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Modelling of absorption, distribution and physicochemical properties of AT1 receptor antagonists / Modelovanie absorpcie, distribúcie a fyzikálnochemických vlastnosti antagonistov AT1 receptorov


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[1] Abraham MH, Takacs-Novak K, Mitchell RC. On the partition of ampholytes: Application to blood-brain distribution. J Pharm Sci. 1997;86:310-315.10.1021/js960328jSearch in Google Scholar

[2] Alderman M, Aiyer KJ. Uric acid: role in cardiovascular disease and effects of losartan. Curr Med Res Opin. 2004;20:369-379.10.1185/030079904125002982Search in Google Scholar

[3] ATACAND label information, approved on 06/24/2011, NDA no. 020838. http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020838s033lbl.pdfSearch in Google Scholar

[4] AVAPRO the label information, approved on 01/18/2012, NDA no. 020757. http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020757s058lbl.pdfSearch in Google Scholar

[5] Balakin KV, Savchuk NP, Tetko IV. In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds: trends, problems and solutions. Curr Med Chem. 2006;13:223-241.10.2174/092986706775197917Search in Google Scholar

[6] Barone V, Cossi M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J Phys Chem A. 1998;102:1995-2001.10.1021/jp9716997Search in Google Scholar

[7] Benson SC, Iguchi R, Ho CI, Yamamoto K, Kurtz TW. Inhibition of cardiovascular cell proliferation by angiotensin receptor antagonists: are all molecules the same? J Hypertens. 2008;26:973-980.10.1097/HJH.0b013e3282f56ba5Search in Google Scholar

[8] Benson SC, Pershadsingh HA, Ho CI, et al. Identification of telmisartan as a unique angiotensin II receptor antagonist with selective PPARγ-modulating activity. Hypertension. 2004;43:993-1002.10.1161/01.HYP.0000123072.34629.57Search in Google Scholar

[9] Cagigal E, Gonzalez L, Alonso RM, Jimenez RM. pKa determination of angiotensin II receptor antagonists (ARA II) by spectrofluorimetry. J Pharm Biomed Anal. 2001;26:477-486.10.1016/S0731-7085(01)00413-7Search in Google Scholar

[10] Clark DE. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration. J Pharm Sci. 1999;88:815-821.10.1021/js980402t10430548Search in Google Scholar

[11] Cossi M, Rega N, Scalmani G, Barone V. Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comp Chem. 2003;24:669-681.10.1002/jcc.1018912666158Search in Google Scholar

[12] COZAAR label information, approved on 11/17/2011, NDA no. 020386. http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020386Orig1s056Lbl_REPLACEMENT.pdfSearch in Google Scholar

[13] DIOVAN label information, approved on 02/28/2012, NDA no. 021283. http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021283s035lbl.pdfSearch in Google Scholar

[14] Erbe DV, Gartrell K, Zhang YL, et al. Molecular activation of PPARγ by angiotensin II type 1-receptor antagonists. Vascul Pharmacol. 2006;45:154-162.10.1016/j.vph.2006.05.00216765099Search in Google Scholar

[15] Ertl P, Rohde B, Selzer P. Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem. 2000;43:3714-3717.10.1021/jm000942eSearch in Google Scholar

[16] Ertl P, Selzer P, Gasteiger J. Web-based calculation of molecular properties. Handbook of Chemoinformatics: From Data to Knowledge. Weinheim: Wiley-VCH; 2003, 1336-1348.Search in Google Scholar

[17] Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian, Inc., Wallingford CT, 2009.Search in Google Scholar

[18] Fukuhara M, Neves LA, Li P, Diz DI, Ferrario CM, Brosnihan KB.Search in Google Scholar

The angiotensin II AT1 receptor antagonist irbesartan prevents thromboxane A2-induced vasoconstriction in the rat hind-limb vascular bed in vivo. J Hypertens. 2001;19:561-566.10.1097/00004872-200103001-00007Search in Google Scholar

[19] Hilal S, Karickhoff SW, Carreira LA. A Rigorous Test for SPARC‘s Chemical Reactivity Models: Estimation of More Than 4300 Ionization pKa‘s. Quant Struc Act Rel. 1995;14:348-355.10.1002/qsar.19950140405Search in Google Scholar

[20] Hoieggen A, Alderman MH, Kjeldsen SE, et al. LIFE Study Group. The impact of serum uric acid on cardiovascular outcomes in the LIFE study. Kidney Int. 2004;65:1041-1049.10.1111/j.1523-1755.2004.00484.xSearch in Google Scholar

