Anti-inflammatory/anti-pyretic salicylic acid esters with low gastric ulcerogenic activity

Agents Actions. 1980 Nov;10(5):451-6. doi: 10.1007/BF01968046.

Abstract

The methyl and some other esters of acetylsalicylic and salicylic acids and their derivatives were found to have much lower gastric ulcerogenic activity (when assayed in the stress-sensitized rat) compared with their corresponding acids. There was little or no loss in therapeutic potencies of these salicylate esters as determined by assessment of anti-inflammatory activity (against the carrageenan-induced oedema) and antipyretic activity (against yeast-induced fever in rats. The methyl ester of acetylsalicylic acid (=AME) was almost devoid of gastric irritancy/ulcerogenicity (as observed with acetylsalicylic acid) when given orally to pigs for 10 days. AME had appreciable anti-inflammatory activity in the adjuvant-arthritis model and at high doses (200 mg/kg t.i.d.) was without the lethal effects seen with acetylsalicylic acid. Moreover, no toxic effects were seen after long-term administration of 100-1000 mg/kg/day AME for 3-4 months. The results provide further evidence for the hypothesis that the carboxylic acid moiety of salicylates is a major factor in the gastric ulcerogenic activity of these drugs. The methyl esters of these salicylates may be considered as models for the development of pro-drugs and in some cases may be therapeutic alternatives to acetylsalicylic acid or salicylate.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / toxicity*
  • Anti-Inflammatory Agents, Non-Steroidal / toxicity*
  • Aspirin / analogs & derivatives*
  • Aspirin / toxicity
  • Drug Evaluation, Preclinical
  • Female
  • Male
  • Rats
  • Salicylates / toxicity*
  • Stomach Ulcer / chemically induced*
  • Structure-Activity Relationship
  • Swine

Substances

  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Salicylates
  • Aspirin