Synthesis, characterization and in vitro hydrolysis of a gemfibrozil-nicotinic acid codrug for improvement of lipid profile

European Journal of Pharmaceutical Sciences

Volumn 43, Issue 3, 2011, Pages 99-108

  Qandil, Amjad M ^a   Rezigue, Meriem M ^a   Tashtoush, Bassam M ^a  

^a JORDAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Jordan)

Author keywords

Arrhenius equation; Codrug; Gemfibrozil; Hydrolysis; Hyperlipidemia; Nicotinic acid

Indexed keywords

2 [5 (2,5 DIMETHYLPHENOXY) 2,2 DIMETHYLPENTANOYLOXY]ETHYL NICOTINATE; 2 HYDROXYETHYL 5 (2,5 DIMETHYLPHENOXY) 2,2 DIMETHYLPENTANOATE; APOLIPOPROTEIN; GEMFIBROZIL; LIPOPROTEIN; NICOTINIC ACID; PHOSPHATE BUFFERED SALINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DEGRADATION; DRUG HALF LIFE; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH TEMPERATURE; HUMAN; HYDROLYSIS; INFRARED SPECTROSCOPY; LIVER HOMOGENATE; PARTITION COEFFICIENT; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; GEMFIBROZIL; HALF-LIFE; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; HYPERLIPIDEMIAS; KINETICS; LIVER; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NIACIN; NICOTINIC ACIDS; PLASMA; PRODRUGS; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE;

EID: 79956364015     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.03.012     Document Type: Article

References (49)

