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Journal of Pharmacology And Experimental Therapeutics, Vol. 113, Issue 3, 272-282, 1955
Copyright © 1955 by American Society for Pharmacology and Experimental Therapeutics

RELATIONSHIP BETWEEN STRUCTURE AND IN VITRO METABOLISM OF VARIOUS ESTERS AND AMIDES IN HUMAN SERUM

RUTH MITCHELL LEVINE 1 and BYRON B. CLARK 1

1 Department of Pharmacology, Tufts College Medical School, Boston, Massachusetts

Substituting an amide linkage for an ester linkage completely stabilizes the compound to hydrolysis by human serum.

The stability of an ester, in human serum, can be increased: a) by substitution on the agr-carbon of the alcohol; b) the agr-carbon of the acid ; c) by increasing the length of the alcohol chain from 2 to 3 carbon atoms ; and d) by increasing the size of the substituent group on the terminal nitrogen.

The stability of a tertiary amine ester can be decreased by forming the corresponding quaternary compound.

Submitted on October 29, 1954






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Copyright © 1955 by the American Society for Pharmacology and Experimental Therapeutics.