Pharmaceutical salts: A formulation trick or a clinical conundrum?

British Journal of Cardiology

Volumn 16, Issue 6, 2009, Pages 281-286

  Patel, Aateka ^a   Jones, Stuart A ^a   Ferro, Albert ^a   Patel, Nilesh ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Bioequivalence; Clopidogrel; Perindopril; Pharmaceutical salt; Pharmacokinetics

Indexed keywords

ACETYLSALICYLIC ACID; ALPRENOLOL; AMLODIPINE; AMLODIPINE ADIPATE; AMLODIPINE BESYLATE; AMLODIPINE CAMYSLATE; AMLODIPINE MALEATE; CHLORIDE; CLOPIDOGREL; DEXTROPROPOXYPHENE; DEXTROPROPOXYPHENE NAPSILATE; DIETHYLAMINE; DRUG ADDITIVE; ETHYLAMINE; ETHYLENEDIAMINE; FLUTICASONE PROPIONATE; GENERIC DRUG; IBUPROFEN; LANSOPRAZOLE; NITRATE; PERINDOPRIL; PERINDOPRIL TERT BUTYLAMINE; PHARMACEUTICAL SALT; PRASUGREL; PROPIONIC ACID DERIVATIVE; SALBUTAMOL SULFATE; SODIUM; SULFATE; TRIETHYLAMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACUTE HEART INFARCTION; AREA UNDER THE CURVE; ARTERY THROMBOSIS; BIOEQUIVALENCE; COVALENT BOND; DIGESTIVE SYSTEM ULCER; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DEVELOPMENT; DRUG EFFICACY; DRUG EXCRETION; DRUG FORMULATION; DRUG HALF LIFE; DRUG MANUFACTURE; DRUG METABOLISM; DRUG PACKAGING; DRUG QUALITY; DRUG SAFETY; DRUG STABILITY; DRUG TOLERABILITY; GASTROINTESTINAL IRRITATION; HUMAN; HYPERTENSION; IONIZATION; MAXIMUM PLASMA CONCENTRATION; MEDICAL PRACTICE; NONHUMAN; PHARMACODYNAMICS; REVIEW; THROMBOCYTE AGGREGATION; TIME TO MAXIMUM PLASMA CONCENTRATION;

EID: 77953716351     PISSN: 09696113     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (31)

