Glycerides as prodrugs. 1. Synthesis and antiinflammatory activity of 1,3-bis(alkanoyl)-2-(O-acetylsalicyloyl)glycerides (aspirin triglycerides).
A series of 1,3-bis(alkanoyl)-2-(O-acetylsalicyloyl)glycerides (aspirin triglycerides) having aspirin at the 2 position of glycerol and fatty acids at the 1 and 3 positions was prepared. The compounds were administered orally and tested for efficacy in the rat paw edema test, and the stomachs were examined for the presence of lesions. The results showed that the members of this series in which the fatty acids are of intermediate chain length (C4-C12) do not cause gastric lesions and have essentially all the systemic activity associated with aspirin.
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis; D001241:Aspirin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002351:Carrageenan; D004305:Dose-Response Relationship, Drug; D004487:Edema / Q000139:chemically induced / Q000503:physiopathology; D008297:Male; D051381:Rats; D012459:Salicylates / Q000097:blood; D013276:Stomach Ulcer / Q000139:chemically induced; D013329:Structure-Activity Relationship; D013997:Time Factors; D014280:Triglycerides / Q000138:chemical synthesis* / Q000494:pharmacology
D000893:Anti-Inflammatory Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D012459:Salicylates; D014280:Triglycerides; D002351:Carrageenan; D001241:Aspirin