title: Resolution of the enantiomers of ibuprofen; comparison study of diastereomeric method and chiral stationary phase method.
abstract: In this study, an indirect diastereomeric method and a direct method utilizing a chiral stationary phase (CSP) were investigated for the resolution of ibuprofen enantiomers. In the indirect method, ethylchloroformate (ECF) and 2-ethoxy-1-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) were utilized as first-step derivatizing reagents in acetonitrile or toluene. In the direct CSP method, ibuprofen enantiomers were derivatized to p-nitrobenzyl ureides and then resolved on an (R)-(-)-(1-naphthyl)ethylurea CSP column. The derivatization procedure took place in 10 min with an overall inversion efficiency of 90.3%. Racemization was not observed under the derivatization conditions used. The HPLC-CSP method was utilized to study the pharmacokinetics of ibuprofen enantiomers in dog plasma after a single oral administration of 200 mg of ibuprofen racemate.
authors.affiliation: Biopharmaceutic Research Branch, Food and Drug Administration, Washington, DC 20204.
authors.forename: H Y
authors.initials: HY
authors.lastname: Ahn
authors.forename: G K
authors.initials: GK
authors.lastname: Shiu
authors.forename: W F
authors.initials: WF
authors.lastname: Trafton
authors.forename: T D
authors.initials: TD
authors.lastname: Doyle
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004285:Dogs; D005563:Formic Acid Esters; D007052:Ibuprofen / Q000737:chemistry / Q000302:isolation & purification* / Q000493:pharmacokinetics; D007202:Indicators and Reagents; D011804:Quinolines; D013237:Stereoisomerism
chemical_list: D005563:Formic Acid Esters; D007202:Indicators and Reagents; D011804:Quinolines; C007658:ethyl chloroformate; C000470:EEDQ; D007052:Ibuprofen