Studying thermodynamic aspects of sublimation, solubility and solvation processes and crystal structure analysis of some sulfonamides

International Journal of Pharmaceutics

Volumn 334, Issue 1-2, 2007, Pages 115-124

  Perlovich, German L ^a,c   Strakhova, Nadezda N ^a   Kazachenko, Vladimir P ^a   Volkova, Tatyana V ^c   Tkachev, Valery V ^a,b   Schaper, Klaus Jürgen ^d   Raevsky, Oleg A ^a  

^a INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

^b INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

^c INSTITUTE OF SOLUTION CHEMISTRY   (Russian Federation)

^d RESEARCH CENTER BORSTEL   (Germany)

Author keywords

Crystal structure; N (2,3 Dichlorophenyl) benzene sulfonamide; N (2 Chlorophenyl) benzene sulfonamide; N (4 Chlorophenyl) benzene sulfonamide; Solubility; Solvation; Specific and non specific interactions; Sublimation thermodynamics; Transfer process

Indexed keywords

HEXANE; N (2 CHLOROPHENYL)BENZENESULFONAMIDE; N (2,3 DICHLOROPHENYL)BENZENESULFONAMIDE; N (4 CHLOROPHENYL)BENZENESULFONAMIDE; OCTANOL; SOLVENT; SULFONAMIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CALCULATION; CRYSTAL STRUCTURE; DRUG ABSORPTION; DRUG SOLUBILITY; DRUG STRUCTURE; ENTHALPY; EVAPORATION; PRIORITY JOURNAL; SOLVATION; TEMPERATURE DEPENDENCE; THERMODYNAMICS; VAPOR PRESSURE; X RAY DIFFRACTION;

1-OCTANOL; CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; HEXANES; SOLUBILITY; SOLVENTS; SULFONAMIDES; TEMPERATURE; THERMODYNAMICS; WATER; X-RAY DIFFRACTION;

EID: 33947143653     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2006.10.033     Document Type: Article

References (24)

1. Adsmond D.A., and Grant D.J.W. Hydrogen bonding in sulfonamides. J. Pharm. Sci. 90 (2001) 2058-2077
2. Anderson G.W., Faith H.E., Marson H.W., Winnek P.S., and Roblin R.O. Studies in chemotherapy. 6. Sulfanilamido heterocycles. J. Am. Chem. Soc. 64 (1942) 2902-2905
3. Chickos J.S., and Acree Jr. W.E. Enthalpies of sublimation of organic and organometallic compounds. 1910-2001. J. Phys. Chem. Ref. Data. 31 (2002) 537-698
4. Cox J.D., and Pilcher G. Thermochemistry of Organic and Organometallic Compounds (1970), Academic Press, London
5. Crosley M.L., Northey E.H., and Hultquist M.E. Sulfanilamide derivatives. 5. Constitution and properties of 2-sulfanilamidopyridine. J. Am. Chem. Soc. 62 (1940) 372-374
6. Dannenfelser R.-M., and Yalkowsky S.H. Predicting the total entropy of melting: application to pharmaceuticals and environmentally relevant compounds. J. Pharm. Sci. 88 (1999) 722-724
7. Etter M.C. Encoding and decoding hydrogen-bond patterns of organic compounds. Acc. Chem. Res. 23 (1990) 120-126
8. Gutsche K., Schröder E., Rufer C., and Loge O. Neue blutzuckersenkende Benzolsulfonamido-pyrimidine (new blood glucose lowering benzenesulfonamido-pyrimidines). Arzneim.-Forsch./Drug Res. 24 (1974) 1028-1039
9. Korolkovas A. Essentials of Medicinal Chemistry. 2nd ed. (1988), Wiley, New York pp. 699-716
10. Mandell G.L., and Sande M.A. Goodman and Gilman. In: Gilman A., Rall T.W., Nies A.S., and Taylor P. (Eds). The Pharmacological Basis of Therapeutics. 8th ed. vol. 2 (1992), McGraw-Hill, Singapore 1047-1057
11. Martinez F., and Gomez A. Thermodynamic study of the solubility of some sulfonamides in octanol, water, and the mutually saturated solvents. J. Solut. Chem. 30 (2001) 909-923
12. Martinez F., and Gomez A. Thermodynamics of partitioning of some sulfonamides in 1-octanol-buffer and liposome systems. J. Phys. Organ. Chem. 15 (2002) 874-880
13. Martinez F., and Gomez A. Estimation of the solubility of sulfonamides in aqueous media from partition coefficients and entropies of fusion. Phys. Chem. Liquid. 40 (2002) 411-420
14. Perlovich G.L., and Bauer-Brandl A. Solvation of drugs as a key for understanding partitioning and passive transport exemplified by NSAIDs. Curr. Drug Deliv. 1 (2004) 213-226
15. Perlovich G.L., Rodionov S.V., and Bauer-Brandl A. Thermodynamics of solubility, sublimation and solvation processes of parabens. Eur. J. Pharm. Sci. 24 (2005) 25-33
16. Perlovich G.L., Kurkov S.V., and Bauer-Brandl A. The difference between partitioning and distribution from a thermodynamic point of view: NSAIDs as an example. Eur. J. Pharm. Sci. 27 (2006) 150-157
17. Perlovich G.L., and Brandl-Bauer A. Thermodynamics of solutions i: benzoic acid and acetylsalicylic acid as models for drug substances and the prediction of solubility. Pharm. Res. 20 (2003) 471-478
18. Perlovich G.L., Tkachev V.V., Schaper K.-J., and Raevsky O.A. N-(2-Chlorophenyl)benzenesulfonamide. Acta Cryst. E 62 (2006) o780-o782
19. Perlovich G.L., Tkachev V.V., Schaper K.-J., and Raevsky O.A. Determination of the structure of N-(4-chlorophenyl)-benzenesulfonamide. Acta Cryst. E 62 (2006) o376-o378
20. Sheldrick G.M. SHELXL97 and SHELXS97 (1997), University of Göttingen, Germany
21. Tkachev V.V., Schaper K.-J., Strakhova N.N., and Kazachenko V.P. N-(2,3-Dichlorophenyl)benzenesulfonamide. Acta Cryst. E 62 (2006) o2514-o2515
22. Ucucu U., Isikdag I., and Dogu H. Acta Pharm. Turc. 37 (1995) 134
23. Verevkin S.P., and Schick C. Determination of vapor pressures, enthalpies of sublimation, and enthalpies of fusion of benzenetriols. Thermochim. Acta 415 (2004) 35-42
24. Zielenkiewicz W., Perlovich G., and Wszelaka-Rylik M. The vapor pressure and the enthalpy of sublimation determination by inert gas flow-method. J. Therm. Anal. Calorimet. 57 (1999) 225-234