A hybrid approach to advancing quantitative prediction of tissue distribution of basic drugs in human.

A general toxicity of basic drugs is related to phospholipidosis in tissues. Therefore, it is essential to predict the tissue distribution of basic drugs to facilitate an initial estimate of that toxicity. The objective of the present study was to further assess the original prediction method that consisted of using the binding to red blood cells measured in vitro for the unbound drug (RBCu) as a surrogate for tissue distribution, by correlating it to unbound tissue:plasma partition coefficients (Kpu) of several tissues, and finally to predict volume of distribution at steady-state (V(ss)) in humans under in vivo conditions. This correlation method demonstrated inaccurate predictions of V(ss) for particular basic drugs that did not follow the original correlation principle. Therefore, the novelty of this study is to provide clarity on the actual hypotheses to identify i) the impact of pharmacological mode of action on the generic correlation of RBCu-Kpu, ii) additional mechanisms of tissue distribution for the outlier drugs, iii) molecular features and properties that differentiate compounds as outliers in the original correlation analysis in order to facilitate its applicability domain alongside the properties already used so far, and finally iv) to present a novel and refined correlation method that is superior to what has been previously published for the prediction of human V(ss) of basic drugs. Applying a refined correlation method after identifying outliers would facilitate the prediction of more accurate distribution parameters as key inputs used in physiologically based pharmacokinetic (PBPK) and phospholipidosis models.

[1]  N. Dzimiri,et al.  Class I antiarrhythmic drug effects on ouabain binding to guinea pig cardiac Na+ -K+ ATPase. , 1999, Canadian journal of physiology and pharmacology.

[2]  M. Gassmann,et al.  Functional NMDA receptors in rat erythrocytes. , 2010, American journal of physiology. Cell physiology.

[3]  L. Neyses,et al.  Human red blood cells--an ideal model system for the action of calcium agonists and antagonists. , 1984, Journal of hypertension. Supplement : official journal of the International Society of Hypertension.

[4]  S. Kathöfer,et al.  Antiarrhythmic drug carvedilol inhibits HERG potassium channels. , 2001, Cardiovascular research.

[5]  K. Gingrich,et al.  Ketamine Blockade of Voltage-gated Sodium Channels: Evidence for a Shared Receptor Site with Local Anesthetics , 2001, Anesthesiology.

[6]  E. Bertaccini,et al.  Molecular modelling of specific and non-specific anaesthetic interactions. , 2002, British journal of anaesthesia.

[7]  J. Nezu,et al.  Molecular and Physiological Evidence for Multifunctionality of Carnitine / Organic Cation Transporter OCTN 2 , 2001 .

[8]  A. Grabinsky Mechanisms of neural blockade. , 2005, Pain physician.

[9]  Ovidiu Daescu,et al.  The Human Red Blood Cell Proteome and Interactome , 2007, Experimental biology and medicine.

[10]  M. Suwalsky,et al.  Effects of the local anesthetic benzocaine on the human erythrocyte membrane and molecular models. , 2004, Biophysical chemistry.

[11]  K. Venkataraman,et al.  Effects of diltiazem on cation transport across erythrocyte membranes of hypertensive humans. , 1987, Hypertension.

[12]  P. Romero,et al.  Voltage-dependent calcium channels in young and old human red cells , 2007, Cell Biochemistry and Biophysics.

[13]  Anthony E. Klon,et al.  Improved Naïve Bayesian Modeling of Numerical Data for Absorption, Distribution, Metabolism and Excretion (ADME) Property Prediction , 2006, J. Chem. Inf. Model..

[14]  T. Akata General Anesthetics and Vascular Smooth Muscle: Direct Actions of General Anesthetics on Cellular Mechanisms Regulating Vascular Tone , 2007, Anesthesiology.

[15]  K. Hanada,et al.  Enantioselective Tissue Distribution of the Basic Drugs Disopyramide, Flecainide and Verapamil in Rats: Role of Plasma Protein and Tissue Phosphatidylserine Binding , 1998, Pharmaceutical Research.

[16]  D. Tosteson,et al.  Voltage-activated cation transport in human erythrocytes. , 1989, The American journal of physiology.

