Synonyms:

17-Hydroxypregn-4-en-3,20-dione;
17-hydroxy-pregn-4-ene-20-dione;
17-hydroxypregn-4-ene-3,20-dione;
delta(4)-pregnene-17alpha-ol-3,20-dione;
gestagenogador;
prodix;
prodox;
(8R,9S,10R,13S,14S,17R)-17-ACETYL-17-HYDROXY-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE
17A-HYDROXY-4-PREGNENE-3,20-DIONE
17a-hydroxypregn-4-ene-3,20-dione
17A-HYDROXYPROGESTERONE
17ALPHA-HYDROXY-4-PREGNENE-3,20-DIONE
17-ALPHA-HYDROXYPREGN-4-ENE-3,20-DIONE
17ALPHA-HYDROXYPROGESTERONE
17-HYDROXYPROGESTERONE
4-PREGNEN-17ALPHA-OL-3,20-DIONE
4-pregnen-17a-ol-3,20-dione

4-PREGNEN-17-OL-3,20-DIONE
(8R,9S,10R,13S,14S,17R)-17-ACETYL-17-HYDROXY-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE
HYDROXYPROGESTERONE
HYDROXYPROGESTERONE, 17A-
17-Hydroxypregn-4-en-3,20-dione
17-hydroxy-pregn-4-ene-20-dione
17-hydroxypregn-4-ene-3,20-dione

delta(4)-pregnene-17alpha-ol-3,20-dione
gestagenogador
prodix
prodox

CAS:

68-96-2

MF:

C21H30O3

MW:

330.46

EINECS:

200-699-4

Product Categories:

Inhibitors;
MIRADON;
Steroids;
Biochemistry;
Hydroxyketosteroids;

Intermediates & Fine Chemicals;
Pharmaceuticals

Mol File:

Melting point 

276°C

Boiling point 

407.89°C (rough estimate)

density 

1.0998 (rough estimate)

refractive index 

90 ° (C=1, CHCl3)

Fp 

9℃

storage temp

-20C Freezer

pka

13.03±0.60(Predicted)

form 

neat

Water Solubility 

5.056mg/L(20 ºC)

Merck 

14,4839

BRN 

3218109

CAS DataBase Reference

NIST Chemistry Reference

Hazard Codes 

Risk Statements 

Safety Statements 

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

RTECS 

TU5060000

HS Code 

38220090

Hazardous Substances Data

Chemical Properties

White Solid

Originator

Prodox,Upjohn

Uses

Progesteron. It was isolated from adrenal glands.

Uses

anticoagulant

Uses

17α-Hydroxy Progesterone is a metabolite of Progesterone. It was isolated from adrenal glands.

Definition

ChEBI: A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.

Indications

Hydroxyprogesterone has been used prophylactically for the 12th to 37th week of pregnancy, particularly in women who are in the high-risk category for premature delivery (e.g., those with a history of premature delivery or spontaneous abortion).
A concern relating to teratogenic potential has limited its use.
Hydroxyprogesterone as a tocolytic agent requires further evaluation before its routine prophylactic administration can be recommended.

Manufacturing Process

A suspension of 90.0 g of δ5-pregnen-3β,17α-diol-20-one in 2300 ml of 85% formic acid was shaken for 2 h at a temperature of 70C. During this time the compound partially dissolved and at the same time a new crystalline substance appeared in the solution. After cooling, the precipitate was filtered, thus giving 80.0 g of the 3-formate of δ5-pregnen-3β,17α-diol-20-one having a melting point of 204°-207°C.

5.0 g of the 3-formate of δ5-pregnen-3β,17α-diol-20-one suspended in 120 ml of acetic anhydride was treated with 1.5 g of p-toluenesulfonic acid and the mixture was stirred for 9 h at room temperature.
It was poured into water and after 2 h standing, the precipitate was filtered and washed to neutral, thus yielding the 3-formate 17-acetate of δ5-pregnen-3β,17α-diol-20-one in a yield of over 90%.
1.0 g of 3-formate 17-acetate of δ5-pregnen-3β,17α-diol-20-one was dissolved in 30 ml of xylene and 10 ml of cyclohexanone and 4 ml of the solution were distilled in order to remove traces of moisture. 1.0 g of aluminum isopropylate was added to the hot solution and the mixture was refluxed for 45 min.
After cooling to 90°C, water was added and the organic solvents were removed by steam distiliation.
Salt was added to the aqueous suspension and the residue was filtered, dried and extracted with hot acetone.
The acetone solution was evaporated to dryness and the residue was crystallized from chloroformmethanol, thus giving 610.0 mg of the 17-acetate of δ4-pregnen-17α-ol-3,20- dione (17-acetoxy-progesterone) with a melting point of 239°-240°C.
Saponification of this compound with 1% methanolic potassium hydroxide yielded 80% of δ4-pregnen-17α-ol-3,20-dione.

Therapeutic Function

Progestin

Raw materials

Preparation Products