gemeprost Chemical Properties

Boiling point:

438.73°C (rough estimate)

Density 

1.0380 (rough estimate)

refractive index 

1.5800 (estimate)

pka

13.84±0.60(Predicted)

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

gemeprost Usage And Synthesis

Description

Gemeprost, a metabolically stabilized analog of PGE1, has been demonstrated to reliably induce termination of early pregnancy when administered as a vaginal suppository. Its effect is presumably due to both uterine contraction and rapid decline of steroid hormone levels. Minimal side effects have been reported.

Originator

Ono (Japan)

Uses

Gemeprost is an analogue of Prostaglandin (P838600). Gemeprosts, similarly to Nitric Oxide donors, induce uterine cervical dilation and are used before surgical termination of pregnancy.

Uses

Prostaglandin.

Definition

ChEBI: Gemeprost is an aliphatic alcohol.

Manufacturing Process

Synthesis of 9-oxo-1α,15α-bis-(2-tetrahydropyranyloxy)-16,16-dimethylprosta-trans-2, trans-13-dienoic acid: 4 g of ethyl 9α-hydroxy-11α15α-bis-(2- tetrahydropyranyloxy)-16,16-dimethyl-prosta-trans-2,trans-13-dienoate were dissolved in 130 ml of a mixture of ethanol-water (3:1), mixed with 3.9 g of potassium hydroxide and stirred at 25°C for 2 hours. The reaction mixture was acidified with aqueous solution of oxalic acid to pH 5, and diluted with 100 ml of water, extracted with ethyl acetate. The extracts were washed with water, dried over sodium sulfate and concentrated under reduced pressure to obtain 3.88 g of 9α-hydroxy-11α,15α-bis-(2-tetrahydropyranyloxy)-16,16- dimethyl-prosta-trans-2,trans-13dienoic acid.
The obtained compound 2.46 g were dissolved in 72 ml of diethyl ether and stirred at 3°C. To which a solution of manganese sulfate (15 g), 3.1 g of chromium trioxide, 72 ml of water and 3.5 ml of sulfuric acid was added. After stirring for 3.5 hours at 3°C, extracted with diethyl ether. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-benzene (1:1) as eluent to give 2.35 g of the title compound.
Synthesis of 16,16-dimethyl-trans-δ2-PGE1: 2.35 g of the bistetrahydropyranyl ether were dissolved in 6 ml of tetrahydrofuran and 60 ml of 65%-acetic acid aqueous solution and the solution stirred at 60°C to 70°C for 20 minutes. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-cyclohexane (2:3) as eluent to yield 270 mg of the title compound.

brand name

CERVAGEM

Therapeutic Function

Prostaglandin, Cervical softener

gemeprost(64318-79-2)Related Product Information

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