1. Abdel-Azeem, A.Z., Abdel-Hafez, A.A., El-Karamany, G.S., Farag, H.H., 2009. Chlorzoxazone esters of some non-steroidal anti-inflammatory (NSAI) carboxylic acids as mutual prodrugs: design, synthesis, pharmacological investigations and docking studies. Bioorganic and Medicinal Chemistry 17, 3665-3670.
2. Birjmohun, R.S., Hutten, B.A., Kastelein, J.J.P., Stroes, E.S.G., 2005. Efficacy and safety of high-density lipoprotein cholesterol-increasing compounds a meta-analysis of randomized controlled trials. Journal of the American College of Cardiology 45 (2), 185-197. (Pubitemid 40094724)
3. Carlson, L.A., 2004. Niaspan, the prolonged release preparation of nicotinic acid (niacin), the broad-spectrum lipid drug. International Journal of Clinical Practice 58 (7), 706-713.
4. Carlson, L.A., 2005. Nicotinic acid: the broad-spectrum lipid drug. A 50th Anniversary Review. Journal of Internal Medicine 258 (2), 94-114.
5. Cynkowska, G., Cynkowski, T., Al-Ghananeem, A., Guo, H., Ashtona, P., Crooks, P.A., 2005. Novel antiglaucoma prodrugs and codrugs of ethacrynic acid. Bioorganic and Medicinal Chemistry Letters 15, 3524-3527. (Pubitemid 40942047)
6. Davidson, M.H., 2008. Niacin use and cutaneous flushing: mechanisms and strategies for prevention. American Journal of Cardiology 101 (8 Suppl. 1), S14-S19.
7. Davidson, M.H., Toth, P.P., 2004. Comparative effects of lipid-lowering therapies. Progress in Cardiovascular Diseases 47 (2), 73-104. (Pubitemid 39600944)
8. Dean, B.B., Borenstein, J.E., Henning, J.M., Knight, K., Merz, C.N.B., 2004. Can change in high-density lipoprotein cholesterol levels reduce cardiovascular risk? American Heart Journal 147 (6), 966-976.
9. Dhaneshwar, S.S., Kandpal, M., Vadnerkar, G., Rathi, B., Kadam, S.S., 2007. Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrug of 5-aminosalicylic acid for colon-specific drug delivery inflammatory bowel disease. European Journal of Medicinal Chemistry 42, 885-890.
10. Ermer, J., Miller, J.H.M., 2005. Method Validation in Pharmaceutical Analysis, A Guide to Best Practice. Wiley-VCH Verlag GmbH, Heppenheim.
11. FDA (Cartographer), 2001. Guidance for Industry Bioanalytical Method Validation. Retrieved from http://www.fda.gov/downloads/Drugs/ GuidanceComplianceRegulatoryInformation/Guidances/UCM070107.pdf.
12. Ganji, S.H., Kamanna, V.S., Kashyap, M.L., 2003. Niacin and cholesterol: role in cardiovascular disease. Journal of Nutritional Biochemistry 14 (6), 298-305. (Pubitemid 36836234)
13. Gurakar, A., Hoeg, J.M., Kostner, G., Papadopoulos, N.M., Brewer Jr., H.B., 1985. Levels of lipoprotein Lp(a) decline with neomycin and niacin treatment. Atherosclerosis 57 (2-3), 293-301.
14. Hamad, M.O., Kiptoo, P.K., Stinchcomb, A.L., Crooks, P.A., 2006. Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6[beta]-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents. Bioorganic and Medicinal Chemistry 14 (20), 7051-7061. doi:10.1016/j.bmc.2006.06.018. (Pubitemid 44307636)
15. Hassan, H.B., Kata, M., Ero{combining double acute accent}s, I., Aigner, Z., 2004. Preparation and investigation of inclusion complexes containing Gemfibrozil and DIMEB. Journal of Inclusion Phenomena and Macrocyclic Chemistry 50 (3), 219-225. doi:10.1007/s10847-004-3124-7.
16. Herrera, E., Lasuncion, M.A., Castro, M., Gomez Coronado, D., Martin, A., Quack, G., 1988. Studies with etofibrate in the rat. Part I: effects on glycerol, free fatty acid and triacylglycerol metabolism. Biochimica et Biophysica Acta 963 (1), 42-52.
17. International Conference on Harmonisation, 1997. Guidance for Industry, Q2B Validation of Analytical Procedures: Methodology from http://www.fda.gov/ downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/ucm073384.pdf.
18. International Conference on Harmonisation, 2005. Validation of Analytical Procedures: Text and Methodology Q2(R1), from http://www.ich.org/LOB/media/ MEDIA417.pdf.
19. IPCS Inchem, 1995. Nicotinic acid (CAS No: 59-67-6). Retrieved from http://www.inchem.org/documents/sids/sids/59676.pdf.
20. Karnes, H.T., March, C., 1993. Precision, accuracy, and data acceptance criteria in biopharmaceutical analysis. Pharmaceutical Research 10 (10), 1420-1426. (Pubitemid 23302656)
21. Kashyap, M.L., 1984. The effect of gemfibrozil on plasma lipids and lipoproteins in man. Vascular Medicine 2, 16-21. (Pubitemid 15135568)
22. Kiptoo, P.K., Hamad, M.O., Crooks, P.A., Stinchcomb, A.L., 2006. Enhancement of transdermal delivery of 6-β- naltrexolviaacodruglinkedtohydroxybupropion. Journal of Controlled Release 113, 137-145.
23. Kiptoo, P.K., Paudel, K.S., Hammell, D.C., Hamad, M.O., Crooks, P.A., Stinchcomb, A.L., 2008. In vivo evaluation of a transdermal codrug of 6-β-naltrexol linked to hydroxybupropion in hairless guinea pigs. European Journal of Pharmaceutical Sciences 33, 371-379.
24. Lindholm, J., 2004. Development and Validation of HPLC Methods for Analytical and Preparative Purposes: Acta Universitatis Upsaliensis. Ph.D., University of Uppsala, Uppsala.
25. Link, J.J., Rohatgi, A., de Lemos, J.A., 2007. HDL cholesterol: physiology, pathophysiology, and management. Current Problems in Cardiology 32 (5), 268-314. (Pubitemid 46669678)
