Stereoselective metabolism of 3-isopropyl-5-(1-naphthoxymethyl)oxazolidine, a prodrug of propranolol.
This investigation suggests that the oxazolidine derivative of propranolol is a prodrug which is hydrolysed stereoselectively to propranolol by hepatic post-mitochondrial supernatant. The (S)-form of the prodrug is more stable in the biological system than its (R)-form.
Kamal
A
A
Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad.
Rao
A B
AB
Rao
M V
MV
D000818:Animals; D002021:Buffers; D002851:Chromatography, High Pressure Liquid; D006868:Hydrolysis; D008099:Liver / Q000378:metabolism*; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism*; D010080:Oxazoles / Q000737:chemistry / Q000378:metabolism*; D023303:Oxazolidinones; D011355:Prodrugs / Q000737:chemistry / Q000378:metabolism*; D011433:Propranolol / Q000737:chemistry*; D051381:Rats; D013053:Spectrophotometry; D013237:Stereoisomerism; D014020:Tissue Extracts / Q000378:metabolism
D002021:Buffers; D009281:Naphthalenes; D010080:Oxazoles; D023303:Oxazolidinones; D011355:Prodrugs; D014020:Tissue Extracts; C068321:3-isopropyl-5-(1-naphthoxymethyl)oxazolidine; D011433:Propranolol