Isolation of a major metabolite (i-OHAP) of aprindine and its identification as N-[3-(N,N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol.
i-OHAP, a major metabolite of aprindine (AP), was isolated by TLC from rat feces and identified as N-13-(N,N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol, based on 1H-NMR, the H-H correlation spectroscopy (COSY) spectrum, MS and LC-MS. Its structure was also confirmed by comparison with the synthesized compound. The hydroxy group of i-OHAP was located at the 5-position of the indan ring. AP is a prochiral compound, and the metabolism of AP to i-OHAP was stereoselective. The ratio of (+)/(-)-i-OHAP in rat feces and in human urine was about 5 and 15, respectively.
Shimizu
M
M
Department of Biopharmaceutics, Meiji College of Pharmacy, Tanashi, Tokyo, Japan.
Takatori
K
K
Kajiwara
M
M
Ogata
H
H
D000328:Adult; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000493:pharmacokinetics*; D001073:Aprindine / Q000031:analogs & derivatives* / Q000378:metabolism / Q000493:pharmacokinetics* / Q000652:urine; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005243:Feces / Q000737:chemistry; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism
D000889:Anti-Arrhythmia Agents; C113787:N-(3-(N,N-diethylamino)propyl)-N-phenyl-2-aminoindan-5-ol; D001073:Aprindine