2423	5α-Pregnane-3,20-dione	566-65-4	1G	$62	2024-03-01	Buy
TCI Chemical	P2423	5α-Pregnane-3,20-dione	566-65-4	5G	$305	2024-03-01	Buy

Product number	Packaging	Price	Buy
R197009	1MG	$139	Buy
P7754	500mg	$175	Buy
P7754	1g	$313	Buy
P2423	1G	$62	Buy
P2423	5G	$305	Buy

5α-Pregnane-3,20-dione Chemical Properties,Uses,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 synthesis

Synthesis of 5α-Pregnane-3,20-dione from ALLOPREGNANOLONE

5α-Pregnane-3,20-dione Preparation Products And Raw materials

Raw materials

PREGNANEDIONE Progesterone

Preparation Products

Pregnan-20-one, 3-hydroxy-3-methyl-, (3β,5α)- GANAXOLONE Pregnan-20-one, (5alpha)-

5α-Pregnane-3,20-dione Suppliers

Global( 176)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Pharmaceuticals Group Corp., Ltd.	+8613004379774	wu@jiaerke.com	China	33	58
Wuhan Han Sheng New Material Technology Co.，Ltd	+8617798174412	admin01@hsnm.com.cn	China	2097	58
Nanjing Shizhou Biotechnology Co., Ltd	+86-15850508050 +86-15850508050	sean.lv@synzest.com	China	323	58
Nantong Guangyuan Chemicl Co,Ltd	+undefined17712220823	admin@guyunchem.com	China	615	58
Shaanxi Xianhe Biotech Co., Ltd	+8617709210191	Jerry@xhobio.com	China	884	58
Capot Chemical Co.,Ltd.	+86-（0）57185586718 +86-13336195806	sales@capot.com	China	29730	60
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-+86-371-66670886	info@dakenam.com	China	19805	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21628	55
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29858	58
Hubei xin bonus chemical co. LTD	86-13657291602	linda@hubeijusheng.com	CHINA	22963	58

Supplier	Advantage
Pharmaceuticals Group Corp., Ltd.	58
Wuhan Han Sheng New Material Technology Co.，Ltd	58
Nanjing Shizhou Biotechnology Co., Ltd	58
Nantong Guangyuan Chemicl Co,Ltd	58
Shaanxi Xianhe Biotech Co., Ltd	58
Capot Chemical Co.,Ltd.	60
Shanghai Daken Advanced Materials Co.,Ltd	58
Henan Tianfu Chemical Co.,Ltd.	55
career henan chemical co	58
Hubei xin bonus chemical co. LTD	58

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

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2025-04-27	Pregnane-3,20-dlone 566-65-4	US $0.00-0.00 / kg	1kg	99%	2000kg	Wuhan Biocar Pharmacy CO.,Ltd.
2025-04-24	Pregnane-3,20-dione 566-65-4	US $0.00 / KG	1KG	0.99	1000KG	Shaanxi Xianhe Biotech Co., Ltd
2025-03-21	5-Alpha-Dihydroprogesterone 566-65-4	US $0.00 / KG	1KG	99%	50000KG/month	Hebei Mujin Biotechnology Co.,Ltd

Pregnane-3,20-dlone
566-65-4
US $0.00-0.00 / kg
99%
Wuhan Biocar Pharmacy CO.,Ltd.

Pregnane-3,20-dione
566-65-4
US $0.00 / KG
0.99
Shaanxi Xianhe Biotech Co., Ltd

5-Alpha-Dihydroprogesterone
566-65-4
US $0.00 / KG
99%
Hebei Mujin Biotechnology Co.,Ltd

566-65-4(5α-Pregnane-3,20-dione)Related Search:

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1of4

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, (5alpha)- 5A-pregnane-3-20-dione-allo 5alpha-Pregnan-3,20-dione-1,2,4,5,6,7-D6 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 5-Alpha-Dihydro Progesterone-d8 Pregnane-3,20-dlone Pregnane-3,20-dione, (5α)- 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 Pregnane-3,20-dione 5α-dihydroprogesterone 5α-pregnane-3,20-dione 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