Chemometrics as a valuable tool for evaluating interactions between antiretroviral drugs and food

Clinically significant interactions with food occur for more than half of antiretroviral drugs. Different physiochemical properties deriving from the chemical structures of antiretroviral drugs may contribute to the variable food effect. Chemometric methods allow analysing a large number of interrelated variables concomitantly and visualizing correlations between them. We used a chemometric approach to determine the types of correlations among different features of antiretroviral drugs and food that may influence interactions.

[1]  P. Paśko,et al.  Interactions of Antiretroviral Drugs with Food, Beverages, Dietary Supplements, and Alcohol: A Systematic Review and Meta-analyses , 2022, AIDS and Behavior.

[2]  J. Hładyszowski,et al.  From the Electron Density Gradient to the Quantitative Reactivity Indicators: Local Softness and the Fukui Function , 2022, ACS omega.

[3]  Shu Dong,et al.  Bioequivalence Evaluation of Two Formulations of Tenofovir Alafenamide Tablets in Healthy Subjects Under Fasting and Fed Conditions , 2021, Drug design, development and therapy.

[4]  E. Dumont,et al.  A Phase 1 Study to Assess the Relative Bioavailability, Food Effect, and Safety of a Tablet Formulation of GSK2838232, a Novel HIV Maturation Inhibitor in Healthy Participants After Single and Repeated Doses , 2020, Clinical pharmacology in drug development.

[5]  B. Wynne,et al.  The Effect of Moderate- and High-Fat Meals on the Bioavailability of Dolutegravir/Rilpivirine Fixed-Dose Combination Tablet , 2020, Clinical pharmacology : advances and applications.

[6]  Yusra Sajid Kiani,et al.  Lipophilic Metabolic Efficiency (LipMetE) and Drug Efficiency Indices to Explore the Metabolic Properties of the Substrates of Selected Cytochrome P450 Isoforms , 2019, ACS omega.

[7]  Machiko Watanabe,et al.  Relationship between the effects of food on the pharmacokinetics of oral antineoplastic drugs and their physicochemical properties , 2019, Journal of Pharmaceutical Health Care and Sciences.

[8]  Christopher Southan,et al.  THE CONCISE GUIDE TO PHARMACOLOGY 2019/20: Enzymes , 2019, British journal of pharmacology.

[9]  G. Bloomfield,et al.  Characteristics, Prevention, and Management of Cardiovascular Disease in People Living With HIV: A Scientific Statement From the American Heart Association. , 2019, Circulation.

[10]  Murali M. Yallapu,et al.  Pharmacokinetics and pharmacodynamics of cytochrome P450 inhibitors for HIV treatment , 2019, Expert opinion on drug metabolism & toxicology.

[11]  J. Sikora,et al.  Animals in Iodine Deficiency or Sulfadimethoxine Models of Thyroid Damage Are Differently Affected by the Consumption of Brassica Sprouts , 2019, Biological Trace Element Research.

[12]  P. Lacor,et al.  Current challenges in the treatment of HIV. , 2018, Polish archives of internal medicine.

[13]  W. Spreen,et al.  Effect of a High‐Fat Meal on the Pharmacokinetics of the HIV Integrase Inhibitor Cabotegravir , 2018, Clinical pharmacology in drug development.

[14]  M. Murray,et al.  A Review of Long-Term Toxicity of Antiretroviral Treatment Regimens and Implications for an Aging Population , 2018, Infectious Diseases and Therapy.

[15]  A. Willig,et al.  Practice Paper of the Academy of Nutrition and Dietetics: Nutrition Intervention and Human Immunodeficiency Virus Infection. , 2018, Journal of the Academy of Nutrition and Dietetics.

[16]  M. Rizk,et al.  Single‐ and Multiple‐Dose Pharmacokinetics of Once‐Daily Formulations of Raltegravir , 2018, Clinical pharmacology in drug development.

[17]  Romà Tauler,et al.  Chemometrics in analytical chemistry—part I: history, experimental design and data analysis tools , 2017, Analytical and Bioanalytical Chemistry.

[18]  A. Calcagno,et al.  Genetic Polymorphisms Affecting the Pharmacokinetics of Antiretroviral Drugs , 2017, Clinical Pharmacokinetics.

[19]  K. Yee,et al.  The Effect of Food on Doravirine Bioavailability: Results from Two Pharmacokinetic Studies in Healthy Subjects , 2017, Clinical Drug Investigation.

[20]  Olivier Michielin,et al.  SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules , 2017, Scientific Reports.

[21]  N. Ford,et al.  Patient-Reported Barriers to Adherence to Antiretroviral Therapy: A Systematic Review and Meta-Analysis , 2016, PLoS medicine.

[22]  E. Overton,et al.  Metabolic Complications and Glucose Metabolism in HIV Infection: A Review of the Evidence , 2016, Current HIV/AIDS Reports.

