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5α-Dihydroprogesterone

Names

[ CAS No. ]:
566-65-4

[ Name ]:
5α-Dihydroprogesterone

[Synonym ]:
5a-Dihydroprogesterone
4-07-00-02199 (Beilstein Handbook Reference)
Pregnane-3,20-dione, (5-α)- (9CI)
5alpha-Pregnan-3,20-dione
MFCD00067132
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
UNII:98G4S1OH0Z
5α-pregnane-3,20-dione
(5α)-Pregnane-3,20-dione
Pregnane-3,20-dione
5α-dihydroprogesterone
EINECS 209-297-3
Allopregnan-3,20-dione
3,20-Allopregnanedione
5alpha-pregnane-3,20-dione
3,20-Dioxo-5a-pregnane
5a-Pregnan-3,20-dione
Pregnane-3,20-dione, (5α)-
Pregnane-3,20-dione, (5α)- (9CI)
3,20-Dioxo-5alpha-pregnane
5-α-pregnane-3,20-dione
allopregnandione
5alpha-Dihydroprogesterone
5a-Pregnane-3,20-dione
5α-Pregnane-3,20-dione (8CI)
(5Alpha)-Pregnane-3,20-dione

Biological Activity

[Description]:

5a-Pregnane-3,20-dione is the endogenous progesterone metabolite.

[Related Catalog]:

Research Areas >> Endocrinology
Natural Products >> Flavonoids

[Target]

Human Endogenous Metabolite


[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[1].

[References]

[1]. Wiebe JP, et al. The endogenous progesterone metabolite, 5a-pregnane-3,20-dione, decreases cell-substrate attachment, adhesion plaques, vinculin expression, and polymerized F-actin in MCF-7 breast cancer cells. Endocrine. 2001 Oct;16(1):7-14.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
429.2±38.0 °C at 760 mmHg

[ Melting Point ]:
204 °C

[ Molecular Formula ]:
C21H32O2

[ Molecular Weight ]:
316.478

[ Flash Point ]:
160.3±23.8 °C

[ Exact Mass ]:
316.240234

[ PSA ]:
34.14000

[ LogP ]:
4.31

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.516

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TU4157150
CHEMICAL NAME :
5-beta-Pregnane-3,20-dione
CAS REGISTRY NUMBER :
566-65-4
BEILSTEIN REFERENCE NO. :
2058506
LAST UPDATED :
199709
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C21-H32-O2
MOLECULAR WEIGHT :
316.53
WISWESSER LINE NOTATION :
L E5 B666 OVTJ A1 E1 FV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 11,117,1968
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 11,117,1968

Safety Information

[ Hazard Codes ]:
Xi

[ WGK Germany ]:
3

[ RTECS ]:
TU4157150

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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