64318-79-2 Usage
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 64318-79-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,3,1 and 8 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 64318-79:
(7*6)+(6*4)+(5*3)+(4*1)+(3*8)+(2*7)+(1*9)=132
132 % 10 = 2
So 64318-79-2 is a valid CAS Registry Number.
InChI:InChI=1/C23H38O5/c1-5-6-15-23(2,3)21(26)14-13-18-17(19(24)16-20(18)25)11-9-7-8-10-12-22(27)28-4/h10,12-14,17-18,20-21,25-26H,5-9,11,15-16H2,1-4H3/b12-10+,14-13-/t17-,18-,20-,21+/m0/s1
64318-79-2Relevant articles and documents
Prostaglandin analogues
-
, (2008/06/13)
New trans-Δ2 -prostaglandins of the formula STR1 (wherein R1 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 10 carbon atoms, R2 represents a 1,1-dimethyl-pentyl group or a 2-ethylheptyl group, the wavy line indicates attachment of the depicted group in α-configuration or racemic form consisting of equimolecular mixtures of α-configuration and β-configuration and the C2 -C3 and C13 -C14 double bonds are trans), which are useful for the treatment of hypertension, contraception menstrual regulation.