[23]  J. Troya,et al.  Safety and Tolerability: Current Challenges to Antiretroviral Therapy for the Long-Term Management of HIV Infection. , 2016, AIDS reviews.

[24]  P. Zagrodzki,et al.  Chemometric analysis of the interactions among different parameters describing health conditions, breast cancer risk and fatty acids profile in serum of rats supplemented with conjugated linoleic acids. , 2016, Prostaglandins, leukotrienes, and essential fatty acids.

[25]  M. Grimm,et al.  Investigation of pH and Temperature Profiles in the GI Tract of Fasted Human Subjects Using the Intellicap(®) System. , 2015, Journal of pharmaceutical sciences.

[26]  S. Piscitelli,et al.  Bioequivalence of a Dolutegravir, Abacavir, and Lamivudine Fixed-Dose Combination Tablet and the Effect of Food , 2014, Journal of acquired immune deficiency syndromes.

[27]  S. Irie,et al.  Effects of a protein-rich drink or a standard meal on the pharmacokinetics of elvitegravir, cobicistat, emtricitabine and tenofovir in healthy Japanese male subjects: A randomized, three-way crossover study , 2014, Journal of clinical pharmacology.

[28]  David K. Henderson,et al.  Updated US Public Health Service Guidelines for the Management of Occupational Exposures to Human Immunodeficiency Virus and Recommendations for Postexposure Prophylaxis , 2013, Infection Control & Hospital Epidemiology.

[29]  H. Crauwels,et al.  Impact of Food and Different Meal Types on the Pharmacokinetics of Rilpivirine , 2013, Journal of clinical pharmacology.

[30]  A. McDonnell,et al.  Basic Review of the Cytochrome P450 System , 2013, Journal of the advanced practitioner in oncology.

[31]  L. Kosmiski.  Energy expenditure in HIV infection. , 2011, The American journal of clinical nutrition.

[32]  M. Caglayan,et al.  Optimisation and validation of liquid chromatographic and partial least-squares-1 methods for simultaneous determination of enalapril maleate and nitrendipine in pharmaceutical preparations , 2011 .

[33]  W. Haefeli,et al.  Long‐Term Efavirenz Autoinduction and Its Effect on Plasma Exposure in HIV Patients , 2010, Clinical pharmacology and therapeutics.

[34]  Yuko Ito,et al.  Human CYPs involved in drug metabolism: structures, substrates and binding affinities , 2010, Expert opinion on drug metabolism & toxicology.

[35]  V. Vyncke,et al.  Effects of Different Meal Compositions and Fasted State on the Oral Bioavailability of Etravirine , 2008, Pharmacotherapy.

[36]  Pieterjan Lenain,et al.  Interplay between hydrogen bond formation and multicenter pi-electron delocalization: intermolecular hydrogen bonds. , 2008, The journal of physical chemistry. A.

[37]  J. Lundgren,et al.  European AIDS Clinical Society (EACS) guidelines on the prevention and management of metabolic diseases in HIV * , 2008, HIV medicine.

[38]  J. Tack,et al.  Parallel Monitoring of Plasma and Intraluminal Drug Concentrations in Man After Oral Administration of Fosamprenavir in the Fasted and Fed State , 2007, Pharmaceutical Research.

[39]  R. Hoetelmans,et al.  The Effect of Different Meal Types on the Pharmacokinetics of Darunavir (TMC114)/Ritonavir in HIV‐Negative Healthy Volunteers , 2007, Journal of clinical pharmacology.

[40]  Nikita Basant,et al.  Multi-way partial least squares modeling of water quality data. , 2007, Analytica chimica acta.

[41]  Yi-Zeng Liang,et al.  Plasma fatty acid metabolic profiling and biomarkers of type 2 diabetes mellitus based on GC/MS and PLS‐LDA , 2006, FEBS letters.

[42]  Jooil Kim,et al.  Food-Effect Bioavailability and Fed Bioequivalence Studies , 2005 .

[43]  Ralph G. Pearson,et al.  Chemical hardness and density functional theory , 2005 .

[44]  K. Blennow,et al.  Proteomics for drug target discovery , 2004 .

[45]  E. O'Mara,et al.  Effect of Food on the Oral Bioavailability of Didanosine from Encapsulated Enteric‐Coated Beads , 2002, Journal of clinical pharmacology.

[46]  J. Hermens,et al.  Aqueous Solubility−Molecular Size Relationships: A Mechanistic Case Study Using C10- to C19-Alkanes , 2002 .

[47]  D. Cooper,et al.  HIV‐associated lipodystrophy , 2001, HIV medicine.

[48]  Jacek Korchowiec,et al.  Recognition of the Electrophilic and Nucleophilic Centers in Molecules Via the Radical Charge Transfer Fukui Function , 2000, Comput. Chem..

[49]  W. Prince,et al.  Abacavir: Absolute Bioavailability, Bioequivalence of Three Oral Formulations, and Effect of Food , 1999, Pharmacotherapy.

