Phenytoin-lipid conjugates as potential prodrugs of phenytoin.
Phenytoin-1-triglycerides and phenytoin-2-triglycerides were synthesized as potential prodrugs of phenytoin by covalent binding of 3-hydroxymethylphenytoin by succinic acid to the positions 1 and 2 of diglycerides, respectively. The corresponding 1- and 2-monoglycerides were prepared. In addition, replacement of glycerol by 3-hydroxy-2-hydroxymethylpropionic acid furnished lipids that allowed direct coupling of 3-hydroxymethylphenytoin. The lipid conjugates proved to be substrates for pancreatic lipase in vitro.
Scriba
G K
GK
Department of Pharmaceutical Chemistry, University of Münster, Germany.
D000818:Animals; D008049:Lipase / Q000378:metabolism; D008055:Lipids / Q000737:chemistry*; D010179:Pancreas / Q000201:enzymology; D010672:Phenytoin / Q000737:chemistry*; D011355:Prodrugs / Q000138:chemical synthesis*; D013552:Swine; D014280:Triglycerides
D008055:Lipids; D011355:Prodrugs; D014280:Triglycerides; D010672:Phenytoin; D008049:Lipase