Abstract
Equations derived from the Clausius–Clapeyron and Prigogine–Defay equations were used to determine the free energy of mixing for diastereoisomers and enantiomers from heats of fusion and transition temperature data. These equations are applied to the thermodynamics of mixing of the six binary equimolar combinations of (lR,2S)-ephedrine, (1S,2R)-ephedrine; and (1R,2R)- and (1S,2S)-pseudo-ephedrine isomers. The relative equilibrium solubility of the binary mixtures in water is consistent with thermodynamic calculations.
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REFERENCES
I. W. Wainer, T. Doyle, J. Hamidzaheh, and J. Aldridge. J. Chromatogr. 261:123–126 (1983).
S. Barkan, J. D. Weber, and E. Smith. J. Chromatogr. 219:81–88 (1981).
P. N. Patil, J. B. LaPidus, D. Cambell, and A. Tye. J. Pharmacol. Exp. Ther. 155(1):13–23 (1967).
P. N. Patil, D. D. Miller, and U. Trendelenburg. Pharmacol. Rev. 26(4):323–392 (1974).
M. Mathew and G. J. Palenik. Acta Crystallogr. B33:1016–1022 (1977).
J. F. Malone and M. Parvez. Acta Crystallogr. A34, S76 (1978).
H. U. Pohl and H. Wollweber. Eur. J. Med. Chem. 13(2):127–139 (1978).
J. Frelek, Z. Majer, A. Perkowska, G. Snatzke, I. Vlahov, and U. Wagner. Pure Appl. Chem. 57(3):441–451 (1985).
P. S. Portoghese. J. Med. Chem. 10(6):1057–1063 (1967).
M. vanDamme, M. Hanocq, O. Denisoff, and L. Molle. Anal. Lett. 12(B4):339–349 (1979).
H.-J. Schneider and M. Lonsdorfer. Org. Magnet. Reson. 16(2):133–137 (1981).
M. Gelbcke and M. Baudet. Anal. Chim. Acta 39A(8):717–727 (1983).
C. Fouquey and J. Jacques. Bull. Soc. Chim. Fr. 165–9 (1966).
C. Fouquey and J. Jacques. Tetrahedron 23(10):4009–4019 (1967).
C. Fouquey and M. Leclercq. Tetrahedron 26(23):5637–5651 (1970).
J. Jacques, A. Collet, and S. H. Wilen. Enantiomers, Racemates, and Resolution, 1981.
R. W. Taft, M. H. Abraham, G. R. Famini, R. M. Doherty, J.-L. M. Abboud, and J. M. Kamlet. J. Pharm. Sci. 74:807–814 (1985).
M. J. Kamlet, R. M. Doherty, J.-L. M. Abboud, M. H. Abraham, and R. W. Taft. J. Pharm. Sci. 75:338–349 (1986).
G. Cave, R. Kothari, F. Puisieux, A. N. Martin, and J. T. Carstensen. Int. J. Pharm. 5(4):267–272 (1980).
G. L. Amidon and N. A. Williams. Int. J. Pharm. 11(3):249–256 (1982).
A. Beerbower, P. L. Wu, and A. Martin. J. Pharm. Sci. 73:179–194 (1984).
A. Martin and J. T. Carstensen. J. Pharm. Sci. 70(2):170–172 (1981).
Z. Liron, S. Srebrenik, A. Martin, and S. Cohen. J. Pharm. Sci. 75:463–468 (1986).
W. E. Acree, Jr. Thermodynamic Properties of Nonelectrolyte Solutions, Academic Press, London, 1984.
H. J. M. Grunbauer, A. L. J. de Meer, and H. H. van Rooij. Int. J. Pharm. 32:197 (1986).
S. H. Yalkowsky, A. A. Sinkula, and S. C. Valvani. Physical Properties of Drugs, Marcel Dekker, New York and Basel, 1982.
J. T. Rubino and S. H. Yalkowsky. Pharm. Res. 4(3):220–236 (1987).
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Schmidt, W.F., Porter, W. & Carstensen, J.T. Thermodynamics in the Prediction of the Solubilities of Binary Mixtures of the Diastereoisomers and Enantiomers of Ephedrine. Pharm Res 5, 391–395 (1988). https://doi.org/10.1023/A:1015919913896
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DOI: https://doi.org/10.1023/A:1015919913896