Metabolites of chloroquine: some observations on desethylchloroquine and N-acetyldesethylchloroquine.
The major metabolite of chloroquine, (+)-desethylchloroquine, produced by stereoselective N-dealkylation of the drug, was obtained in 81.5% enantiomeric purity by resolution of racemic desethylchloroquine using an atropisomeric resolving agent and was shown by circular dichroism to have the absolute (S)-configuration. The minor metabolite N-acetyldesethylchloroquine was prepared in both the racemic and the (S)-(+)-form.
Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco 94143-0446.
A M
AM
Ansari
J C
JC
Craig
D000107:Acetylation; D002738:Chloroquine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D002855:Chromatography, Thin Layer; D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared / Q000379:methods; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013237:Stereoisomerism
C090234:N-acetyldesethylchloroquine; D002738:Chloroquine; C007278:desethylchloroquine