Influence of position and size of substituents on the mechanism of partitioning: A thermodynamic study on acetaminophens, hydroxybenzoic acids, and parabens

AAPS PharmSciTech

Volumn 9, Issue 1, 2008, Pages 205-216

  Perlovich, German L ^a,b   Volkova, Tatyana V ^b   Manin, Alex N ^b,c   Bauer Brandl, Annette ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

^b INSTITUTE OF SOLUTION CHEMISTRY   (Russian Federation)

^c IVANOVO STATE UNIVERSITY OF CHEMISTRY AND TECHNOLOGY   (Russian Federation)

Author keywords

Partitioning; Solubility; Solvation; Sublimation; Thermodynamics; Transfer

Indexed keywords

2 PARACETAMOL; 3 PARACETAMOL; 4 HYDROXYBENZOIC ACID ESTER; ACETAMIDE DERIVATIVE; HEXANE; HYDROXYBENZOIC ACID DERIVATIVE; N (2 METHYLPHENYL)ACETAMIDE; N (4 METHYLPHENYL)ACETAMIDE; OCTANOL; PARACETAMOL DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER; PARACETAMOL;

ARTICLE; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SOLUBILITY; DRUG STRUCTURE; ISOMER; MELTING POINT; SOLVATION; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; THERMODYNAMICS; VAPOR PRESSURE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; COMPUTER SIMULATION; DRUG SCREENING; EVALUATION; MOLECULAR WEIGHT;

ACETAMINOPHEN; COMPUTER SIMULATION; DRUG EVALUATION, PRECLINICAL; HYDROXYBENZOIC ACIDS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR WEIGHT; PARABENS; THERMODYNAMICS;

EID: 44849107125     PISSN: None     EISSN: 15309932     Source Type: Journal    
DOI: 10.1208/s12249-008-9033-0     Document Type: Article

References (16)

1. G. L. Perlovich, and A. Bauer-Brandl. Solvation of drugs as a key for understanding partitioning and passive transport exemplified by NSAIDs. Curr. Drug Deliv. 1: 213-226 (2004).
2. G. L. Perlovich, S. V. Rodionov, and A. Bauer-Brandl. Thermodynamics of solubility, sublimation and solvation processes of parabens. Eur. J. Pharm. Sci. 24: 25-33 (2005).
3. S. Dikstein, M. Grotto, U. Zor, M. Tamari, and F. G. Sulman. Stimulatory effect of paracetamol and its derivatives on growth and the rat tibia test. J. Endocrinol. 36: 257-262 (1966).
4. G. L. Perlovich, T. V. Volkova, and A. Bauer-Brandl. Towards an understanding of the molecular mechanism of solvation of drug molecules: a thermodynamic approach by crystal lattice energy, sublimation and solubility exemplified by paracetamol, acetanilide and phenacetin. J. Pharm. Sci. 95: 2158-2169 (2006).
5. G. L. Perlovich, T. V. Volkova, and A. Bauer-Brandl. Towards an understanding of the molecular mechanism of solvation of drug molecules: a thermodynamic approach by crystal lattice energy, sublimation and solubility exemplified by hydroxybenzoic acids. J. Pharm. Sci. 95: 1448-1458 (2006).
6. G. L. Perlovich, S. V. Kurkov, and A. Bauer-Brandl. The difference between partitioning and distribution from a thermodynamic point of view: NSAIDs as an example. Eur. J. Pharm. Sci. 27: 150-157 (2006).
7. J. D. Cox, and G. Pilcher. Thermochemistry of organic and organometallic compounds, Academic, London, UK, 1970.
8. J. S. Chickos, S. Hosseini, D. G. Hesse, and J. F. Liebman. A group additivity approach for the estimation of heat capacities of organic liquids and solids at 298 K. Struct. Chem. 4: 271-277 (1993).
9. G. A. Krestov. Thermodynamics of ionic processes in the solution, Khimiya, Leningrad, Russia, 1984, p. 271.
10. J. S. Chickos, and W. E. Acree Jr. Enthalpies of sublimation of organic and organometallic compounds 1910-2001. J. Phys. Chem. Ref. Data 31: 537-698 (1999).
11. J. L. Pascual-Ahuir, and E. Silla. GEPOL: An improved description of molecular surfaces, I: Building the spherical surface set. J. Comput. Chem. 11: 1047-1060 (1990).
12. A. I. Kitaigorodsky. The molecular crystals, Nauka, Moskva, 1971.
13. L. K. Hansen, G. L. Perlovich, and A. Bauer-Brandl. N -(3-hydroxyphenyl)acetamide. Acta Crystallogr. 62: 3627-3628 (2006).
14. G. Nichols, and C. S. Frampton. Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution. J. Pharm. Sci. 87: 684-693 (1998).
15. A. Aihara. Estimation of the energy of hydrogen bonds formed in crystals, III: Amides. Bull. Chem. Soc. Jpn. 33: 1188-1194 (1960).
16. Z. J. Li, W. H. Ojala, and D. J. W Grant. Molecular modeling study of chiral drug crystals: Lattice energy calculations. J. Pharm. Sci. 90: 1523-1539 (2001).