16669-06-0

Usage

Uses

Used in Pharmaceutical Industry:
2-((8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)acetonitrile is used as a progestogen in the pharmaceutical industry. It is an impurity of Dienogest, which is a synthetic progestin used in combination with estrogen as an oral contraceptive. Dienogest helps regulate the menstrual cycle and prevents ovulation, making it an essential component in birth control pills.

Upstream product

• 65928-58-7 Dienogest 
• 67473-36-3 17α-Cyanomethyl-17β-hydroxyestr-4-en-3-one 

Relevant academic research and scientific papers

Nitrile hydratase from Rhodococcus erythropolis: Metabolization of steroidal compounds with a nitrile group

The progestin dienogest (17α-cyanomethyl-17β-hydroxy-estra-4,9-dien-3-one) was metabolized by the nitrile hydratase-containing microorganism Rhodococcus erythropolis. An enzymatic hydrolysis of the nitrile group at the 17α-side chain was intended to obtain novel derivatives and to test them for progesterone receptor affinity. In contrast to the rapid enzymatic hydrolysis of nonsteroidal nitriles, the nitrile group of dienogest was cleaved very slowly. The dominant reaction was an aromatization of ring A. After prolonged fermentation, the 17α-acetamido derivatives of estradiol and of 9(11)-dehydroestradiol were formed. Three of the metabolites were also prepared synthetically. They were tested for hormonal activity by assessing their binding to progesterone and estrogen receptors in vitro. Neither the aromatized 17α-acetamido derivatives nor the dienogest derivative 17α-acetamido-17β-hydroxy-estra-4,9-dien-3-one, which was prepared synthetically only, exhibited affinity for the progesterone receptor. Copyright (C) 1999 Elsevier Science Inc.

MICROBIAL TRANSFORMATION OF 17α-CYANOMETHYL-17-HYDROXY-4,9-ESTRADIEN-3-ONE (STS 557) AND 17α-CYANOMETHYL-19-NORTESTOSTERONE BY MYCOBACTERIUM SMEGMATIS

Microbial transformation of the new progestagen STS 557 (17α-cyanomethyl-17-hydroxy-4,9-estradien-3-one) by Mycobacterium smegmatis yielded predominantly ring A-aromatized compounds. 17α-cyanomethyl-1,3,5(10),9(11)-estratetraene-3,17-diol, 17α-cyanomethyl-1,3,5(10)-estratriene-3,17-diol and the corresponding 3-methyl ethers.The analogous compound without the 9(10) double bound, 17α-cyanomethyl-19-nortestosterone, was transformed mainly to 5α-hydrogenated metabolites: 17α-cyanomethyl-17-hydroxy-5α-estran-3-one, 17α-cyanomethyl-17-hydroxy-5α-1-estren-3-one, 17α-cyanomethyl-5α-estrane-3α,17-diol, and 17α-cyanomethyl-5α-estrane- 3β,17-diol.From these results, it is concluded that 4,9-dien-3-oxo compounds are not substrates for enzymatic 5α-hydrogenation.