Fluoroquinolone salts with carboxylic acids

Journal of Pharmaceutical Sciences

Volumn 100, Issue 8, 2011, Pages 3160-3176

  Reddy, J Satyanarayana ^a   Ganesh, Saraswatula Viswanadha ^a   Nagalapalli, Ravikumar ^a   Dandela, Rambabu ^a   Solomon, K Anand ^a   Kumar, K Anil ^a   Goud, N Rajesh ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Carboxylic acid; Ciprofloxacin; Dissolution; Fluoroquinolone; Hydrate; Norfloxacin; Salt; Solubility; Stability; Thermal analysis

Indexed keywords

BENZOIC ACID; CARBOXYLIC ACID DERIVATIVE; CIPROFLOXACIN; CIPROFLOXACIN CITRATE; CIPROFLOXACIN MALONATE; CIPROFLOXACIN TARTRATE; CITRIC ACID; MALONIC ACID; NORFLOXACIN; NORFLOXACIN BENZOATE; NORFLOXACIN OXALATE; NORFLOXACIN TARTRATE; OXALIC ACID; TARTARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CRYSTAL STRUCTURE; DRUG FORMULATION; DRUG SOLUBILITY; HYDRATION; PHASE TRANSITION; PROTON TRANSPORT; STOICHIOMETRY;

EID: 79958855395     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22537     Document Type: Article

References (32)

1. Appelbaum PC, Hunter PA. 2000. The fluoroquinolone antibacterials: Past, present and future perspectives. Int J Antimicrob Agents 16:5-15.
2. Oliphant CM, Green GM. 2002. Quinolones: A comprehensive review. Am Fam Physician 65:455-464.
3. Hu J, Wang W, Zhu Z, Chang H, Pan F, Lin B. 2007. Quantitative structure activity relationship model for prediction of genotoxic potential for quinolone antibacterials. Environ Sci Technol 41:4806-4812.
4. Mazuel C. 1991. Norfloxacin. Anal Profiles Drug Subst 20:557-600.
5. Drlica K, Zhao X. 1997. DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev 61:377-392.
6. Tackás-Novák K, Noszál B, Hermecz I, Kersztúrri G, Podanyi B, Szasz G. 1990. Protonation equilibria of quinolone antibacterials. J Pharm Sci 79:1023-1028.
7. Ross DL, Riley CM. 1990. Aqueous solubilities of some variously substituted quinolone antibacterials. Int J Pharm 63:237-250.
8. Pudipeddi M, Serajuddin ATM, Grant DJW, Stahl PH. 2002. Solubility and dissolution of weak acids, bases, and salts. In: Handbook of pharmaceutical salts, properties, selection and use. Stahl PH, Wermuth CG, Eds. 1st ed. Weinheim: Wiley-VCH, pp19-40.
9. Childs SL, Chyall LJ, Dunlap JT, Smolenskaya VN, Stahly BC, Stahly GP. 2004. Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. Molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids. J Am Chem Soc 126:13335-13342.
10. Banerjee R, Bhatt PM, Ravindra NV, Desiraju GR. 2005. Saccharin salts of active pharmaceutical ingredients, their crystal structures, and increased water solubilities. Cryst Growth Des 5:2299-2309.
11. Black SN, Collier EA, Davey RA, Roberts RA. 2007. Structure, solubility, screening, and synthesis of molecular salts. J Pharm Sci 96:1053-1068.
12. Almarsson Ö, Zaworotko MJ. 2004. Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical cocrystals represent a new path to improved medicines? Chem Commun 1889-1896.
13. Blagden N, de Matas M, Gavan PT, York P. 2007. Crystal engineering of active pharmaceutical ingredients to improve the solubility and dissolution rate of drugs. Adv Drug Del Rev 59:617-630.
14. Berge SM, Bighley LD, Monkhouse DC. 1977. Pharmaceutical salts. J Pharm Sci 66:1-19.
15. Basavoju S, Bostrom D, Velaga SP. 2006. Pharmaceutical cocrystal and salts of norfloxacin. Cryst Growth Des 6:2699-2708.
16. Amidon, GL, Lennernäs, H, Shah, VP, Crison, JR. 1995. A theoretical basis for biopharmaceutic drug classification: The correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res 12:413-420.
17. Breda SA, Jimenez-Kairuz AF, Manzo RH, Olivera ME. 2009. Solubility behavior and biopharmaceutical classification of novel high-solubility ciprofloxacin and norfloxacin pharmaceutical derivatives. Int J Pharm 371:106-113.
18. Katdare AV, Bavitz JF. 1984. Hydrate related dissolution characteristics of norfloxacin. Drug Dev Ind Pharm 10:789-807.
19. Hu T-C, Wang H-L, Chen T-F, Lin S-Y. 2002. Hydration-induced proton transfer in the solid-state of Norfloxacin. J Pharm Sci 91:1351-1357.
20. Sarma B, Nath NK, Bhogala BR, Nangia A. 2009. Synthon competition and cooperation in molecular salts of hydroxy benzoic acids and aminopyridines. Cryst Growth Des 9:1546-1557.
21. Childs SL, Stahly GP, Park A. 2007. The salt-cocrystal continuum: The influence of crystal structure on ionization state. Mol Pharm 4:323-338.
22. Fabbiani FPA, Dittrich B, Florence AJ, Gelbrich T, Hursthouse MB, Kuhs WF, Shankland N, Sowa H. 2009. Crystal structures with a challenge: High-pressure crystallization of ciprofloxacin sodium salts and their recovery to ambient pressure. Cryst Eng Comm 11:1396-1406.
23. Chongcharoen W, Byrn SR, Sutanthavibul N. 2008. Solid state interconversion between anhydrous norfloxacin and its hydrates. J Pharm Sci 97:473-489.
24. Roy S, Goud NR, Babu NJ, Iqbal J, Kruthiventi AK, Nangia A. 2008. Crystal structures of norfloxacin hydrates. Cryst Growth Des 8:4343-4346.
25. Bernstein J, Davis RE, Shimoni L, Chang NL. 1995. Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angew Chem Int Ed Engl 34:1555-1573.
26. Sheldrick GM. 1997. SHELXS-97: Program for crystal structure solution. Gottingen, Germany: University of Göttingen.
27. Sheldrick GM. 1997. SHELXL-97: Program for crystal structure analysis. Gottingen, Germany: University of Göttingen.
28. Bruno IJ, Cole JC, Edgington PR, Kessler MK, Macrae CF, McCabe P, Pearson J, Taylor R. 2002. New software for searching Cambridge structural database and visualising crystal structures. Acta Crystallogr B 58:389-397.
29. Farrugia LJ. 1997. ORTEP-3 for Windows-A version of ORTEP-III with a graphical user interface (GUI). J Appl Crystallogr 30:565.
30. Higuchi T, Connors KA. 1965. Phase-solubility techniques. Adv Anal Chem Instrum 4:117-212.
31. Long M, Chen Y. 2009. Dissolution testing of solid products. In: Developing solid oral dosage forms, pharmaceutical theory and practice. Qiu Y, Chen Y, Zhang GGZ, Eds. 1st ed. Burlington: Elsevier, pp 319-340.
32. World Health Organization. 2003. The International Pharmacopoeia. 3rd ed. Geneva: WHO.