Solubility of lovastatin in a family of six alcohols: Ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, and 1-octanol

International Journal of Pharmaceutics

Volumn 359, Issue 1-2, 2008, Pages 111-117

  Nti Gyabaah, J ^a,b   Chmielowski, R ^b   Chan, V ^c   Chiew, Y C ^a  

^a The State University of New Jersey   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c Nanyang Technological University   (Singapore)

Author keywords

Alcohols; Lovastatin; Pharmaceutical; Solubility; Statins; Temperature

Indexed keywords

ALCOHOL; BUTANOL; HEXANOL; MEVINOLIN; OCTANOL; PENTANOL; PROPANOL;

ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG ACTIVITY; DRUG SOLUBILITY; DRUG STRUCTURE; ENTHALPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MELTING POINT; PRIORITY JOURNAL; THERMAL ANALYSIS; THERMODYNAMICS;

ALCOHOLS; CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROXYMETHYLGLUTARYL-COA REDUCTASE INHIBITORS; LOVASTATIN; SOLUBILITY; SOLVENTS; TEMPERATURE; THERMODYNAMICS; TRANSITION TEMPERATURE;

EID: 44749093033     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2008.03.046     Document Type: Article

References (40)

1. Adjei A., Newburger J., and Martin A. Extended Hildebrand approach: solubility of caffeine in dioxane-water mixtures. J. Pharm. Sci. 69 (1980) 659-661
2. Alsenz J., Meister E., and Haenel E. Development of a partially automated solubility screening (PASS) assay for early drug development. J. Pharm. Sci. 96 (2007) 1748-1762
3. Apelblat A., and Manzurola E. Solubilities of o-acetylsalicylic 4-aminosalicylic 3,5-dinitrosalicylic, and p-toluic acid, and magnesium-dl-aspartate in water from T = (278 to 348) K. J. Chem. Thermodyn. 31 (1999) 85-91
4. Elder J.P. Thermal behavior of lovastatin. Thermochim. Acta 134 (1988) 41-45
5. Frank T.C., Downey J.R., and Gupta S.K. Quickly screen solvents for organic solids. J. Chem. Eng. Prog. 95 12 (1999) 41-61
6. Gracin S., Brinck T., and Rusmuson A. Prediction of solubility of solid organic compounds in solvents by UNIFAC. Ind. Eng. Chem. Res. 41 (2002) 5114-5124
7. Greenberg W.A., Varvak A., Hanson S.R., Wong K., Huang H., Chen P., and Burk M.J. Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates. PNAS 101 (2004) 5788-5793
8. Herrador M.A., and Gonzalez A.G. Solubility prediction of caffeine in aqueous N,N-dimethylformamide mixtures using the extended Hildebrand solubility approach. Int. J. Pharm. 156 (1997) 239-244
9. Huang Z., Sun G.B., Chiew Y.C., and Kawi S. Formation of ultrafine aspirin particles through rapid expansion of supercritical solutions (RESS). Powder Technol. 160 (2005) 127-134
10. Istvan E.S., and Deisenhofer J. Structural mechanism for statin inhibition of HMG-CoA reductase. Science 292 (2001) 1160-1164
11. Javernik S., Kreft S., Strukelj B., and Vrecer F. Comparison of CE and HPLC methods for determining lovastatin and its oxidation products after exposure to an oxidative atmosphere. Croat. Chem. Acta 76 (2003) 263-268
12. Jiang Q., Gao G.-H., Yu Y.-X., and Qin Y. Solubility of sodium dimethyl isophthalate-5-sulfonate in water and in water + methanol containing sodium sulfate. J. Chem. Eng. Data 45 (2000) 292-294
13. Jouyban A., Khoubnasabjafari M., Chan H.K., Clark B.J., and Acree Jr. W.E. Solubility prediction of anthracene in mixed solvents using a minimum number of experimental data. Chem. Pharm. Bull. 50 (2002) 21-25
14. Jouyban A., Romero S., Chan H., Clark B., and Bustamante P. A co-solvency model to predict solubility of drugs at several temperatures from a limited number of solubility measurements. Chem. Pharm. Bull. 50 (2002) 594-599
15. Jouyban A., Barzegar-Jalali M., and Acree Jr. W.E. Solubility correlation of structurally related drugs in binary solvent mixtures. Int. J. Pharm. 16 (1998) 205-209
16. Kim D.Y., Bochar D.A., Stauffacher C.V., and Rodwell V.W. Expression and characterization of the HMG-CoA reductase of the thermophilic archaeon sulfolobus solfataricus. Protein Expr. Purif. 17 (1999) 435-445
