Sildenafil/cyclodextrin complexation: Stability constants, thermodynamics, and guest-host interactions probed by 1H NMR and molecular modeling studies

Journal of Pharmaceutical and Biomedical Analysis

Volumn 41, Issue 3, 2006, Pages 857-865

  Al Omari, Mahmoud M ^a   Zughul, Mohammad B ^b   Davies, J Eric D ^c   Badwan, Adnan A ^a  

^a JORDANIAN PHARMACEUTICAL MANUFACTURING COMPANY   (Jordan)

^b UNIVERSITY OF JORDAN   (Jordan)

^c LANCASTER UNIVERSITY   (United Kingdom)

Author keywords

1H NMR; Cyclodextrin; DSC; Isomeric inclusion complexes; Molecular modeling; Phase solubility diagrams; Sildenafil

Indexed keywords

ANION; CYCLODEXTRIN; PHENYL GROUP; PYRIMIDINONE DERIVATIVE; SILDENAFIL;

ARTICLE; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG STABILITY; ELECTRICITY; ENTHALPY; ENTROPY; IONIZATION; ISOMER; MOLECULAR MODEL; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SOLID STATE; THERMODYNAMICS; X RAY POWDER DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CYCLODEXTRINS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PIPERAZINES; PROTONS; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS; X-RAY DIFFRACTION;

EID: 33646393511     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2006.01.055     Document Type: Article

References (25)

1. Badwan A.A., Nabulsi L., Al Omari M.M., Daraghmeh N., and Ashour M. In: Brittain H.G. (Ed). Sildenafil Citrate Monograph 27 (2001), Academic Press, New York 339-376
2. A. Itoh, T. Niwa, Patent No. WO9,830,209, Application No. WO1997IB01471 19971120, 1998.
3. A. Billotte, P.J. Dunn, B.T. Henry, P.V. Marshall, J.J. Woods, Patent No. EP0,967,214, Application No. EP19990304425 19990608, 1999.
4. A.A. Hussain, L.W. Dittert, Patent No. US6,200,591, Application No. 09/208,439, 2001.
5. W. Tian, J. Langridge, Patent No. WO2,004/017,976, Application No. PCT/GB2003/003636, 2004.
6. F. Vaghefi, M.F. Savitzky, Patent No. US6,849,271, Application No. 274225, 2005.
7. T.A. Ryde, D.C. Hovey, H.W. Bosch, Patent No. US20,050,042,177, Application No. US20040895405 20040721, 2005.
8. R. El-Rashidy, Patent No. US6,087,362, Application No. 09/270,035, 2000.
9. R.R. Vallabhaneni, Patent No. WO01/35926, Application No. PCT/IN00/00105, 2001.
10. Y. Liu, X. Liu, W. Liu, T. Liu, Patent No. CN1,379,047, Application No. CN 2002-116766, 2002.
11. Y. Liu, X. Liu, W. Liu, T. Liu, Patent No. EP1,514,877, Application No. 037298.3, 2005.
12. Higuchi T., and Connors K.A. Adv. Anal. Chem. Instr. In: Reilley C.N. (Ed). Phase Solubility Techniques (1965), Wiley-Intersciences, New York 117-212
13. Zughul M.B., and Badwan A.A. J. Incl. Phenom. 31 (1998) 243-264
14. Taraszewska J., Migut K., and Kozbiat M. J. Phys. Org. Chem. 16 (2003) 121-126
15. Gobry V., Bouchard G., Carrupt P., Testa B., and Girault H. Helv. Chim. Acta. 83 (2000) 1465-1474
16. Lindner K., and Saenger W. Carbohydr. Res. 99 (1982) 103-115
17. Saenger W., Jacob J., Gessler K., Steiner T., Hoffman D., Sanbe H., Koizumi K., Smith S.M., and Takaha T. Chem. Rev. 98 (1998) 1787
18. Tong W., Lach J.L., Chin T., and Guillory J.K. Pharm. Res. 8 (1991) 1307-1312
19. Cooper J.D.H., Muirhead D.C., Taylor J.E., and Baker P.R. J. Chromatogr. B. 701 (1997) 87-95
20. B.N. Nalluri, K.P.R. Chowdary, K.V.R. Murthy, A.R. Hayman, G. Becket. AAPS PharmSciTech. 4 (1) (2003) Article 2 (http://www.pharmscitech.org).
21. Ribeiro L., and Veiga F. J. Incl. Phenom. 44 (2002) 251-256
22. Liu L., and Guo Q.-X. J. Incl. Phenom. 42 (2002) 1-14
23. El-Barghouthi M.I., Masoud N.A., Al-Kafawein J.K., Zughul M.B., and Badwan A.A. J. Incl. Phenom. 53 (2005) 15-22
24. Ventura C.A., Giannone I., Paolino D., Pistara V., Corsaro A., and Puglisi G. Eur. J. Med. Chem. 40 (2005) 624-631
25. Connors K.A. Chem. Rev. 97 (1997) 1325-1357