The effect of ionized species on microsomal binding

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 202-205

  Abraham, Michael H ^a   Austin, Rupert P ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b BioCity   (United Kingdom)

Author keywords

Carboxylate anions; Linear free energy relationship; Microsomal binding; Microsomal binding of ions; Protonated base cations

Indexed keywords

ALBENDAZOLE; ALIMEMAZINE; ALPRAZOLAM; AMIODARONE; ANION; ASTEMIZOLE; BASE; BETAXOLOL; CARBAMAZEPINE; CARBOXYLIC ACID; CATION; CERIVASTATIN; CLOMIPRAMINE; CLOZAPINE; GLIBENCLAMIDE; INDOMETACIN; ISRADIPINE; MEBENDAZOLE; METHOCARBAMOL; OXAPROZIN; PHENSUXIMIDE; PHOSPHATE; PHOSPHOLIPID; PIMOZIDE; PROMETHAZINE; PROPAFENONE; SULINDAC; TAMOXIFEN; THIORIDAZINE; UNINDEXED DRUG;

ACIDITY; ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; DRUG BINDING; HYDROGEN BOND; IONIZATION; LINEAR FREE ENERGY RELATIONSHIP; MICROSOME; MOLECULAR INTERACTION; PROTON TRANSPORT;

CARBOXYLIC ACIDS; IONS; MICROSOMES; PROTONS;

EID: 84855793683     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.043     Document Type: Article

References (21)

1. R.S. Obach The importance of nonspecific binding in in vitro matrices, its impact on enzyme kinetic studies of drug metabolism and implications for in vitro-in vivo correlations Drug Metab. Dispos. 24 1996 1047 1049
2. H. Gao, S.J. Steyn, G. Chang, and J. Lin Assessment of in silico models for fraction of unbound drug in human liver microsomes Expert Opin. Drug Metab. Toxicol. 6 5 2010 533 542
3. R.P. Austin, P. Barton, S.L. Cockroft, M.C. Wenlock, and R.J. Riley The influence of nonspecific microsomal binding on apparent intrinsic clearance, and its prediction from physicochemical properties Drug Metab. Dispos. 30 2002 1497 1503
4. D. Hallifax, and J.B. Houston Binding of drugs to hepatic microsomes: comment and assessment of current prediction methodology with recommendation for improvement Drug Metab. Dispos. 34 2006 724 726
5. H. Gao, L. Yao, H.W. Mathieu, Y. Zhang, T.S. Maurer, M.D. Troutman, D.O. Scott, R.B. Ruggeri, and J. Lin In silico modeling of nonspecific binding to human liver microsomes Drug Metab. Dispos. 36 2008 2130 2135
6. R.S. Obach Nonspecific binding to microsomes: impact on scale-up of in vitro intrinsic clearance to hepatic clearance as assessed through examination of warfarin, imipramine and propranolol Drug Metab. Dispos. 25 1997 1359 1369
7. R.S. Obach Prediction of human clearance of twenty nine drugs from hepatic microsomal clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes Drug Metab. Dispos. 27 1999 1350 1359
8. R.P. Austin, A.M. Davis, and C.N. Manners Partitioning of ionizing molecules between aqueous buffers and phospholipid vesicles J. Pharm. Sci. 84 1995 1180 1183
9. S.D. Kramer, A. Braun, C. Jakits-Deiser, and H. Wunderli-Allenspach Towards the predictability of drug-lipid membrane interactions: the pH-dependent affinity of propranolol to phosphatidylinositol containing liposomes Pharm. Res. 15 1998 739 744
10. M.H. Abraham, R.E. Smith, R. Luchtefeld, A.J. Boorem, R. Luo, and W.E. Acree Jr. Prediction of solubility of drugs and other compounds in organic solvents J. Pharm. Sci. 99 2010 1500 1515
11. Y.H. Zhao, J. Le, M.H. Abraham, A. Hersey, P.E. Eddershaw, C.N. Luscombe, D. Butina, G. Beck, B. Sherborne, I. Cooper, and J.A. Platts Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors J. Pharm. Sci. 90 2001 749 784
12. M.H. Abraham, and F. Martins Human skin permeation and partition; general Linear Free-Energy Relationship analyses J. Pharm. Sci. 93 2004 1508 1523
13. M.H. Abraham, A. Ibrahim, Y. Zhao, and W.E. Acree Jr. A data base for partition of volatile organic compounds and drugs from blood/plasma/serum to brain, and an LFER analysis of the data J. Pharm. Sci. 95 2006 2091 2100
14. M.H. Abraham The permeation of neutral molecules, ions and ionic species through membranes: brain permeation as an example J. Pharm. Sci. 100 2011 1690 1701
15. M.H. Abraham Chem. Soc. Rev. 22 1993 73 83
16. M.H. Abraham, A. Ibrahim, and A.M. Zissimos J. Chromatogr. A 1037 2004 29 47
17. M.H. Abraham, and W.E. Acree Jr. Equations for the transfer of neutral molecules and ionic species from water to organic phases J. Org. Chem. 75 2010 1006 1015
18. M.H. Abraham, and W.E. Acree Jr. Solute descriptors for phenoxide anions and their use to establish correlations of rates of reaction of anions with iodomethane J. Org. Chem. 75 2010 3021 3026
19. M.H. Abraham, and W.E. Acree Jr. The transfer of neutral molecules, ions and ionic species from water to ethylene glycol and to propylene carbonate; descriptors for pyridinium cations New J. Chem. 34 2010 2298 2305
20. M.H. Abraham, and W.E. Acree Jr. The transfer of neutral molecules, ions and ionic species from water to wet octanol Phys. Chem. Chem. Phys. 12 2010 13182 13188
21. K. Zhang, M. Chen, G.K.E. Scriba, M.H. Abraham, A. Fahr, and X. Lui Linear free energy analysis of retention factors in cerasome electrokinetic chromatography intended for predicting skin permeation J. Pharm. Sci. 100 2011 3105 3113