17. Kolar P., Shen J.W., Tsuboi A., and Ishikawa T. Solvent selection for pharmaceuticals. Fluid Phase Equilib. 194 (2002) 771-782
18. Liu B.S., Gong J.B., Wang J.K., and Jia C.Y. Solubility of potassium clavulate in ethanol, 1-1-propanol, and 2-methyl-1-1-propanol between 273 K and 305 K. J. Chem. Eng. Data 50 (2005) 1684-1686
19. Manzoni M., Rollini M., and Bergomi S. Production and purification of statins from Aspergillus terreus strains. Biotechnol. Tech. 12 (1998) 529-532
20. Mirmehrabia M., Rohani S., Murthy K.S.K., and Radatusb B. Solubility, dissolution rate and phase transition studies of ranitidine hydrochloride tautomeric forms. Int. J. Pharm. 282 (2004) 73-85
21. Neau S.H., and Flynn G.L. Solid and liquid heat capacity of n-alkyl para-aminobenzoate near the melting point. Pharm. Res. 11 (1990) 1157-1162
22. Niea Q., and Wang J.K. Solubility of 16,17-epoxyprogesterone in six different solvents. J. Chem. Eng. Data 50 (2005) 1750-1752
23. Niea Q., Wang J.K., and Yina Q. Separation and purification of two isomorphic steroids by a novel extractive drowning out crystallization. Sep. Purif. Technol. 50 (2006) 342-346
24. Palinski W. Immunomodulation: a new role for statins. Nat. Med. 6 (2000) 1311-1312
25. Prausnitz J.M., Lichtenthaler R.N., and Gomes de Azevedo E. Molecular Thermodynamics of Fluid-phase Equilibria. second ed. (1986), Prentice-Hall, Englewood Cliffs, NJ
26. Ren G.B., and Wang J.K. Solubility of dl-p-hydroxyphenylglycine sulfate in binary acetone + water solvent mixtures. J. Chem. Eng. Data 49 (2004) 1376-1378
27. Ren G.B., Wang J.K., Yin Q.X., and Zhang M.J. Solubilities of proxetine hydrochloride hemihydrate between 286 K and 363 K. J. Chem. Eng. Data 49 (2004) 1671-1674
28. Roberts K.L., Rousseau R.W., and Teja A.S. Solubility of long-chain n-alkanes in heptane between 280 and 350 K. J. Chem. Eng. Data 39 (1994) 793-795
29. Rubino J.T., and Obeng E.K. Influence of solute structure on deviations from the log-linear solubility equation in propylene-glycol: water mixtures. J. Pharm. Sci. 80 (1991) 479-483
30. Ruckenstein E., and Shulgin I. The solubility of solids in mixtures composed of a supercritical fluid and an entrainer. Fluid Phase Equilib. 200 (2002) 53-67
31. Ruckenstein E., and Shulgin I. Solubility of drugs in aqueous solutions. Part 1. Ideal mixed solvent approximation. Int. J. Pharm. 258 (2003) 193-201
32. Ruckenstein E., and Shulgin I. Solubility of drugs in aqueous solutions Part 4. Drug solubility by the dilute approximation. Int. J. Pharm. 278 (2004) 221-229
33. Shachter M. Chemical, pharmacokinetic and pharmacodynamic properties of statins: an update. Fundam. Clin. Pharmacol. 19 (2004) 117-125
34. Souza M., Conceição M., Silva M., Soledade L., and Souza L.A. Thermal and kinetic study of statins. J. Therm. Anal. Calorim. 87 (2007) 859-863
35. Strode J.T.B., Taylor L.T., Howard A.L., and Ip D. Feasibility of lovastatin analysis by packed column supercritical fluid chromatography with ultraviolet detection. J. Pharm. Biomed. Anal. 20 (1999) 137-143
36. Sun H., Gong J., and Wang J.K. Solubility of lovastatin in acetone, methanol, ethanol, ethyl acetate, and butyl acetate between 283 K and 323 K. J. Chem. Eng. Data 50 (2005) 1389-1391
37. Sutherland A., Auclair K., and Vederas J.C. Recent advances in the biosynthetic studies of lovastatin. Curr. Opin. Drug Discov. Dev. 4 (2003) 229-236
38. Tiziana F., Montanes F., Olano A., and Ibanez E. Modeling solubilities of sugars in alcohols based on original experimental data. J. AIChE 53 (2007) 2411-2418
39. Vincenzi B., Santini D., Avvisati G., Baldi A., La Cesa A., and Tonini G. Statins may potentiate bisphosphonates anticancer properties: a new pharmacological approach. Med. Hypotheses 61 (2003) 98-101
40. Wang S., Wang J.K., and Yin Q.X. Measurement and correlation of solubility of 7-aminocephalosporanic acid in aqueous acetone mixtures. Ind. Eng. Chem. Res. 44 (2005) 3783-3787