Decreased rate of metabolism induced by a shift of the double bond in prostaglandin F 2alpha from the delta5 to the delta4 position.
The synthesis of an isomer of prostaglandin F 2alpha,9alpha,11alpha,15(S)-trihydroxyprosta-4-cis,13-transdienoic acid is described. The metabolism of this compound in the rat has been investigated. The rate of degradation by beta-oxidation was slowed down considerably. Thus 10-20% of the injected isomer was excreted in the urine unchanged indicating a longer half-life in the circulation than for prostaglandin F 2alpha. More over 2% was excreted as C20 metabolites, 11-18% as C18 metabolites and 8-15% as C16 metabolites. This relative resistance to degradation by beta-oxidation is of considerable biochemical and pharmacological interest.
D000818:Animals; D007536:Isomerism; D008297:Male; D013058:Mass Spectrometry; D011460:Prostaglandins F / Q000138:chemical synthesis / Q000378:metabolism; D011461:Prostaglandins F, Synthetic; D051381:Rats; D013329:Structure-Activity Relationship
D011460:Prostaglandins F; D011461:Prostaglandins F, Synthetic