title: Stereoselective hydrolysis of O-acetyl propranolol as prodrug in human serum.
abstract: A direct high-performance liquid chromatographic method was developed for the assays of the enantiomers of O-acetyl propranolol. Using this procedure, the stereochemical characteristics on hydrolysis of racemic O-acetyl propranolol as a prodrug have been studied in phosphate buffer (pH 7.4) and in 90% human serum. In the phosphate buffer, no difference in the hydrolysis rate between the esters of (R)- and (S)-propranolol was observed. In 90% human serum, the hydrolysis of the esters was accelerated, and the hydrolysis rate of the ester of (R)-isomer was about three times faster than that of the ester of (S)-isomer. The interconversion between (R)- and (S)-isomer was not observed during the hydrolysis of prodrug in buffer and in human serum. These results indicated that hydrolysis of O-acetyl propranolol occurs stereoselectively in human serum.
authors.affiliation: Faculty of Pharmaceutical Sciences, Mukogawa Women's University, Hyogo, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Takahashi
authors.forename: J
authors.initials: J
authors.lastname: Haginaka
authors.forename: S
authors.initials: S
authors.lastname: Tamagawa
authors.forename: T
authors.initials: T
authors.lastname: Nishihata
authors.forename: H
authors.initials: H
authors.lastname: Yasuda
authors.forename: T
authors.initials: T
authors.lastname: Katagi
mesh_terms: D002851:Chromatography, High Pressure Liquid; D006801:Humans; D006868:Hydrolysis; D007700:Kinetics; D011355:Prodrugs; D011433:Propranolol / Q000031:analogs & derivatives* / Q000097:blood; D013237:Stereoisomerism
chemical_list: D011355:Prodrugs; C066044:O-acetylpropranolol; D011433:Propranolol