Liquid-liquid miscibility gaps in drug-water binary systems: Crystal structure and thermodynamic properties of prilocaine and the temperature-composition phase diagram of the prilocaine-water system

Molecular Pharmaceutics

Volumn 10, Issue 4, 2013, Pages 1332-1339

  Rietveld, Ivo B ^a   Perrin, Marc Antoine ^b   Toscani, Siro ^c   Barrio, Maria ^d   Nicolai, Beatrice ^a   Tamarit, Josep Lluis ^d   Ceolin, René ^a,d  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b SANOFI   (France)

^c UNIVERSITÉ DE RENNES 1   (France)

^d UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

Author keywords

crystal structure; EMLA cream; local anesthetic; phase behavior; physical properties; thermodynamics

Indexed keywords

EMLA; LIDOCAINE; PRILOCAINE; WATER;

AQUEOUS SOLUTION; ARTICLE; CALORIMETRY; CHEMICAL COMPOSITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DRUG STABILITY; DRUG STRUCTURE; MISCIBILITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RACEMIC MIXTURE; THERMODYNAMICS; THERMOSTABILITY; X RAY POWDER DIFFRACTION;

ANESTHETICS; ANESTHETICS, LOCAL; CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CHEMISTRY, PHYSICAL; CRYSTALLOGRAPHY, X-RAY; EMULSIONS; LIDOCAINE; PRILOCAINE; SOLVENTS; SURFACE PROPERTIES; TEMPERATURE; THERMODYNAMICS; WATER; X-RAY DIFFRACTION;

EID: 84875771442     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300542k     Document Type: Article

References (26)

1. Brodin, A.; Nyqvist-Mayer, A.; Wadsten, T.; Forslund, B.; Broberg, F. Phase-Diagram and Aqueous Solubility of the Lidocaine Prilocaine Binary-System J. Pharm. Sci. 1984, 73 (4) 481-484
2. Nyqvist-Mayer, A. A.; Brodin, A. F.; Frank, S. G. Phase Distribution Studies on an Oil-Water Emulsion Based on a Eutectic Mixture of Lidocaine and Prilocaine as the Dispersed Phase J. Pharm. Sci. 1985, 74 (11) 1192-1195
3. Nyqvist-Mayer, A. A.; Brodin, A. F.; Frank, S. G. Drug Release Studies on an Oil-Water Emulsion Based on a Eutectic Mixture of Lidocaine and Prilocaine as the Dispersed Phase J. Pharm. Sci. 1986, 75 (4) 365-373
4. Céolin, R.; Barrio, M.; Tamarit, J. L.; Veglio, N.; Perrin, M. A.; Espeau, P. Liquid-liquid Miscibility Gaps and Hydrate Formation in Drug-Water Binary Systems: Pressure-Temperature Phase Diagram of Lidocaine and Pressure-Temperature-Composition Phase Diagram of the Lidocaine-Water System J. Pharm. Sci. 2010, 99 (6) 2756-2765
5. Fournival, J. L.; Rouland, J. C.; Ceolin, R. Polymorphism of barbital and the barbital-water system J. Therm. Anal. 1987, 32 (5) 1547-1557
6. Fournival, J. L.; Rouland, J. C.; Ceolin, R. Phenobarbital-water system J. Therm. Anal. 1988, 34 (1) 161-175
7. Ballon, J.; Comparat, V.; Pouxe, J. The blade chamber-A solution for the curved gaseous detectors Nucl. Instrum. Methods Phys. Res., Sect. A 1983, 217, 213-216
8. Evain, M.; Deniard, P.; Jouanneaux, A.; Brec, R. Potential of the Inel X-Ray Position-Sensitive Detector-a General Study of the Debye-Scherrer Setting J. Appl. Crystallogr. 1993, 26, 563-569
9. Rodriguez-Carvajal, J.; Roisnel, T.; Gonzales-Platas, J. Full-Prof suite version 2005; Laboratoire Léon Brillouin, CEA-CNRS, CEA Saclay: Saclay, France, 2005.
10. Neumann, M. A. X-Cell: a novel indexing algorithm for routine tasks and difficult cases J. Appl. Crystallogr. 2003, 36, 356-365
11. Engel, G. E.; Wilke, S.; Konig, O.; Harris, K. D. M.; Leusen, F. J. J. PowderSolve-a complete package for crystal structure solution from powder diffraction patterns J. Appl. Crystallogr. 1999, 32, 1169-1179
12. Hanson, A. W.; Banner, D. W. 2-Diethylamino-2′,6′- Acetoxylidide (Lidocaine) Acta Crystallogr., B 1974, 30 (Oct 15) 2486-2488
13. Coelho, A. A. TOPAS Academic version 4.1 (Computer Software); Coelho Software: Brisbane, 2007.
14. Dollase, W. A. Correction of Intensities for Preferred Orientation in Powder Diffractometry-Application of the March Model J. Appl. Crystallogr. 1986, 19, 267-272
15. Bruno, I. J.; Cole, J. C.; Kessler, M.; Jie, L.; Motherwell, W. D. S.; Purkis, L. H.; Smith, B. R.; Taylor, R.; Cooper, R. I.; Harris, S. E.; Orpen, A. G. Retrieval of crystallographically-derived molecular geometry information J. Chem. Inf. Comput. Sci. 2004, 44, 2133-2144
16. Neumann, M. A. GRACE (Computer Software); see http://www.avmatsim.eu.
17. Kresse, G.; Furthmüller, J. Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Phys. Rev. B: Condens. Matter 1996, 54, 11169-11186
18. Kresse, G.; Hafner, J. Ab initio molecular dynamics for liquid metals Phys. Rev. B: Condens. Matter 1993, 47, 558-561
19. Kresse, G.; Joubert, D. From ultrasoft pseudopotentials to the projector augmented-wave method Phys. Rev. B: Condens. Matter 1999, 59, 1758-1775
20. Wang, Y.; Perdew, J. P. Correlation hole of the spin-polarized electron gas, with exact small-wave-vector and high-density scaling Phys. Rev. B: Condens. Matter 1991, 44, 13298-13307
21. Neumann, M. A.; Perrin, M.-A. Energy ranking of molecular crystals using density functional theory calculations and an empirical van der Waals correction J. Phys. Chem. B 2005, 109, 15531-15541
22. Van de Streek, J.; Neumann, M. A. Validation of experimental molecular crystal structures with dispersion-corrected density functional theory calculations Acta Crystallogr., B 2010, 66, 544-558
23. Deringer, V. L.; Hoepfner, V.; Dronskowski, R. Accurate Hydrogen Positions in Organic Crystals: Assessing a Quantum-Chemical Aide Cryst. Growth Des. 2012, 12 (2) 1014-1021
24. Naelapaa, K.; van de Streek, J.; Rantanen, J.; Bond, A. D. Complementing high-throughput X-ray powder diffraction data with quantum-chemical calculations: Application to piroxicam form III J. Pharm. Sci. 2012, 101 (11) 4214-4219
25. Würflinger, A. Differential thermal-analysis under high-pressure IV. Low-temperature DTA of solid-solid and solid-liquid transitions of several hydrocarbons up to 3 kbar Ber. Bunsen-Ges. Phys. Chem. 1975, 79 (12) 1195-1201
26. Mahe, N.; Perrin, M.; Barrio, M.; Nicolai, B.; Rietveld, I.; Tamarit, J.; Ceolin, R. Solid-State Studies of the Triclinic (Z ′=2) Antiprotozoal Drug Ternidazole J. Pharm. Sci. 2011, 100 (6) 2258-2266