[17]  J. Corradi,et al.  Phospholipidosis as a function of basicity, lipophilicity, and volume of distribution of compounds. , 2010, Chemical research in toxicology.

[18]  Patrick Poulin,et al.  Prediction of pharmacokinetics prior to in vivo studies. 1. Mechanism-based prediction of volume of distribution. , 2002, Journal of pharmaceutical sciences.

[19]  M. Rowland,et al.  Physiologically based pharmacokinetic modeling 1: predicting the tissue distribution of moderate-to-strong bases. , 2005, Journal of pharmaceutical sciences.

[20]  L. Berezhkovskiy,et al.  Volume of distribution at steady state for a linear pharmacokinetic system with peripheral elimination. , 2004, Journal of pharmaceutical sciences.

[21]  T. Arakawa,et al.  Optimization of Lyophilization Conditions for Recombinant Human Interleukin-2 by Dried-State Conformational Analysis Using Fourier-Transform Infrared Spectroscopy , 1995, Pharmaceutical Research.

[22]  Philip Prathipati,et al.  Global Bayesian Models for the Prioritization of Antitubercular Agents , 2008, J. Chem. Inf. Model..

[23]  S. Aizawa,et al.  Expression of organic cation transporter OCTN1 in hematopoietic cells during erythroid differentiation. , 2004, Experimental hematology.

[24]  M. Blaustein,et al.  Phencyclidine in low doses selectively blocks a presynaptic voltage-regulated potassium channel in rat brain. , 1986, Proceedings of the National Academy of Sciences of the United States of America.

[25]  K. Gingrich,et al.  Meperidine and lidocaine block of recombinant voltage-dependent Na+ channels: evidence that meperidine is a local anesthetic. , 1999, Anesthesiology.

[26]  R. Henriksson,et al.  Ondansetron but not granisetron affect cell volume regulation and potassium ion transport of glioma cells treated with estramustine phosphate , 2002, Journal of Cancer Research and Clinical Oncology.

[27]  Sean Ekins,et al.  Novel Inhibitors of Human Organic Cation/Carnitine Transporter (hOCTN2) via Computational Modeling and In Vitro Testing , 2009, Pharmaceutical Research.

[28]  M. Suwalsky,et al.  Structural effects of the local anesthetic bupivacaine hydrochloride on the human erythrocyte membrane and molecular models. , 2002, Blood cells, molecules & diseases.

[29]  H. Kutchai,et al.  Effects of local anaesthetics on the activity of the Na,K-ATPase of canine renal medulla. , 1999, Pharmacological research.

[30]  M. Omata,et al.  Inhibitory effects of carvedilol on calcium channels in vascular smooth muscle cells. , 2003, Japanese Heart Journal.

[31]  Jhi-Joung Wang,et al.  Class I antiarrhythmic drugs produced a spinal anesthetic effect in rats , 2011, Neuroscience Letters.

[32]  Cell chemistry and physiology , 1995 .

[33]  I. Ozmen,et al.  Effects of antiemetic drugs on glucose 6-phosphate dehydrogenase and some antioxidant enzymes. , 2004, Pharmacological research.

[34]  H. Fozzard,et al.  Molecular Modeling of Local Anesthetic Drug Binding by Voltage-Gated Sodium Channels , 2005, Molecular Pharmacology.

[35]  Hondeghem Lm,et al.  Quantitative structure activity studies of antiarrhythmic properties in a series of lidocaine and procainamide derivatives. , 1988, The Journal of pharmacology and experimental therapeutics.

[36]  D. Rogers,et al.  Using Extended-Connectivity Fingerprints with Laplacian-Modified Bayesian Analysis in High-Throughput Screening Follow-Up , 2005, Journal of biomolecular screening.

[37]  J. H. Ye,et al.  Ondansetron Exhibits the Properties of a Local Anesthetic , 1997, Anesthesia and analgesia.

[38]  M. Chiba,et al.  Pharmacokinetic correlation between in vitro hepatic microsomal enzyme kinetics and in vivo metabolism of imipramine and desipramine in rats. , 1990, Journal of pharmaceutical sciences.

