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Direct high‐performance liquid chromatographic separation of penbutolol enantiomers on a cellulose tris‐3,5‐dimethylphenyl carbamate chiral stationary phase
Author(s) -
AboulEnein Hassan Y.,
Islam M. Rafiqul
Publication year - 1989
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530010409
Subject(s) - chemistry , enantiomer , chromatography , carbamate , silica gel , tris , high performance liquid chromatography , elution , resolution (logic) , chiral column chromatography , cellulose , phase (matter) , chiral stationary phase , organic chemistry , biochemistry , artificial intelligence , computer science
Penbutolol is a β‐adrenoceptor blocking agent, and it contains the clinically relevant (−)‐S‐enantiomer. It was reported that the (+)‐R‐enantiomer of penbutolol is pharmacologically 50 times less active than the (−)‐S‐isomer in β‐sympatholysis and without intrinsic sympathomimetic activity and refractory period in the heart muscle. Furthermore, the (+)‐R‐enantiomer does possess mutagenic activity. A high‐performance liquid chromatographic (HPLC) method is described for direct identification, stereochemical separation, and quantitation of (+)‐R‐enantiomer in the clinically used (−)‐S‐isomer. The method involves the use of cellulose tris‐3,5‐dimethylphenyl carbamate chiral stationary phase coated on silica gel (OD‐Chiralcel column). The capacity factors ( k ′) for the first eluted enantiomer and stereochemical separation factor (α) obtained were 1.32 and 1.98, respectively. The maximum stereochemical resolution factor ( R ) was 5.05. The method could be applied for optical purity determination of (−)‐(S)‐penbutolol in pharmaceutical formulation to detect for the presence of the undesirable (+)‐R‐enantiomer.