Synthesis and biological activity of 9-deoxo-9-methylene and related prostaglandins.
A number of PGE analogs have been synthesized in which the C-9 carbonyl group has been replaced by an exo-methylene group. These chemically stable 9-deoxo-9-methylene-PGEs exhibit biological profiles very similar to their less stable PGE relatives. 9-Deoxo-16,16-dimethyl-9-methylene-PGE2 (7) retains the useful uterine-stimulating potency of 16,16-dimethyl-PGE2 but is approximately 300 times less enteropooling in the rat. In preliminary clinical trials, 7 has shown efficacy for pregnancy termination by the oral and vaginal routes of administration, as well as relative freedom from gastrointestinal side effects.
D015064:16,16-Dimethylprostaglandin E2 / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001681:Biological Assay; D001794:Blood Pressure / Q000187:drug effects; D006224:Cricetinae; D005260:Female; D005750:Gastric Juice / Q000187:drug effects / Q000378:metabolism; D005769:Gastrointestinal Motility / Q000187:drug effects; D005849:Gerbillinae; D008722:Methods; D010974:Platelet Aggregation / Q000187:drug effects; D011459:Prostaglandins E, Synthetic / Q000138:chemical synthesis*; D051381:Rats; D013329:Structure-Activity Relationship; D014590:Uterine Contraction / Q000187:drug effects
D011459:Prostaglandins E, Synthetic; C025505:meteneprost; D015064:16,16-Dimethylprostaglandin E2