Lipophilicity measurement of drugs by reversed phase HPLC over wide pH range using an alkaline-resistant silica-based stationary phase, XBridge™ shield RP18

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 10, 2008, Pages 1417-1422

  Liu, Xiangli ^a   Hefesha, Hossam ^a   Tanaka, Hideji ^b   Scriba, Gerhard ^a   Fahr, Alfred ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Linear solvation free energy relationship; Lipophilicity; Partition coefficient; Reversed phase HPLC

Indexed keywords

ACETYLSALICYLIC ACID; ACID; ACRIDINE; BASE; ESTRADIOL; FLURBIPROFEN; HYDROCORTISONE; INDOMETACIN; KETOPROFEN; MEFENAMIC ACID; METOPROLOL; NAPROXEN; OCTANOL; PENBUTOLOL; PHENAZONE; PHENYLBUTAZONE; PHENYTOIN; PINDOLOL; PROGESTERONE; PROMETHAZINE; PROPRANOLOL; SILICON DIOXIDE; SULFABENZAMIDE; SULFACETAMIDE; SULFADIMIDINE; SULFAMETHOXAZOLE; SULFAMETHOXYPYRIDAZINE; SULFANILAMIDE; TESTOSTERONE; UNINDEXED DRUG;

ACCURACY; ACIDITY; ALKALINITY; ARTICLE; CALCULATION; CORRELATION ANALYSIS; DRUG STRUCTURE; HYDROPHOBICITY; LINEAR SOLVATION FREE ENERGY RELATIONSHIP; LIPOPHILICITY; MEASUREMENT; PARAMETER; PARTITION COEFFICIENT; PH; REPRODUCIBILITY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TECHNIQUE;

1-OCTANOL; ALGORITHMS; ALKALIES; CHEMISTRY, PHYSICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; LIPIDS; ORGANOSILICON COMPOUNDS; PHARMACEUTICAL PREPARATIONS; SILICON DIOXIDE; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 54349089135     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.1417     Document Type: Article

References (38)

1. van de Waterbeemd H., Testa B., "Advances in Drug Research," Vol. 16, ed. by Testa B., Academic Press, London, 1987, pp. 87-227.
2. Hansch C., Leo A., "Substituent Constants for Correlation Analysis in Chemistry and Biology," John Wiley and Sons, New York, 1979.
3. Komiya I., Park J. Y., Kamani A., Ho N. F. H., Higuchi W. I., Int. J. Pharm., 4, 249-262 (1980).
4. Taylor D. C., Pownall R., Burke W., J. Pharm. Pharmacol., 37, 280-283 (1985).
5. Levin V. A., J. Med. Chem., 23, 682-684 (1980).
6. Artursson P., J. Pharm. Sci., 79, 476-482 (1990).
7. Buur A., Trier L., Magnusson C., Artursson P., Int. J. Pharm., 129, 223-231 (1996).
8. Yamagami C., Yokota M., Takao N., Chem. Pharm. Bull., 42, 907-912 (1994).
9. Klein W., Kördel W., Weiss M., Poremski H. J., Chemosphere, 17, 361-386 (1988).
10. Yamagami C., Ogura T., Takao N., J. Chromatogr., 514, 123-136 (1990).
11. El Tayar N., van de Waterbeemd H., Testa B., J. Chromatogr., 320, 305-312 (1985).
12. Braumann T., J. Chromatogr., 373, 191-225 (1986).
13. Belsner K., Pfeifer M., Wilffert B., J. Chromatogr., 629, 123-134 (1993).
14. El Tayar N., van de Waterbeemd H., Testa B., Quant. Struct.-Act. Relat., 4, 69-77 (1985).
15. Lombardo F., Shalaeva M. Y., Tupper K. A., Gao F., Abraham M. H., J. Med. Chem., 43, 2922-2928 (2000).
16. Schoenmaker P. J., Billiet H. A. H., De Galan L., J. Chromatogr., 185, 179-195 (1979).
17. Braumann T., Weber G., Grimme L. H., J. Chromatogr., 263, 329-343 (1983).
18. El Tayar N., van de Waterbeemd H., Testa B., J. Chromatogr., 320, 293-304 (1985).
19. Lambert W. J., J. Chromatogr., 656, 469-484 (1993).
20. van de Waterbeemd H., Kansy M., Wagner B., Fischer H., "Lipophilicity in Drug Action and Toxicology," ed. by Pliska V., Testa B., van de Waterbeemd H., VCH Publishers, Weinheim, 1996, pp. 73-87.
21. Liu X., Tanaka H., Yamauchi A., Testa B., Chuman H., Helv. Chim. Acta, 87, 2866-2876 (2004).
22. Liu X., Tanaka H., Yamauchi A., Testa B., Chuman H., J. Chromatogr. A, 1091, 51-59 (2005).
23. Kaliszan R., Quant. Struct.-Act. Relat., 9, 83-87 (2003).
24. Wyndham K. D., O'Gara J. E., Walter T. H., Glose K. H.,. Lawrence N. L., Alden B. A., Izzo G. S., Hudalla C. J., Iraneta P. C., Anal. Chem., 75, 6781-6788 (2003).
25. Tan L. C., Carr P. W., Abraham M. H., J. Chromatogr. A, 752, 1-18 (1996).
26. Abraham M. H., Rosés M., Poole C. F., Poole S. K., J. Phys. Org. Chem., 10, 358-368 (1997).
27. Kaliszan R., Van Straten M. A., Markuszewski M., Cramers C. A., Claessens H. A., J. Chromatogr. A, 855, 455-486 (1999).
28. Sandi A., Szepesy L., J. Chromatogr. A, 818, 1-17 (1998).
29. Sandi A., Szepesy L., J. Chromatogr. A, 818, 19-30 (1998).
30. Meindl W. R., Von Angerer E., Schönenberger H., Ruckdeschel G., J. Med. Chem., 27, 1111-1118 (1984).
31. Kamlet M. J., Doherty R. M., Abraham M. H., Marcus Y., Taft R. W., J. Phys. Chem., 92, 5244-5255 (1988).
32. El Tayar N., Tsai R. S., Testa B., Carrupt P. A., Leo A., J. Pharm. Sci., 80, 590-598 (1991).
33. Steyaert G., Lisa G., Gaillard P., Boss P., Reymond F., Girault H. H., Carrupt P. A., Testa B., J. Chem. Soc., Faraday Trans., 93, 401-406 (1997).
34. Liu X., Bouchard G., Muller N., Galland A., Girault H. H., Testa B., Carrupt P. A., Helv. Chim. Acta, 86, 3533-3547 (2003).
35. Taillardat-Bertschinger A., Marca Martinet C. A., Carrupt P. A., Reist M., Caron G., Fruttero R., Testa B., Pharm. Res., 19, 729-737 (2002).
36. Stella C., Galland A., Liu X., Teata B., Rudaz S., Veuthey J. C., Carrupt P. A., J. Sep. Sci., 28, 2350-2362 (2005).
37. Geinoz S, "Ph. D. Thesis," University of Lausanne, 2002.
38. Bioloom version 1 from Biobyte Corporation, Clarement, CA.