Solubility of antibiotics in different solvents. Part II. non-hydrochloride forms of tetracycline and ciprofloxacin

Industrial and Engineering Chemistry Research

Volumn 47, Issue 21, 2008, Pages 8083-8089

  Caço, Ana I ^a   Varanda, Fátima ^a   De Melo, Maria J Pratas ^a   Dias, Ana M A ^b   Dohrn, Ralf ^c   Marrucho, Isabel M ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF MINHO   (Portugal)

^c BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ETHANOL; SOLUBILITY; SOLVENTS; TERNARY SYSTEMS;

2 PROPANOLS; ACTIVITY COEFFICIENT MODELS; CIPROFLOXACIN; COSMO-RS; DIFFERENT SOLVENTS; EXPERIMENTAL DATUMS; ORDERS OF MAGNITUDES; TEMPERATURE RANGES; UNIQUAC;

ANTIBIOTICS;

EID: 56749146239     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie8003495     Document Type: Article

References (31)

1. Appelbaum, P. C.; Hunter, P. A. The fluoroquinolone antibacterials: past, present and future perspectives. Int. J. Antimicrobial Agents 2000, 16 (1), 5-15.
2. Van Bambeke, F.; Michot, J. M.; Van Eloere, J.; Tulkens, P. M. Quinolones in 2005: an update. Clin. Microbiol. Inf. 2005, 11 (4), 256-280.
3. Gupta, R. B.; Heidemann, R. A. Solubility Models for Amino Acids and Antibiotics. AIChE J. 1990, 36, 333.
4. Yalkowsky, S. H. Estimation of Entropies of Fusion of Organic Compounds. Ind. Eng. Chem. Fundam. 1979, 18, 108.
5. Gmehling, J. G.; Anderson, T. F.; Prausnitz, J. M. Solid-Liquid Equilibria Using UNIFAC. Ind. Eng. Chem. Fundam. 1978, 17, 269.
6. Atík, Z.; Ahlers, J.; Lohmann, J.; Gmehling, J. Binary Solid Liquid Equilibria of N,N-Dimethylacetamide with 1,2-Dichloroethane, Dichloromethane, and 1-Propanol. J. Chem. Eng. Data 2001, 46, 1190.
7. Teodorescu, M.; Wilken, M.; Wittig, R.; Gmehling, J. Azeotropic and Solid-Liquid Equilibria Data for Several Binary Organic Systems Containing One Acetal Compound. Fluid Phase Equilib. 2003, 204, 267.
8. Domanska, U.; Aachwa, J. (Solid + Liquid) Phase Equilibria of Binary Mixtures Containing N-Methyl-2-pyrrolidinone and Alcohol at Atmospheric Pressure. J. Chem. Thermodyn. 2003, 35, 1215.
9. Domanska, U.; Bogel-Aukasik, E. Solid-Liquid Equilibria for Systems Containing 1-Buty1-3-methylimidazolium Chloride. Fluid Phase Equilib. 2004, 218, 123.
10. Gracin, S.; Brinck, T.; Rasmuson, A. C. Prediction of Solubility of Organic Compounds in Solvents by UNIFAC. Ind. Eng. Chem. Res. 2002, 41, 5114.
11. Gracin, S.; Rasmuson, A. C. Solubility of Phenylacetic Acid, p-Hydroxyphenylacetic Acid, p-Hydroxybenzoic Acid, and Ibuprofen in Pure Solvents. J. Chem. Eng. Data 2002, 47, 1379.
12. Sandler, S. I. Chemical and Engineering Thermodynamics, 3rd ed.; John Wiley & Sons: New York, 1999.
13. Prausnitz, J. M.; Lichtenthaler, R. N.; de Azevedo, E. G. Molecular Thermodynamics of Fluid-Phase Equilibria, 3rd ed.; Prentice Hall: Upper Saddle River, NJ, 1999.
14. Feleilnik, L.; Jazbinek, A.; Hvala, A.; Vreer, F.; Klamt, A. Solubility of Sodium Diclofenac in Different Solvents. Fluid Phase Equilib. 2007, 261, 140.
15. Varanda, F.; Melo, M. J.; Caço, A.; Dohrn, R.; Makrydaki, F.; Voutsas, E.; Tassios, D.; Marrucho, I. M. Solubility of Antibiotics in Different Solvents. 1. Hydrochloride Forms of Tetracycline, Moxifloxacin, and Ciprofloxacin. Ind. Eng. Chem. Res. 2006, 45, 6368-6374.
16. Renon, H.; Prausnitz, J. M. Local Compositions in Excess Thermodynamic Functions for Liquid Mixtures. AIChE J. 1968, 14, 135.
17. Abrams, D. S.; Prausnitz, J. M. Statistical Thermodynamics of Liquid Mixtures. A New Expression for the Excess Gibbs Energy of Partly of Completely Miscible Systems. AIChE J. 1975, 21, 116.
18. VTPLAN process simulator, www.bayertechnology.com.
19. Dortmund Data Bank. http://www.ddbst.de/new/Default.htm.
20. Poling, B. E.; Prausnitz, J. M.; O'Connell, J. P. The Properties of Gases and Liquids, 5th ed.; McGraw Hill: New York, 2001.
21. CAPEC database. http://www.capec.kt.dtu.dk/, Lynsby, Denmark.
22. O'Neil, M. J., Heckelman, P. E. C. B., Koch, C. B., Roman, K. J. Eds.; Merck Index, 14th ed.; Merck Publishing Group, 2006.
23. Dorofeev, V. L.; Arzamastsev, A. P.; Veselova, O. M. Melting Point Determination for the Analysis of Drugs of the Fluoroquinolone Group. Pharm. Chem. J. 2004, 38, 333.
24. Tsonopoulos, C.; Prausnitz, J. M. Activity Coefficients of Aromatic Solutes in Dilute Aqueous Solutions. Ind. Eng. Chem. Fundam. 1971, 10, 593.
25. DIPPR database. http://dippr.byu.edu/.
26. Klamt, A.; Eckert, F.; Hornig, M.; Beck, M. E.; Burger, T. Prediction of Aqueous Solubility of Drugs and Pesticides with COSMORS. J. Comput. Chem. 2002, 23 (2), 275-281.
27. Pavelka, M.; Lucas, M. F. A.; Russo, N. On the Hydrolysis Mechanism of the Second-Generation Anticancer Drug Carboplat. Chem.-Eur. J. 2007, 13 (36), 10108-10116.
28. Stezowski, J. J. Chemical-Structural Properties of Tetracycline Derivates. I. Molecular Structure and Conformation of the Free Base Derivatives. J. Am. Chem. Soc. 1976, 98, 6012.
29. Othersen, O. G.; Waibel, R.; Lanig, H.; Gmeiner, P.; Clark, T. SCRS-DFT and NMR Comparison of Tetracyline and 5a,6-Anhydrotetracyline in Solution. J. Phys. Chem. B 2006, 110, 24766-24774.
30. Othersen, O. G.; Beierlein, F.; Lanig, H.; Clark, T. Conformations and Tautomers of Tetracycline. J. Phys. Chem. B 2003, 107, 13743-13749.
31. Sun, J.; Sakai, S.; Tauchi, Y.; Deguchi, Y.; Chen, J.; Zhang, R.; Morimoto, K. Determination of Lipophilicity of Two Quinolone Antibacterials, Ciprofloxacin and Grepafloxacin, in the Protonation Equilibrium. Eur. J. Pharm. Biopharm. 2002, 54 (1), 51-58.