[21] http://www.syrres.comSearch in Google Scholar

[22] Inglot T, Gumieniczek A, Komsta Ł, Kasińska A. LC and Principal Component Analysis in the Lipophilicity Study of Seven Angiotensin II-AT1 Receptor Antagonists (Sartans). Chromatographia. 2008;68:977-983.10.1365/s10337-008-0801-5Search in Google Scholar

[23] Iwai M, Chen R, Imura Y, Horiuchi M. TAK-536, a new AT1 receptor blocker, improves glucose intolerance and adipocyte differentiation. Am J Hypertens. 2007;20:579-586.10.1016/j.amjhyper.2006.12.010Search in Google Scholar

[24] Je HK, Joo HL, Soo HP, Ji HK, Yong HCh. Fimasartan, a Novel Angiotensin II Receptor Antagonist. Arch Pharm Res. 2012;35:1123-1126.10.1007/s12272-012-0700-zSearch in Google Scholar

[25] Jimenez AM, Monton M, Garcia R, et al. Inhibition of platelet activation in stroke-prone spontaneously hypertensive rats: comparison of losartan, candesartan, and valsartan. J Cardiovasc Pharmacol. 2001;37:406-412.10.1097/00005344-200104000-00007Search in Google Scholar

[26] Lee SE, Kim YJ, Lee HY, et al. Efficacy and Tolerability of Fimasartan, a New Angiotensin Receptor Blocker, Compared With Losartan (50/100 mg): A 12-Week, Phase III, Multicenter, Prospective, Randomized, Double-Blind, Parallel-Group, Dose Escalation Clinical Trial With an Optional 12-Week Extension Phase in Adult Korean Patients With Mild-to-Moderate Hypertension. Clin Ther. 2012;34:552-568.10.1016/j.clinthera.2012.01.024Search in Google Scholar

[27] LexicompR (http://www.lexi.com)Search in Google Scholar

[28] Li P, Fukuhara M, Diz DI, Ferrario CM, Brosnihan KB. Novel angiotensin II AT(1) receptor antagonist irbesartan prevents thromboxane A(2)-induced vasoconstriction in canine coronary arteries and human platelet aggregation. J Pharmacol Exp Ther. 2000;292:238-246.Search in Google Scholar

[29] Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev. 1997;23:3-25.10.1016/S0169-409X(96)00423-1Search in Google Scholar

[30] Meylan WM, Howard PH. Atom/fragment contribution method for estimating octanol-water partition coefficients. J Pharm Sci. 1995;84:83-92.10.1002/jps.2600840120Search in Google Scholar

[31] MICARDIS label information, approved on 01/19/2012, NDA no. 020850. http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020850s035lbl.pdfSearch in Google Scholar

[32] MICROMEDEXR 2.0 (http://www.thomsonhc.com/micromedex2/librarian/)Search in Google Scholar

[33] Muegge I. Selection criteria for drug-like compounds. Med Res Rev. 2003;23:302-321.10.1002/med.10041Search in Google Scholar

[34] Murugesan N, Gu Z, Fadnis L, et al. Dual Angiotensin II and Endothelin A Receptor Antagonists: Synthesis of 2´-Substituted N-3-Isoxazolyl Biphenylsulfonamides with Improved Potency and Pharmacokinetics. J Med Chem. 2005;48: 171-179.10.1021/jm049548xSearch in Google Scholar

[35] Nunez A, Gomez J, Zalba LR, et al. Losartan inhibits in vitro platelet activation: comparison with candesartan and valsartan. J Renin Angio Aldo S. 2000;1:175-179.Search in Google Scholar

[36] Pardridge WM. Drug transport across the blood-brain barrier. J Cereb Blood Flow Metab. 2012;32:1959-1972.10.1038/jcbfm.2012.126Search in Google Scholar

[37] Refsgaard HHF, Jensen BF, Brockhoff PB, Padkjaer SB, Guldbrandt M, Christensen MS. In silico prediction of membrane permeability from calculated molecular parameters. J Med Chem. 2005;48:805-811.10.1021/jm049661nSearch in Google Scholar

[38] Remkova A, Kratochvilova H, Ďurina J. Impact of the therapy by renin-angiotensin system targeting antihypertensive agents perindopril versus telmisartan on prothrombotic state in essential hypertension. J Hum Hypertens. 2008;22:338-345.10.1038/sj.jhh.1002328Search in Google Scholar

