Photodegradation of Moxifloxacin in Aqueous and Organic Solvents: A Kinetic Study

Ageing International

Volumn 15, Issue 6, 2014, Pages 1588-1597

  Ahmad, Iqbal ^a   Bano, Raheela ^a   Musharraf, Syed Ghulam ^b   Ahmed, Sofia ^a   Sheraz, Muhammad Ali ^a   ul Arfeen, Qamar ^b   Bhatti, Muhammad Salman ^b   Shad, Zufi ^a  

^a BAQAI MEDICAL UNIVERSITY   (Pakistan)

^b UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

acid base catalysis; kinetics; moxifloxacin; photodegradation; rate pH profile; solvent effect

Indexed keywords

ANTIINFECTIVE AGENT; MOXIFLOXACIN; ORGANIC COMPOUND; QUINOLONE DERIVATIVE; SOLVENT;

CHEMICAL MODEL; CHEMISTRY; DRUG STABILITY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; LIGHT; MEDICINAL CHEMISTRY; PH; PHARMACEUTICS; PHOTOLYSIS; PROCEDURES; RADIATION RESPONSE; REPRODUCIBILITY; STATISTICAL MODEL; TANDEM MASS SPECTROMETRY; VALIDATION STUDY; VISCOSITY;

ANTI-BACTERIAL AGENTS; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; FLUOROQUINOLONES; HYDROGEN-ION CONCENTRATION; KINETICS; LIGHT; LINEAR MODELS; MODELS, CHEMICAL; ORGANIC CHEMICALS; PHOTOLYSIS; REPRODUCIBILITY OF RESULTS; SOLVENTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; TECHNOLOGY, PHARMACEUTICAL; VISCOSITY;

EID: 84912107527     PISSN: 01635158     EISSN: 1936606X     Source Type: Journal    
DOI: 10.1208/s12249-014-0184-x     Document Type: Article

References (57)