[39]  Patrick Poulin,et al.  Development of a novel method for predicting human volume of distribution at steady-state of basic drugs and comparative assessment with existing methods. , 2009, Journal of pharmaceutical sciences.

[40]  Franco Lombardo,et al.  Prediction of volume of distribution values in humans for neutral and basic drugs using physicochemical measurements and plasma protein binding data. , 2002, Journal of medicinal chemistry.

[41]  Malcolm Rowland,et al.  Mechanistic Approaches to Volume of Distribution Predictions: Understanding the Processes , 2007, Pharmaceutical Research.

[42]  Franco Lombardo,et al.  Prediction of human volume of distribution values for neutral and basic drugs. 2. Extended data set and leave-class-out statistics. , 2004, Journal of medicinal chemistry.

[43]  E. Nishiguchi,et al.  Lidocaine action and conformational changes in cytoskeletal protein network in human red blood cells. , 1995, European journal of pharmacology.

[44]  P. Low,et al.  Anesthetic-ion channel interactions: the effect of lidocaine on the stability and transport properties of the membrane-spanning domain of band 3. , 1982, Archives of biochemistry and biophysics.

[45]  T. Murakami,et al.  Phosphatidylserine as a Determinant for the Tissue Distribution of Weakly Basic Drugs in Rats , 1990, Pharmaceutical Research.

[46]  J. Nezu,et al.  Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. , 2001, Molecular pharmacology.

[47]  David Rogers,et al.  Cheminformatics analysis and learning in a data pipelining environment , 2006, Molecular Diversity.

[48]  A. Becchetti,et al.  New Trends in Cancer Therapy: Targeting Ion Channels and Transporters , 2010, Pharmaceuticals.

[49]  N. Hamasaki,et al.  Mechanism of the change in shape of human erythrocytes induced by lidocaine. , 1995, Cell structure and function.

[50]  M. Annetta,et al.  Ketamine: new indications for an old drug. , 2005, Current drug targets.

[51]  P. Hinderling,et al.  Red blood cells: a neglected compartment in pharmacokinetics and pharmacodynamics. , 1997, Pharmacological reviews.

[52]  Sean Ekins,et al.  Shape signatures: new descriptors for predicting cardiotoxicity in silico. , 2008, Chemical research in toxicology.

[53]  A. Gere,et al.  Tolperisone-Type Drugs Inhibit Spinal Reflexes via Blockade of Voltage-Gated Sodium and Calcium Channels , 2005, Journal of Pharmacology and Experimental Therapeutics.

[54]  T. Kleyman,et al.  Brief report: trimethoprim-induced hyperkalemia in a patient with AIDS. , 1993, The New England journal of medicine.

[55]  T. Morita,et al.  Effects of diltiazem on the physicochemical properties of rat erythrocyte and liposome membrane: comparison with pentoxifylline and propranolol. , 1984, Japanese journal of pharmacology.

[56]  A. Bender,et al.  Analysis of Pharmacology Data and the Prediction of Adverse Drug Reactions and Off‐Target Effects from Chemical Structure , 2007, ChemMedChem.

[57]  R. Chicheportiche,et al.  Anaesthetic properties of phencyclidine (PCP) and analogues may be related to their interaction with Na+ channels. , 1989, European journal of pharmacology.

[58]  Gregory W. Kauffman,et al.  Physicochemical Features of the hERG Channel Drug Binding Site* , 2004, Journal of Biological Chemistry.

[59]  Y. Deyama,et al.  Inhibition mechanism of Na, K-ATPase activity by local anesthetics and its reversibility , 1999 .

[60]  Sean Ekins,et al.  Integrated in silico-in vitro strategy for addressing cytochrome P450 3A4 time-dependent inhibition. , 2010, Chemical research in toxicology.

[61]  L. Bulla,et al.  The Human Erythrocyte Proteome , 2004, Molecular & Cellular Proteomics.

[62]  H. Fozzard,et al.  Using Lidocaine and Benzocaine to Link Sodium Channel Molecular Conformations to State-Dependent Antiarrhythmic Drug Affinity , 2009, Circulation research.