Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol

The chiral separation of enantiomers is crucial for pharmacovigilance within drug discovery. Although a large number of prescribed medications are marketed as pure enantiomers, this is not always the case and many are in fact racemic mixtures. Drug scandals, such as that of Thalidomide in 1961, prov...

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Main Authors: Guerrero M.M. López, Díaz A. Navas, Sánchez F. García, Corrall H.
Format: Article
Language:English
Published: De Gruyter 2019-06-01
Series:Open Chemistry
Subjects:
Online Access:https://doi.org/10.1515/chem-2019-0049
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author Guerrero M.M. López
Díaz A. Navas
Sánchez F. García
Corrall H.
author_facet Guerrero M.M. López
Díaz A. Navas
Sánchez F. García
Corrall H.
author_sort Guerrero M.M. López
collection DOAJ
description The chiral separation of enantiomers is crucial for pharmacovigilance within drug discovery. Although a large number of prescribed medications are marketed as pure enantiomers, this is not always the case and many are in fact racemic mixtures. Drug scandals, such as that of Thalidomide in 1961, provide a clear example of the social and economic repercussions that can be caused by negligence of these chiral compounds. Two high performance liquid chromatography (HPLC) methods are presented to determine, separate and quantitate a commonly prescribed chiral beta blocker, (-)-Alprenolol. The first method utilises a chiral column to physically separate the two enantiomers of Alprenolol in 25 minutes, before quantitating with two detectors. Fluorimetry gave the better limit of detection of 0.16-0.41ng and a correlation coefficient of 0.999. The second method used an achiral column coupled with polarimetry to quantitate (-)-Alprenolol without the need for physical separation in 10 minutes. The limit of detection achieved was 27-37μg and demonstrated a correlation coefficient of -0.999.
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spelling doaj.art-4dc7ad13b3c84290beafacacc5cdc1022022-12-21T18:33:44ZengDe GruyterOpen Chemistry2391-54202019-06-0117142943710.1515/chem-2019-0049chem-2019-0049Chiral and Achiral Enantiomeric Separation of (±)-AlprenololGuerrero M.M. López0Díaz A. Navas1Sánchez F. García2Corrall H.3Faculty of Sciences, University of Málaga, Av. Cervantes, 2, 29071Málaga, SpainFaculty of Sciences, University of Málaga, Av. Cervantes, 2, 29071Málaga, SpainFaculty of Sciences, University of Málaga, Av. Cervantes, 2, 29071Málaga, SpainFaculty of Sciences, University of Málaga, Av. Cervantes, 2, 29071Málaga, SpainThe chiral separation of enantiomers is crucial for pharmacovigilance within drug discovery. Although a large number of prescribed medications are marketed as pure enantiomers, this is not always the case and many are in fact racemic mixtures. Drug scandals, such as that of Thalidomide in 1961, provide a clear example of the social and economic repercussions that can be caused by negligence of these chiral compounds. Two high performance liquid chromatography (HPLC) methods are presented to determine, separate and quantitate a commonly prescribed chiral beta blocker, (-)-Alprenolol. The first method utilises a chiral column to physically separate the two enantiomers of Alprenolol in 25 minutes, before quantitating with two detectors. Fluorimetry gave the better limit of detection of 0.16-0.41ng and a correlation coefficient of 0.999. The second method used an achiral column coupled with polarimetry to quantitate (-)-Alprenolol without the need for physical separation in 10 minutes. The limit of detection achieved was 27-37μg and demonstrated a correlation coefficient of -0.999.https://doi.org/10.1515/chem-2019-0049separationenantiomerchiralachiralhplc
spellingShingle Guerrero M.M. López
Díaz A. Navas
Sánchez F. García
Corrall H.
Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
Open Chemistry
separation
enantiomer
chiral
achiral
hplc
title Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
title_full Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
title_fullStr Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
title_full_unstemmed Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
title_short Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
title_sort chiral and achiral enantiomeric separation of alprenolol
topic separation
enantiomer
chiral
achiral
hplc
url https://doi.org/10.1515/chem-2019-0049
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AT diazanavas chiralandachiralenantiomericseparationofalprenolol
AT sanchezfgarcia chiralandachiralenantiomericseparationofalprenolol
AT corrallh chiralandachiralenantiomericseparationofalprenolol