1. Serajuddin ATM. Salt formation to improve drug solubility. Advanced Drug Delivery Reviews 2007;59:603-16. (Pubitemid 47285406)
2. Derendorf H, Meltzer EO. Molecular and clinical pharmacology of intranasal corticosteroids: Clinical and therapeutic implications. Allergy: European Journal of Allergy and Clinical Immunology 2008;63:1292-300.
3. Johnson M. Development of fluticasone propionate and comparison with other inhaled corticosteroids. J Allergy Clin Immunol 1998;101(4 Pt 2):S434-S439.
4. Crim C, Pierre LN, Daley-Yates PT. A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate. Clin Ther 2001;23:1339-54. (Pubitemid 32912787)
5. Berge SM, Bighley LD, Monkhouse DC. Pharmaceutical salts. J Pharm Sci 1977;66:1-19.
6. Stahl and Wermuth. Handbook of pharmaceutical salts: properties, selection, and use. Weinheim: Wiley-VCH, 2002.
7. Food and Drug Administration. Chapter 1 - Food and Drug Administration, Department of Health and Human Services. Part 320 - Bioavailability and bioequivalence requirements. Available from: http://www.access.gpo.gov/nara/cfr/ waisidx-00/21cfr320-00.html [accessed 20 June 2009].
8. European Medicines Authority. Guideline on the investigation of bioequivalence (CPMP/EWP/QWP/1401/98 Rev. 1). Available from: http://www.emea.europa.eu/pdfs/human/qwp/140198enrev1.pdf [accessed 20 June 2009].
9. Meredith P. Bioequivalence and other unresolved issues in generic drug substitution. Clin Ther 2003;25:2875-90. (Pubitemid 37510596)
10. Verbeek RK, Kanfer I, Walker RB. Generic substitution: the use of medicinal products containing different salts and implications for safety and efficacy. Eur J Pharm Sci 2006;28:1-6.
11. Gould PL. Salt selection for basic drugs. Int J Pharm 1986;33:201-17. (Pubitemid 17197805)
12. Leo A, Hansch C, Elkins D. Partition coefficients and their uses. Chem Rev 1971;71:525-616.
13. Sarveiya V, Templeton JF, Benson HAE. Ion-pairs of ibuprofen: increased membrane diffusion. J Pharm Pharmacol 2004;56:717-24. (Pubitemid 38801687)
14. Davies G. Changing the salt, changing the drug. Pharm J 2001;266:322-3. (Pubitemid 32222070)
15. Telejko E. Perindopril arginine: benefits of a new salt of the ACE inhibitor perindopril. Curr Med Res Opin 2007;23:953-60. (Pubitemid 46799577)
16. Olovson S-G, Havu N, Regardh C-G et al. Oesophageal ulcerations and plasma levels of different alprenolol salts: potential implications for the clinic. Acta Pharmacol Toxicol 1986;58:55-60. (Pubitemid 16212800)
17. Kim SH, Kim YD, Lim DS et al. Results of a phase III, 8-week, multicenter, prospective, randomized, double-blind, parallel-group clinical trial to assess the effects of amlodipine camsylate versus amlodipine besylate in Korean adults with mild to moderate hypertension. Clin Ther 2007;29:1924-36.
18. Lee H-Y, Kang H-Y, Koo B-K et al. Clinic blood pressure responses to two amlodipine salt formulations, adipate and besylate, in adult Korean patientswith mild to moderate hypertension: a multicentre, randomized, double-blind, parallel-group, 8-week comparison. Clin Ther 2005;27:728-39. (Pubitemid 41583520)
19. Food and Drug Administration. Amlodipine citizen petition. Available from: http://www.fda.gov/ohrms/dockets/dailys/03/Sept03/090303/03p-0408-cp00001- 08-Tab-G-vol3.pdf [accessed 20 June 2009].
20. Center for Drug Evaluation and Research (CDER). Division of cardiovascular and renal products. Revised secondary CDTI review (2009). Prasugrel hydrochloride. Available from: http://cardiobrief.files.wordpress. com/2009/02/original-fda-prasugrelreview-document.pdf [accessed 20 June 2009].
21. Clarke TA, Waskell LA. The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastatin. Drug Metab Dispos 2003;31:53-9. (Pubitemid 36735258)
22. Angiolillo DJ, Fernandez-Ortiz A, Bernardo E et al. Contribution of gene sequence variations of the hepatic cytochrome P450 3A4 enzyme to variability in individual responsiveness to clopidogrel. Arterioscler Thromb Vasc Biol 2006;26:1895-900. (Pubitemid 44305347)
23. Brandt JT, Close SL, Iturria SJ et al. Common polymorphisms of CYP2C19 and CYP2C9 affect the pharmacokinetic and pharmacodynamic response to clopidogrel but not prasugrel. J Thromb Haemost 2007;5:2429-36. (Pubitemid 350154353)
24. Giusti B, Gori AM, Marcucci R et al. Cytochrome P450 2C19 loss-of-function polymorphism, but not CYP3A4 IVS10 + 12G/A and P2Y12 T744C polymorphisms, is associated with response variability to dual antiplatelet treatment in high-risk vascular patients. Pharmacogenet Genomics2007;17:1057-64. (Pubitemid 351339490)
25. Trenk D, Hochholzer W, Fromm MF et al. Cytochrome P450 2C19 681G>A polymorphism and high on-clopidogrel platelet reactivity associated with adverse 1-year clinical outcome of elective percutaneous coronary intervention with drug-eluting or bare-metal stents. J Am Coll Cardiol 2008;51:1925-34. (Pubitemid 351636443)
26. Kim S, Lee H, Kwan E et al. Relative bioavailability, pharmacokinetics and pharmacodynamics of a new clopidogrel formulation in healthy male volunteers. Clin Pharmacol Therap 2008;83(suppl 1):S59.
27. Ki M-H, Choi M-H, Ahn K-B et al. The efficacy and safety of clopidogrel resinate as a novel polymeric salt form of clopidogrel. Arch Pharm Res 2008;31:250-8.
28. Taubert D, Kastrati A, Harlfinger S et al. Pharmacokinetics of clopidogrel after administration of a high loading dose. Thromb Haemost 2004;92:311-16. (Pubitemid 39172312)
29. European Medicines Agency. Committee for medicinal products for human use June 2009 plenary meeting monthly report. Available from: http://www.emea. europa.eu/pdfs/human/press/pr/38932609en.pdf [accessed 15 July 2009].
30. Gilard M, Arnaud B, Cornily J-C et al. Influence of omeprazole on the antiplatelet action of clopidogrel associated with aspirin: the randomized, double-blind OCLA (Omeprazole Clopidogrel Aspirin) study. J Am Coll Cardiol 2006;51:256-60.
31. Small DS, Farid NA, Payne CD et al. Effects of the proton pump inhibitor lansoprazole on the pharmacokinetics and pharmacodynamics of prasugrel and clopidogrel. J Clin Pharmacol 2008;28:475-84. (Pubitemid 351389118)