The solution properties of mefenamic acid and a closely related analogue are indistinguishable in polar solvents but significantly different in nonpolar environments

Journal of Pharmaceutical Sciences

Volumn 101, Issue 12, 2012, Pages 4529-4539

  Lee, Eun Hee ^a,b   Byrn, Stephen R ^a   Pinal, Rodolfo ^a  

^a PURDUE UNIVERSITY   (United States)

^b Korea University   (South Korea)

Author keywords

Activity coefficients; Chemical analogues; Complexation; Cosolute effect; Flufenamic acid; Mefenamic acid; Solubility; Solubilization; Solubilization model; Thermodynamic activity

Indexed keywords

EID: 84868204467     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23316     Document Type: Article

References (11)

1. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. 1997. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 23:3-25.
2. Mukuta T, Lee AY, Kawakami T, Myerson AS. 2005. Influence of impurities on the solution-mediated phase transformation of an active pharmaceutical ingredient. Cryst Growth Des 5:1429-1436.
3. Aguiar AJ, Zelmer JE. 1969. Dissolution behavior of polymorphs of chloramphenicol palmitate and mefenamic acid. J Pharm Sci 58:983-987.
4. Burger A, Ramberger R. 1980. Thermodynamic relationships between polymorphic modifications. Flufenamic acid and mefenamic acid. Mikrochim Acta 1:17-28.
5. Mao C, Pinal R, Morris KR. 2005. A quantitative model to evaluate solubility relationship of polymorphs from their thermal properties. Pharm Res 22:1149-1157.
6. Cline PV, Delfino JJ, Rao PSC. 1991. Partitioning of aromatic constituents into water from gasoline and other complex solvent mixtures. Environ Sci Technol 25:914-920.
7. Grant DJW, Higuchi T. 1990. Solubility behavior of organic compounds. New York : Wiley-Interscience.
8. Pinal R, Lee LS, Rao PSC. 1991. Prediction of the solubility of hydrophobic compounds in nonideal solvent mixtures. Chemosphere 22:939-951.
9. TishmackPA, BugayDE, ByrnSR 2003. Solid-stateNuclearMagneticResonancespectroscopy-pharmaceuticalapplications. J Pharm Sci 92:441-474.
10. Snyder LR. 1978. Classification of solvent properties of common liquids. J Chromatogr Sci 16:223-234.
11. Nehm SJ, Rodriguez-Spong B, Rodriguez-Hornedo N. 2006. Phase solubility diagrams of cocrystals are explained by solubility product and solution complexation. Cryst Growth Des 6:592-600.