Literature DB >> 28845100

Determination of the enantiomeric purity of epinephrine by HPLC with circular dichroism detection.

Douglas Kirkpatrick1, Jingyue Yang1, Michael Trehy1.   

Abstract

Several hundred drug substances approved by the U.S. Food and Drug Administration are chiral molecules. For the enantiomeric purity assessment, current practice is to develop separation techniques using chiral columns or mobile phase modifiers to separate enantiomers before detection. An alternative approach is to use currently accepted HPLC assay methods and use chiral-specific detectors to confirm whether the correct enantiomer is present. In this paper, adding a circular dichroism (CD) detector to an achiral HPLC method from the US Pharmacopeia (USP) is shown to be amenable for the determination of the enantiomeric purity of epinephrine, a substance used to treat anaphylaxis. This HPLC-UV-CD approach was able to detect the inactive D-(+) enantiomer at 1% of the total epinephrine composition. The linearity, accuracy, and precision of HPLC-UV-CD were evaluated and compared to analyses using a chiral HPLC method. Additionally, an epinephrine drug product was analyzed for assay (concentration) and enantiomeric purity. The results from achiral and chiral methods were identical within the experimental error. Overall, achiral chromatography performed using a USP method with CD detection may serve as a general means of determining chiral drug enantiomer purity and avoids the need for the development of additional chiral-specific methods for each individual drug.

Entities:  

Keywords:  Adrenaline; HPLC; chiral; circular dichroism; enantiomer; epinephrine

Year:  2017        PMID: 28845100      PMCID: PMC5568804          DOI: 10.1080/10826076.2017.1333962

Source DB:  PubMed          Journal:  J Liq Chromatogr Relat Technol        ISSN: 1082-6076            Impact factor:   1.312


  25 in total

1.  Reliable assay of extreme enantiomeric purity values by a new circular dichroism based HPLC detection system.

Authors:  C Bertucci; V Andrisano; V Cavrini; E Castiglioni
Journal:  Chirality       Date:  2000-02       Impact factor: 2.437

2.  Determination of optical purity by nonenantioselective LC using CD detection.

Authors:  E Bossu'; V Cotichini; G Gostoli; A Farina
Journal:  J Pharm Biomed Anal       Date:  2001-12       Impact factor: 3.935

3.  Achiral liquid chromatography with circular dichroism detection for the determination of carnitine enantiomers in dietary supplements and pharmaceutical formulations.

Authors:  Fernando de Andrés; Gregorio Castañeda; Angel Ríos
Journal:  J Pharm Biomed Anal       Date:  2009-02-27       Impact factor: 3.935

4.  Supercritical fluid extraction--achiral liquid chromatography with circular dichroism detection for the determination of menthone enantiomers in natural peppermint oil samples.

Authors:  Mohammed Zougagh; Purificación Aranda; Gregorio Castañeda; Angel Ríos
Journal:  Talanta       Date:  2009-03-31       Impact factor: 6.057

5.  Chiral analysis of milnacipran by a nonchiral HPLC--circular dichroism: improvement of the linearity of dichroic response by temperature control.

Authors:  Marie Lecoeur-Lorin; Raphaël Delépée; Jean-Paul Ribet; Philippe Morin
Journal:  J Sep Sci       Date:  2008-09       Impact factor: 3.645

6.  Outdated EpiPen and EpiPen Jr autoinjectors: past their prime?

Authors:  F E Simons; X Gu; K J Simons
Journal:  J Allergy Clin Immunol       Date:  2000-05       Impact factor: 10.793

7.  Stereoselective modification of circular dichroism spectra of rat lung beta-adrenoceptor protein preparation by enantiomers of epinephrine.

Authors:  P N Patil; P Eraundorfer; P K Dutta
Journal:  Chirality       Date:  1996       Impact factor: 2.437

Review 8.  Anaphylaxis and emergency treatment.

Authors:  Hugh A Sampson
Journal:  Pediatrics       Date:  2003-06       Impact factor: 7.124

9.  Analysis of USP epinephrine injections for potency, impurities, degradation products, and d-enantiomer by liquid chromatography, using ultraviolet and electrochemical detectors.

Authors:  R D Kirchhoefer; G M Sullivan; J F Allgire
Journal:  J Assoc Off Anal Chem       Date:  1985 Mar-Apr

10.  Applied circular dichroism: a facile spectroscopic tool for configurational assignment and determination of enantiopurity.

Authors:  Macduff O Okuom; Raychelle Burks; Crysta Naylor; Andrea E Holmes
Journal:  J Anal Methods Chem       Date:  2015-01-29       Impact factor: 2.193

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  1 in total

1.  Enantiomeric impurity analysis using circular dichroism spectroscopy with United States Pharmacopeia liquid chromatographic methods.

Authors:  Douglas Kirkpatrick; Margaret Fain; Jingyue Yang; Michael Trehy
Journal:  J Pharm Biomed Anal       Date:  2018-04-24       Impact factor: 3.935

  1 in total

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