gemcitabine elaidate

Gemcitabine elaidate is a lipophilic prodrug of the antimetabolite nucleoside analog gemcitabine. It is formed by esterifying gemcitabine with elaidic (trans-unsaturated) fatty acid to enhance cellular uptake and prolong intracellular retention. Once inside the body or cell, it is converted back to active gemcitabine. The modification was designed to bypass resistance mechanisms related to low expression of the hENT1 transporter and improve efficacy in tumors with such resistance. Its mechanism of action mirrors that of gemcitabine—primarily as an antimetabolite and DNA synthesis inhibitor—leading to inhibition of tumor cell proliferation. Developed for solid tumors including non-small cell lung cancer and pancreatic cancer, its clinical development was discontinued after failing primary endpoints in phase II trials for metastatic pancreatic cancer[1][3][4][5].

Other names

Gemcitabine 5'-elaidic acid ester2'-Deoxy-2',2'-difluorocytidine 5'-(9E)-octadec-9-enoate5'-O-(trans-9"-octadecenoyl)-1-beta-D-2'deoxy-2',2'-difluorocytidine