1. Sweetman SC. The complete drug reference. 36th ed. London: Pharmaceutical Press; 2009. p. 302.
2. British Pharmacopoeia. Monograph on moxifloxacin. London: Her Majesty’s Stationary Office; 2013. Electronic version.
3. O’Neil MJ. The Merck Index. 15th ed. Cambridge: The Royal Society of Chemistry; 2013. p. 1171.
4. Appelbaum PC, Hunter PA. The fluoroquinolone antibacterials: past, present and future perspective. Int J Antimicrob Agents. 2000;16:5–15.
5. Eliopulos GM. Activity of newer fluoroquinolones in vitro against gram-positive bacteria. Drugs. 1999;58:23–8.
6. Sharma SK, George N, Kdhiravan T, Saha PK, Mishra HK, Hanif M. Prevalence of extensively drug resistant tuberculosis among patients with multidrug-resistant tuberculosis: a retrospective hospital-based study. Indian J Med Res. 2009;130:392–5.
7. Soni K. Fluoroquinolones: chemistry & action—a review. Indo Glob J Pharm Sci. 2012;2:43–53.
8. Maruri F, Sterling TR, Kaiga AW, Blackman A, Vander Heigden YF, Mayer C, et al. A systematic review of gyrase mutations associated with fluoroquinolone-resistant Mycobacterium tuberculosis and a propose gyrase numbering system. J Antimicrob Chemother. 2012;67:819–31.
9. Tarkase KN, Admane SS, Sonkhede NG, Shejwal SR. Development and validation of UV spectrophotometric methods for determination of moxifloxacin HCl in bulk and pharmaceutical formulations. Der Pharma Chemica. 2012;4:1180–5.
10. De Guidi G, Giuffrida S, Monti S, Pisu PS, Sortino S, Costanzo LL. Molecular mechanism of phtosensitization induced by drugs XIV: two different behaviors in the photochemistry and photosensitization of antibacterials containing a fluoroquinolone like chromophore. Int J Photoenergy. 1999;1:1–6.
11. Viola G, Facciola L, Canton M, Vedaldi D, Acqua FD, Aloisi GG, et al. Photophysical and phototoxic properties of the antibacterial fluoroquinolones levofloxacin and moxifloxacin. Chem Biodivers. 2004;1:782–800.
12. Hidalgo ME, Pessoa C, Fernandez E, Cardenas AM. Comparative determination 232 of photodegradation kinetics of quinolones. J Photochem Photobiol A Chem. 1993;73:135–8.
13. Burhenne J, Ludwig M, Spiteller M. Polar photodegradation products of quinolones determined by HPLC/MS/MS. Chemosphere. 1999;38:1279–86.
14. Kummerer K. Antibiotics in the aquatic environment—a review—part I. Chemosphere. 2009;75:417–34.
15. United States Pharmacopoeia 30–National Formulary 25. Rockville, MD, USA: United States Pharmacopoeial Convention, Inc., Electronic version; 2007.
16. Lorenzo F, Navaratnam S, Edge R, Allen NS. Primary photophysical properties of moxifloxacin—a fluoroquinolone antibiotic. Photochem Photobiol. 2008;84:1118–25.
17. Doorslaer XV, Demeestere K, Heynderickx PM, Langenhove HV, Dewulf J. UV-A and UV-C induced photolytic and photocatalytic degradation of aqueous ciprofloxacin and moxifloxacin: reaction kinetics and role of adsorption. Appl Catal B Environ. 2011;101:540–7.
18. Sturini M, Speltini A, Maraschi F, Profumo A, Pretali L, Irastorza EA, et al. Photolytic and photocatalytic degradation of fluoroquinolones in untreated river water under natural sunlight. Appl Catal B Environ. 2012;119–120:32–9.
19. Hubicka U, Zmudzki P, Talik P, Zuromska BW, Krzek J. Photodegradation assessment of ciprofloxacin, moxifloxacin, norfloxacin and ofloxacin in the presence of excipients from tablets by UPLC-MS/MS and DSC. J Chem Cent. 2013;7:1–12.
20. Torniainen K, Tammilehto S, Ulvi V. The effect of pH, buffer type and drug concentration on the photodegradation of ciprofloxacin. Int J Pharm. 1996;132:53–61.
21. Burhenne J, Ludwig M, Nikoloudis P, Spiteller M. Photolytic degradation of fluoroquinolone carboylic acid in aqueous solution. Part I: primary photoproducts and halflives. Environ Sci Pollut Res. 1997;4:10–5.
22. Burhenne J, Ludwig M, Spiteller M. Photolytic degradation of fluoroquinolone carboylic acid in aqueous solution. Part II: isolation and structural elucidation of polar photometabolities. Environ Sci Pollut Res. 1997;4:61–7.
23. Lovdahl MJ, Priebe SR. Characterization of clinafloxacin photodegradation products by LC-MS/MS andNMR. J Pharm Biomed Anal. 2000;23:521–34.
24. Salgado HRN, Moreno PRH, Braga AL, Schapoval EES. Photodegradation of sparfloxacin 259 and isolation of its degradation products by preparative HPLC. Rev Cienc Farm Basica Apl. 2005;26:47–54.
25. Motwani SK, Khar RK, Ahmad FJ, Chopra S, Kohli K, Talegaonkar S, et al. Stability indicating high performance thin-layer chromatographic determination of gatifloxacin as bulk drug and form polymeric nanoparticles. Anal Chim Acta. 2006;576:253–60.
26. Budai M, Grof P, Zimmer A, Papai K, Klebovich I, Ludanyi K. UV light induced photodegradation of liposomes encapsulated fluoroquinolones. J Photochem Photobiol A Chem. 2008;198:268–73.
27. Wang J, Li W, Li C-G, Hu Y-Z. Photodegradation of fleroxacin injection: different products with different concentration levels. AAPS PharmSciTech. 2011;12:872–8.
28. Ahmad I, Bano R, Sheraz MA, Ahmed S, Mirza T, Ansari SA. Photodegradation of levofloxacin in aqueous and organic solvents: a kinetic study. Acta Pharma. 2013;63:221–7.
