Gastroprotective effect of stereoisomeric cis- and trans-2-(1-pyrrolidinyl) and 2-(1-pyrrolidinylmethyl)cyclohexyl alkoxycarbanilates in rats.

The effect of cis- and trans-isomers of 2-(1-pyrrolidinyl) and of 2-(1-pyrrolidinylmethyl)cyclohexyl alkoxycarbanilates was tested in acute gastric injury induced by phenylbutazone and/or 96% ethanol administration in rats. In both models a more pronounced antiulcer and gastroprotective activity was observed after pretreatment with the trans-isomer of 2-(1-pyrrolidinyl)cyclohexyl ester of 3(n)-pentyloxycarbanilic acid. Its cis-isomer, by comparison, was less effective against ethanol-induced gastric injury and failed to prevent the gastric damage induced by phenylbutazone. After introducing a methylene group into the hydrophilic part of the molecule, there was a loss of stereospecific difference, with both stereoisomers exerting a similar gastroprotective activity.