Solubilization of two structurally related anticancer drugs: XK-469 and PPA

Journal of Pharmaceutical Sciences

Volumn 95, Issue 1, 2006, Pages 97-107

  He, Yan ^a   Tabibi, S Esmail ^b   Yalkowsky, Samuel H ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Combination; Complexation; Cosolvency; Excipients; Formulation vehicle; pH adjustment; PPA; Solubility; Surfactant; XK 469

Indexed keywords

2 PHENOXYPROPANOIC ACID; 2 [4 (7 CHLORO 2 QUINOXALINYL)OXYL]PHENOXYPROPANOIC ACID; ANTINEOPLASTIC AGENT; EXCIPIENT; PROPIONIC ACID DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG; XK 469; 2 HYDROXYPROPYL BETA CYCLODEXTRIN; 2-HYDROXYPROPYL-BETA-CYCLODEXTRIN; 2-PHENOXYPROPANOIC ACID; ALCOHOL; BETA CYCLODEXTRIN DERIVATIVE; POLYSORBATE; PROPYLENE GLYCOL; SBE4 BETA CYCLODEXTRIN; SBE4-BETA-CYCLODEXTRIN; SOLVENT; SURFACTANT;

ARTICLE; COMPLEX FORMATION; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STRUCTURE; MICELLE; PH; PKA; TECHNIQUE; CHEMISTRY; COMPARATIVE STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLUBILITY;

ANTINEOPLASTIC AGENTS; BETA-CYCLODEXTRINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ETHANOL; HYDROGEN-ION CONCENTRATION; MICELLES; POLYSORBATES; PROPIONATES; PROPYLENE GLYCOL; QUINOXALINES; SOLUBILITY; SOLVENTS; SURFACE-ACTIVE AGENTS;

EID: 33645238997     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20500     Document Type: Article

References (24)

1. Gribbon P, Andreas S. 2005. High-throughput drug discovery: What can we expect from HTS? Drug Discov Today 10:17-22.
2. Corbett TH, LoRusso P, Demchick L, Simpson C, Pugh S, White K, Kushner J, Polin L, Meyer J, Czarnecki J, Heilbrun L, Horwitz JP, Gross JL, Behrens CH, Harrison BA, McRipley RJ, Trainor G. 1998. Preclinical antitumor efficacy of analogs of XK469: Sodium-(2-[4-(7-chloro-2-quinoxalinyloxy)-phenoxy]propionate. Investig New Drugs 16:129-139.
3. LoRusso PM, Parchment R, Demchik L, Knight J, Polin L, Dzubow J, Behrens C, Harrison B, Trainor G, Corbett TH. 1998. Preclinical antitumor activity of XK469 (NSC 656889). Investig New Drugs 16:287-296.
4. Ding Z, Zhou J-Y, Wei W-Z, Baker W, Wu GS. 2002. Induction of apoptosis by the new anticancer drug XK469 in human ovarian cancer cell lines. Oncogene 21:4530-4538.
5. Higuchi T, Connors KA. 1965. Phase-solubility techniques. Advan Anal Chem Instr 4:117-212.
6. Yalkowsky SH. 1999. Solubility and solubilization in aqueous media. New York: Oxford University Press.
7. Yalkowsky SH, Flynn GL, Amidon GL. 1972. Solubilization of nonelectrolytes in polar solvents. J Pharm Sci 61:983-984.
8. Yalkowsky SH, Rubino JT. 1985. Solubilization by cosolvents: I. Organic solutes in propylene glycol-water mixture. J Pharm Sci 74:416-421.
9. Li P, Tabibi SE, Yalkowsky SH. 1998. Combined effect of complexation and pH on solubilization. J Pharm Sci 87:1535-1537.
10. Li P, Tabibi SE, Yalkowsky SH. 1999. Solubilization of ionized and unionized flavopiridol by ethanol and polysorbate 20. J Pharm Sci 88:507-509.
11. Li P, Tabibi SE, Yalkowsky SH. 1999. Solubilization of flavopiridol by pH combined with cosolvents, surfactants, and complexants. J Pharm Sci 88:945-947.
12. Millard JW, Alvarez-Núñez FA, Yalkowsky SH. 2002. Solubilization by cosolvents establishing useful constants for the log-linear model. Int J Pharm 245:153-166.
13. Powell MF, Nguyen T, Baloian L. 1998. Compendium of excipients for parenteral formulations PDA. J Pharm Sci Tech 52:238-311.
14. Collete JH, Koo L. 1975. Interaction of substituted Benzoic acid derivatives with Polysorbate 20 Micelles. J Pharm Sci 64:1253-1255.
15. Tomida H, Yotsuyanagi T, Ikeda K. 1978. Solubilization of benzoic acid derivatives by polyoxyethylene lauryl ether. Chem Pharm Bull 26:2821-2831.
16. Alvarez-Nunez FA, Yalkowsky SH. 2000. Relationship between Polysorbate 80 solubilization descriptors and octanol-water partition coefficients of drugs. Int J Pharm 200:217-222.
17. Jinno J, Oh D-M, Crison JR, Amidon GL. 2000. Dissolution of ionizable water-insoluble drugs: The combined effect of pH and surfactant. J Pharm Sci 89:268-274.
18. Tinwalla AY, Hoesterey BL, Xiang TX, Lim K, Anderson BD. 1993. Solubilization of thiazolobenzimidazole using a combination of pH adjustment and complexation with 2-hydroxypropyl-beta-cyclodextrin. Pharm Res 10:1136-1143.
19. Johnson MD, Hoesterey BL, Anderson BD. 1994. Solubilization of a tripeptide HIV protease inhibitor using a combination of ionization and complexation with chemically modified cyclodextrins. J Pharm Sci 83:1142-1146.
20. Okimoto K, Rajewski RA, Uekama K, Jona JA, Stella VJ. 1996. The interaction of charged and uncharged drugs with neutral (HP-β-CD) and anionically charged (SBE7-β-CD) β-cyclodextrins. Pharm Res 13:256-264.
21. 7M-β-CD to HP-β-CD. Pharm Res 18:667-673.
22. Matsui X, Mochida K. 1979. Binding forces contributing to the association of cyclodextrin with alcohol in an aqueous solution. Bull Chem Soc Jpn 52:2808-2814.
23. Uekama K, Ikeda Y, Hirayama F, Shibata M. 1980. Inclusion complexation of p-hydroxybenzoic acid esters with alpha- and beta-cyclodextrins: Dissolution behaviors and antimicrobial activities. Yakugaku Zasshi 100:994-1003.
24. Uekama K. 1981. Pharmaceutical applications of cyclodextrin complexation. Yakugaku Zasshi 101:857-873.