29. Hutchinson DJ, Johnson CE, Klein KC. Stability of extemporaneously prepared moxifloxacin oral suspensions. Am J Health Syst Pharm. 2009;66:665–7.
30. Kumar MT, Srikanth G, Rao JV, Rao KS. Development and validation of HPLC-UV method for the estimation of levofloxacin in human plasma. Int J Pharm Pharm Sci. 2011;3:247–50.
31. Rama Subbaiah P, Kumudhavalli MV, Saravanan C, Kumar M, Chandira RM. Method development and validation for estimation of moxifloxacin HCl in tablet dosage form by RP-HPLC method. Pharm Anal Acta. 2010;1:1–2.
32. Sultana N, Arayne MS, Akhtar M, Shamim S. High-performance liquid chromatography assay for moxifloxacin in bulk, pharmaceutical formulations and serum: application to in-vitro metal interactions. J Chin Chem Soc. 2010;57:1–10.
33. Dewani AP, Barik BB, Kanungo SK, Wattyani BR, Chandewar AV. Development and validation of RP-HPLC method for the determination of moxifloxacin in presence of its degradation products. Am-Eurasian J Sci Res. 2011;6:192–200.
34. Kunagu VS, Janardhan M. Development and validation of stability-indicating RP-HPLC method for estimation of moxifloxacin in moxifloxacin HCl tablets. Int J Pharm Invent. 2012;2:24–33.
35. Wang N, Zhu L, Zhao X, Yang W, Sun H. Improved HPLC method for the determination 285 of moxifloxacin in application to a pharmacokinetics study in patients with infectious diseases. ISRN Pharmacol. 2013;2013:1–7.
36. Motwani SK, Khar RK, Ahmad FJ, Chopra S, Kohli K, Talegaonkar S. Application of a validated stability indicating densitometric thin-layer chromatographic method to stress degradation studies on moxifloxacin. Anal Chim Acta. 2007;582:75–82.
37. Devi ML, Chandrasekhar KB. A validated, specific stability-indicating RP-LC method for moxifloxacin and its related substances. Chromatographia. 2009;69:993–9.
38. Hatchard CG, Parker CA. A new sensitive chemical actinometer. II. Potassium ferrioxalate as a standard chemical actinometer. Proc R Soc Lond A. 1956;235:518–36.
39. Ahmed S, Sheraz MA, Yorucu C, Rehman IU. Quantitative determination of tolfenamic acid and its pharmaceutical formulation using FTIR and UV spectrometry. Cent Eur J Chem. 2013;11:1533–41.
40. Finholt P, Jurgensen G, Kristiansen H. Catalytic effect of buffers on degradation of penicillin G in aqueous solution. J Pharm Sci. 1965;54:387–93.
41. Connors KA, Amidon CL, Stella VJ, editors. Chemical stability of pharmaceuticals: a hand book for pharmacists. 2nd ed. New York: Wiley; 1986. p. 198–207. 250–256.
42. Zia H, Teharan M, Zargarbashi R. Kinetics of carbenicillin degradation in aqueous solution. Can J Pharm Sci. 1974;9:112–7.
43. Schwartz MA, Bara E, Rubycz I, Granatek AP. Stability of methacillin. J Pharm Sci. 1965;54:149–50.
44. Maulding HV, Nazareno JP, Pearson JE, Michaelis AF. Practical kinetics III: benzodiazepine hydrolysis. J Pharm Sci. 1975;64:278–84.
45. Mollica JA, Rehm CR, Smith JB, Govan HK. Hydrolysis of benzothiadiazines. J Pharm Sci. 1971;57:1380–4.
46. Notari RE, Caiola SM. Catalysis of streptovitacin A dehydration: kinetics and mechanism. J Pharm Sci. 1969;58:1203–8.
47. Garrett ER, Seyda K. Prediction of stability in pharmaceutical preparations XX: stability evaluation and bioanalysis of cocaine and benzoylecgonine by high performance liquid chromatography. J Pharm Sci. 1983;72:258–71.
48. Notari RE, Chin ML, Wittebort R. Arabinosylcytosine stability in aqueous solution: 313 pH profile and shelf life productions. J Pharm Sci. 1972;61:1189–96.
49. Hamilton-Miller JMT. The effect of pH and of temperature on the stability and bioactivity of nystatin and amphotericin B. J Pharm Pharmacol. 1973;25:401–7.
50. Notari RE, DeYoung JL. Kinetics and mechanisms of degradation of the antileukemic agent 5-azacytidine in aqueous solution. J Pharm Sci. 1975;64:1148–57.
51. Langlois M-H, Montagut M, Dubost J-P, Grellet J, Saux M-C. Protonation equilibrium and lipophilicity of moxifloxacin. J Pharm Biomed Anal. 2005;37:389–93.
52. Lemaire S, Tulkens PM, Bambeke FV. Contrasting effects of acidic pH on the extracellular and intracellular activities of the anti-gram-positive flouroquinolones moxifloxacin and delafloxacin against Staphylococcus aureus. Antimicrob Agents Chemother. 2011;55:649–58.
53. Nangia A, Lam F, Hung CT. A stability of aqueous solution of norfloxacin. Drug Dev Ind Pharm. 1991;17:681–94.
54. Hubicka U, Krzek J, Zuromska B, Walczak M, Zylewski M, Pawlowski D. Determination of photostability and photodegradation products of moxifloxacin in the presence of metal ions in solutions and solid phase. Kinetics and identification of photoproducts. Photochem Photobiol Sci. 2012;11:351–7.
55. Park HR, Kim TH, Bark KM. Physicochemical properties of quinolone antibiotics in various environments. Eur J Med Chem. 2002;37:443–60.
56. Ahmad I, Tollin G. Solvent effects on flavin electron transfer reactions. Biochemistry. 1981;20:5925–8.
57. Ahmad I, Fasihullah Q, Vaid FHM. Photolysis of formylmethylflavin in aqueous and organic solvents. Photochem Photobiol Sci. 2006;5:680–5.