[39] Sato Y, Fujii S, Imagawa S, et al. Platelet aggregability in patients with hypertension treated with angiotensin II type 1 receptor blockers. J Atheroscler Thromb. 2007;14:31-35.10.5551/jat.14.31Search in Google Scholar

[40] Schupp M, Janke J, Clasen R, Unger T, Kintscher U. Angiotensin type 1 receptor blockers induce peroxisome proliferatoractivated receptor-γ activity. Circulation. 2004;109:2054-2057.10.1161/01.CIR.0000127955.36250.65Search in Google Scholar

[41] Sica DA, Schoolwerth AC. Part 1. Uric acid and losartan. Curr Opin Nephrol Hypertens. 2002;11:475-482.10.1097/00041552-200209000-00001Search in Google Scholar

[42] Tetko IV. Computing chemistry on the web. Drug Discov Today. 2005;10:1497-1500.10.1016/S1359-6446(05)03584-1Search in Google Scholar

[43] Tetko IV, Bruneau P, Mewes HW, Rohrer DC, Poda GI. Can we estimate the accuracy of ADME-Tox predictions? Drug Discov Today. 2006;11:700-707.10.1016/j.drudis.2006.06.01316846797Search in Google Scholar

[44] Tetko IV, Gasteiger J, Todeschini R. Virtual computational chemistry laboratory--design and description. J Comput Aided Mol Des. 2005;19:453-463.10.1007/s10822-005-8694-y16231203Search in Google Scholar

[45] Tetko IV, Tanchuk VY. Application of associative neural networks for prediction of lipophilicity in ALOGPS 2.1 program. J Chem Inf Comput Sci. 2002;42:1136-1145. Search in Google Scholar

[46] Tetko IV, Tanchuk VY, Kasheva TN, Villa AEP. Estimation of aqueous solubility of chemical compounds using E-state indices. J Chem Inf Comput Sci. 2001b;41:1488-1493.10.1021/ci000392t11749573Search in Google Scholar

[47] Tetko IV, Tanchuk VY, Villa AEP. Prediction of n-octanol/water partition coefficients from PHYSPROP database using artificial neural networks and E-state indices. J Chem Inf Comput Sci. 2001a;41:1407-1421.10.1021/ci010368v11604042Search in Google Scholar

[48] Tosco P, Rolando B, Fruttero R, et al. Physicochemical Profiling of Sartans: A Detailed Study of Ionization Constants and Distribution Coefficients. Helv Chim Acta. 2008;91:468-482.10.1002/hlca.200890051Search in Google Scholar

[49] Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kapple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem. 2002;45:2615-2623.10.1021/jm020017n12036371Search in Google Scholar

[50] Wang J, Ho L, Chen L, et al. Valsartan lowers brain β-amyloid protein levels and improves spatial learning in a mouse model of Alzheimer disease. J Clin Invest. 2007;117:3393-3402.10.1172/JCI31547204031517965777Search in Google Scholar

[51] Wang RX, Fu Y, Lai LH. A New Atom-Additive Method for Calculating Partition Coefficients. J Chem Inf Comput Sci. 1997;37:615-621.10.1021/ci960169pSearch in Google Scholar

[52] Wang RX, Gao Y, Lai LH. Calculating partition coefficient by atom additive method. Perspect Drug Discov Des. 2000;19:47-66.10.1023/A:1008763405023Search in Google Scholar

[53] Wienen W., Entzeroth M, van Meel JCA, et al. A review on telmisartan: a novel long-acting angiotensin II receptor antagonist. Cardiovasc Drug Rev. 2000;18:127-156.10.1111/j.1527-3466.2000.tb00039.xSearch in Google Scholar

[54] Woo KT, Wook YB, Kwang LJ, et al. Synthesis and antihypertensive activity of pyrimidin-4(3H)-one derivatives as losartan analogue for new angiotensin II receptor type 1 (AT1) antagonists. Bioorg Med Chem Lett. 2012;22:1649-1654.10.1016/j.bmcl.2011.12.11622264484Search in Google Scholar

[55] Zhao YH, Abraham MH, Lee J, et al. Rate-limited steps of human oral absorption and QSAR studies. Pharm Res. 2002;19:1446-1457. 10.1023/A:1020444330011Search in Google Scholar

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