Cover Image

The study of separation of delapril’s s-cis/s-trans isomers and development and validation of an analytical method for the estimation of delapril by reversed-phase liquid chromatography

Afef Ben Amar, Mbarek Abidi, Najib Ben Hamida

Abstract


Delapril is an angiotensin converting enzyme (ACE) inhibitor, which exists as a mixture of rotational s-trans and s-cis isomers due to the rotation of the amide bond. Although these stereoisomers do interconvert by rotation about the amide bond, the rate of interconversion is slow, allowing separation of the isomers on the chromatographic time scale. The effect of the flow-rate, column temperature, pH, organic modifier, and counter-ion on the peak shape and the separation of the s-cis and s-trans conformers of delapril was investigated by HPLC. It was proved that the separation selectivity was improved by either a decrease of the flow-rate or an increase of the amount of the organic modifier or the addition of a positively charged counter ion. Delapril was then estimated by a reversed-phase liquid chromatographic method. This method was subsequently validated for specificity, linearity, accuracy and precision, according to the International Conference on Harmonization (ICH) guidelines. An NMR study indicates that the molecule exists as a mixture of rotational cis and trans isomers which confirms the results obtained by HPLC. The isomer ratio integrated from the obtained 1H NMR result was 75:25 in DMSO-d6 at 298 K, where the s-trans isomer was the major form.

Full Text:

PDF

References


- E. Redenti, M. Zanol, G. Amari, P. Ventura, G. Fronza, A. Bacchi and G. Pelizzi, Il Farmaco, 1998, 53, 214-223.

- R. Razzetti and D. Acerbi, American Journal of Cardiology, 1995, 75, 7F-12F.

- V. Todeschini, M. S. Sangoi and N. M. Volpato, European Journal of Mass Spectrometry, 2011, 17, 3, 287-296.

- V. Todeschini, A. S. Meira, M. S. Sangoi, A. B. Barth, C. S. Paim and N. M. Volpato, Journal of Liquid Chromatography and Related Technologies, 2012, 35, 5, 603-620.

– V. Todeschini, A. T. Barden, L. L. Sfair, M. S. Sangoi and N. M. Volpato, ActaChimicaSlovenica, 2013, 60, 2, 335–342.

– V. Todeschini and M. S. Sangoi,Journal of AOAC International, 2014, 97, 1, 114-120.

– V. Todeschini, P. R. de Oliveira, L. S. Bernardi, R. L. Pereira, C. E. M. de Campos, M. A. S. Silva and N. M. Volpato, Journal of Thermal Analysis and Calorimetry, 2014, 115, 2295–2301.

- P. J. Rudzki, K. Buś, H. Ksycińska,and K. Kobylińska, Journal of Pharmaceutical and Biomedical Analysis, 2007, 44, 356–367.

- O. Trapp, G. Schoetz,and V. Schurig, Chirality, 2001, 13, 403-417.

-A. Ben Amar, M. Abidi,and N. Ben Hamida, Journal de la Société Chimique de Tunisie, 2013, 15,9-17.

-D. Perrett and P. L. Drury, Journal of Liquid Chromatography, 1982, 5, 97-110.

- T. Kato, AnalyticaChimicaActa, 1985, 175, 339-344.

- S. Gustafsson, B.M. Eriksson, and I. Nilsson, Journal of Chromatography, 1990, 506, 75–83.

- J. Salamoun and K. Slais, Journal of Chromatography, 1991, 537, 249–264.

- R. Bhushan and D. Gupta, Journal of Chromatography B, 2006, 837, 133–137.

- T. Nishikawa, Y. Hayashi, S. Suzuki, H. Kubo, and H. Ohtani, Analytical Sciences, 1996, 12, 561-564.

-A.S. Rathore, and C. Horváth, Journal of Chromatography A, 1997, 787, 1-12.

- R. Ledger and E. Stellwagen, Journal of Pharmacy and Pharmacology, 2005, 57, 845–850.

- R. Cirilli, C. Di Bugno, and F. La Torre, Chromatographia, 1999, 49, 628-634.

- H. Trabelsi, S. Bouabdallah, S. Sabbah, F. Raoufi, and K. Bouzouita, Journal of Chromatography, 2000, 871, 189-199.

- S. Bouabdallah, H. Trabelsi, K. Bouzouita, and S. Sabbah, Journal of Biochemical and Biophysical Methods, 2002, 54, 391–405.

- S. Bouabdallah, H. Trabelsi, T. Ben Dhia, S. Sabbah, K. Bouzouita,and R. Khaddar, Journal of Pharmaceutical and Biomedical Analysis, 2003, 31, 731-741.

- S. Bouabdallah, H. Trabelsi, M. T. Ben Dhia, and N. Ben Hamida, Chromatographia, 2012, 75, 1247-1255.

- S. Bouabdallah, M. T. Ben Dhia,and M. R. Driss, International Journal of Analytical Chemistry, 2014, 1-8.

- S. Gebauer, S. Friebe, G. Scherer, G. Gübitz, and G-J. Krauss, Journal of Chromatographic Science, 1998, 36, 388-394.

- S. Gikas, F. Tsopelas, C. Giaginis, J. Dimitrakopoulos, T. Livadara, H. Archontaki, and A. Tsantili-Kakoulidou, Journal of Pharmaceutical and Biomedical Analysis, 2008, 48, 739–743.

- N. Tanaka, H. Goodell, and B.L. Karger, Journal of Chromatography, 1978, 158, 233–248.

- X-Z. Qin, J. DeMarco,and D. P. Ip, Journal of Chromatography, 1995, 707, 245–254.

- A. Kálmán, F. Thunecke, R. Schmidt, P.W. Schiller, and C. Horváth, 1996, 729, 155–171.

-medicine.cug.net/drug/05/05_03_02.htm.

- United States Pharmacopeia, 29th Edition. United States Pharmacopeial Convention, Inc, Twinbrook Parkway, Rockville, MD, USA.pp. 1623, 2675-2693, 3050-3053, 3392-3394, 2006.

- US Food and Drug Administration, Center for Drug Evaluation and Research, Guidance for Industry: Analytical Procedures and Methods Validation. Chemistry, Manufacturing, and Controls Documentation DRAFT GUIDANCE, Rockville, MD, 2000.

http://www.fda.gov/CDER/GUIDANCE/2396dft.pdf.

- International Conference on Harmonization (ICH) of Technical Requirements for the registration of Pharmaceuticals for Human Use, Guideline for Industry Q2A. Text on Validation of Analytical Procedures, Geneva: 1995.

http://www.fda.gov/cder/Guidance/ichq2a.pdf.




DOI: http://dx.doi.org/10.13171/mjc.3.4.2014.15.08.16

Refbacks

  • There are currently no refbacks.


Copyright (c) 2015 Mediterranean Journal of Chemistry