26. Luner, P.E., Babu, S.R., Radebaugh, G.W., 1994. The effects of bile salts and lipids on the physicochemical behavior of gemfibrozil. Pharmaceutical Research 11 (12), 1755-1760. doi:10.1023/a:1018967401000. (Pubitemid 24377087)
27. Manninen, V., Elo, M., Frick, M., et al., 1998. Lipid alterations and decline in the incidence of coronary heart disease in the Helsinki Heart Study. JAMA 260, 641-651.
28. Manninen, V., Malkonen, M., Eisalo, A., Virtamo, J., Tuomilehto, J., Kuusisto, P., 1982. Gemfibrozil in the treatment of dyslipidaemia. A 5-year follow-up study. Acta Medica Scandinavica 668 (Suppl.), 82-87.
29. Martindale: The Complete Drug Reference, 2010a. Clofibrate Retrieved March 7th, 2011, from http://www.medicinescomplete.com/mc/martindale/current/ms- 1341-x.htm?q=clofibrate&t=search&ss=text&p=1--hit.
30. Martindale: The Complete Drug Reference, 2010b. Etofibrate Retrieved March 7th, 2011, from http://www.medicinescomplete.com/mc/martindale/2009/12719- c.htm.
31. Martindale: The Complete Drug Reference, 2010c. Gemfibrozil Retrieved March 7th, 2011, from http://www.medicinescomplete.com/mc/martindale/current/ 1349-v.htm?q=gemfibrozil&t=search&ss=text&p=1--hit.
32. Meyers, C.D., Liu, P., Kamanna, V.S., Kashyap, M.L., 2007. Nicotinic acid induces secretion of prostaglandin D2 in human macrophages: an in vitro model of the niacin flush. Atherosclerosis 192 (2), 253-258. (Pubitemid 46726325)
33. Ramires, J., Mansur, A., Solimene, M., Maranhão, R., Chamone, D., da Luz, P., Pileggi, F., 1995. Effect of gemfibrozil versus lovastatin on increased serum lipoprotein(a) levels of patients with hypercholesterolemia. International Journal of Cardiology 48 (2), 115-120.
34. Rautio, J., Kumpulainen, H., Heimbach, T., Oliyai, R., Oh, D., Järvinen, T., Savolainen, J., 2008. Prodrugs: design and clinical applications. Nature Reviews Drug Discovery 7, 255-270. (Pubitemid 351324639)
35. Raza, J.A., Babb, J.D., Movahed, A., 2004. Optimal management of hyperlipidemia inprimary prevention of cardiovascular disease. International Journal of Cardiology 97 (3), 355-366. (Pubitemid 39550681)
36. Samson, R.H., 2002. Pharmaceutical initiatives to combat atherosclerosis - what to do with the good, the bad, and the ugly lipoproteins. Seminars in Vascular Surgery 15 (4), 204-215. (Pubitemid 36009029)
37. Shabir, G.A., 2003. Validation of high-performance liquid chromatography methods for pharmaceutical analysis: understanding the differences and similarities between validation requirements of the US Food and Drug Administration. The US Pharmacopeia and the International Conference on Harmonization Journal of Chromatography A 987 (1-2), 57-66. (Pubitemid 36140080)
38. Simões, M.F., Valente, E., Rodríguez Gómez, M.J., Anes, E., Constantino, L., 2009. Lipophilic pyrazinoic acid amide and ester prodrugs stability, activation and activity against M. tuberculosis. European Journal of Pharmaceutical Sciences 37, 257-263.
39. Sposito, A.C., Mansur, A.P., Maranhão, R.C., Rodrigues-Sobrinho, C.R.M., Coelho, O.R., Ramires, J.A.F., 2001. Etofibrate but not controlled-release niacin decreases LDL cholesterol and lipoprotein (a) in type IIb dyslipidemic subjects. Brazilian Journal of Medical and Biological Research 34 (2), 177-182.
40. Steiner, G., 2005. Fibrates and coronary risk reduction. Atherosclerosis 182 (2), 199-207. (Pubitemid 41267187)
41. Superko, H.R., Garrett, B.C., King III, S.B., Momary, K.M., Chronos, N.A., Wood, P.D., 2009. Effect of combination nicotinic acid and gemfibrozil treatment on intermediate density lipoprotein, and subclasses of low density lipoprotein and high density lipoprotein in patients with combined hyperlipidemia. American Journal of Cardiology 103 (3), 387-392.
42. Superko, R., Garrett, B., King III, S., Superko, S., 2006. Nicotinic acid and gemfibrozil combination for the treatment of familial combined hyperlipidemia and the effect on LDL and HDL subclass distribution. Atherosclerosis Supplements 7 (3), 476.
43. Taher, T.H., Dzavik, V., Reteff, E.M., Pearson, G.J., Woloschuk, B.L., Francis, G.A., 2002. Tolerability of statin-fibrate and statin-niacin combination therapy in dyslipidemic patients at high risk for cardiovascular events. American Journal of Cardiology 89 (4), 390-394.
44. Taylor, A.J., Stanek, E.J., 2008. Flushing and the HDL-C response to extended-release niacin. Journal of Clinical Lipidology 2 (4), 285-288.
45. Thomas, B., Burgess, J., Coleman, D., Scheffler, N., Jeffcoat, A.R., Dix, K., 1999. Isolation and identification of novel metabolites of gemfibrozil in rat urine. Drug Metabolism and Disposition 27 (1), 147-157. (Pubitemid 29061015)
46. Todd, P.A., Ward, A., 1988. Gemfibrozil. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in dyslipidaemia. Drugs 36 (3), 314-339.
47. Yalkowsky, S.H., Morozowich, W., 1980. The physical chemical basis for the design of orally active prodrugs. In: Aridns, E.J. (Ed.), Drug Design (vol. IX). Academic Press, New York.
48. Zema, M.J., 2010. Gemfibrozil, nicotinic acid and combination therapy in patients with isolated hypoalphalipoproteinemia: a randomized, open label, crossover study. Journal of the American College of Cardiology 35 (3), 640-646.
49. Zovko, M., Barbaric, M., Zorc, B., Hafner, A., Filipovic-Grcic, J., 2005. Synthesis of fenoprofen and gemfibrozil styrene-maleic acid copolymer conjugates. Acta Pharmaceutica 55, 169-176. (Pubitemid 40992428)