[50]  G. E. Pakes,et al.  Lamivudine/Zidovudine as a Combined Formulation Tablet: Bioequivalence Compared with Lamivudine and Zidovudine Administered Concurrently and the Effect of Food on Absorption , 1999, Journal of clinical pharmacology.

[51]  B. Wills,et al.  Introduction to Principal Components Analysis , 1999, astro-ph/9905079.

[52]  D. Fleisher,et al.  Meal Composition Effects on the Oral Bioavailability of Indinavir in HIV-Infected Patients , 1999, Pharmaceutical Research.

[53]  J. Korchowiec,et al.  THE CHARGE TRANSFER FUKUI FUNCTION : EXTENSION OF THE FINITE-DIFFERENCE APPROACH TO REACTIVE SYSTEMS , 1998 .

[54]  S. Kaul,et al.  Effect of Food on the Bioavailability of Stavudine in Subjects with Human Immunodeficiency Virus Infection , 1998, Antimicrobial Agents and Chemotherapy.

[55]  G. McClelland,et al.  The Use of Pharmacoscintigraphy to Elucidate Food Effects Observed with a Novel Protease Inhibitor (Saquinavir) , 1998, Pharmaceutical Research.

[56]  B. Bannwarth,et al.  Relationship between lipophilicity and binding to human serum albumin of arylpropionic acid non-steroidal anti-inflammatory drugs. , 1997, Journal of pharmaceutical and biomedical analysis.

[57]  S. Passe,et al.  The Effect of Food on Pharmacokinetics of Zalcitabine in HIV-Positive Patients , 1995, Pharmaceutical Research.

[58]  A. Lázníčková,et al.  The effect of lipophilicity on the protein binding and blood cell uptake of some acidic drugs. , 1995, Journal of pharmaceutical and biomedical analysis.

[59]  Tapan K. Ghanty,et al.  Correlation between hardness, polarizability, and size of atoms, molecules, and clusters , 1993 .

[60]  J. Korchowiec,et al.  Group electronegativity and Fukui function studies of the substituent effects in aromatic and inorganic systems , 1992 .

[61]  Bruce R. Kowalski,et al.  Prediction of Product Quality from Spectral Data Using the Partial Least-Squares Method , 1984 .

[62]  A. D'anna.  [Interactions between drugs and food]. , 1973, Minerva medica.

[63]  G. Bloomfield,et al.  AHA SCIENTIFIC STATEMENT Characteristics , Prevention , and Management of Cardiovascular Disease in People Living With HIV A Scientific Statement From the American Heart Association Circulation , 2019 .

[64]  H. Kovari,et al.  Characteristics , Prevention , and Management of Cardiovascular Disease in People Living With HIV : A Scientific Statement From the American Heart Association , 2019 .

[65]  P. Paśko.  Drugs and Food Interactions: Food–Drug Interactions Among the Elderly: Risk Assessment and Recommendations for Patients , 2019, Reference Module in Biomedical Sciences.

[66]  Roberto Todeschini,et al.  Molecular Descriptors for Structure-Activity Applications: A Hands-On Approach. , 2018, Methods in molecular biology.

[67]  Diagnosis and Management of Acute HIV , 2018 .

[68]  W. Heneine,et al.  Announcement: Updated Guidelines for Antiretroviral Postexposure Prophylaxis after Sexual, Injection-Drug Use, or Other Nonoccupational Exposure to HIV - United States, 2016. , 2016, MMWR. Morbidity and mortality weekly report.

[69]  Hervé Abdi,et al.  Partial least squares methods: partial least squares correlation and partial least square regression. , 2013, Methods in molecular biology.

[70]  K. Raghavan,et al.  Predicting Effect of Food on Extent of Drug Absorption Based on Physicochemical Properties , 2007, Pharmaceutical Research.

[71]  A. Boulesteix,et al.  Partial least squares: a versatile tool for the analysis of high-dimensional genomic data , 2007, Briefings Bioinform..

[72]  T. Holdich,et al.  Pharmacokinetics of Single Oral Doses of Apricitabine, a Novel Deoxycytidine Analogue Reverse Transcriptase Inhibitor, in Healthy Volunteers , 2006, Clinical drug investigation.

[73]  M. Fischl,et al.  Effect of Food on the Steady-State Pharmacokinetics of Delavirdine in Patients with HIV Infection , 2003, Clinical drug investigation.

[74]  Y. Ozaki,et al.  Short-wave near-infrared spectroscopy of biological fluids. 1. Quantitative analysis of fat, protein, and lactose in raw milk by partial least-squares regression and band assignment. , 2001, Analytical chemistry.

[75]  T. Isaksson,et al.  Multivariate techniques in the analysis of meat quality. , 1996, Meat science.

[76]  Wellbutrin,et al.  Prescribing Information , 2015, European journal of haematology.

[77]  R. T. Sanderson.  Chemical Bonds and Bond Energy , 1976 .