Physicochemical determinants of human renal clearance

Journal of Medicinal Chemistry

Volumn 52, Issue 15, 2009, Pages 4844-4852

  Varma, Manthena V S ^a   Feng, Bo ^a   Obach, R Scott ^a   Troutman, Matthew D ^a   Chupka, Jonathan ^a   Miller, Howard R ^a   El Kattan, Ayman ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; AZLOCILLIN; BETA LACTAM ANTIBIOTIC; BISOPROLOL; CARDIOVASCULAR AGENT; CHLOROTHIAZIDE; FAMOTIDINE; GASTROINTESTINAL AGENT; METFORMIN; NICOTINE; PENICILLIN G; PROCAINAMIDE; QUINOLINE DERIVED ANTIINFECTIVE AGENT;

ADULT; AREA UNDER THE CURVE; ARTICLE; DRUG DISPOSITION; DRUG ELIMINATION; DRUG EXCRETION; GLOMERULUS FILTRATION; HUMAN; HYDROPHILICITY; IONIZATION; KIDNEY CLEARANCE; KIDNEY TUBULE ABSORPTION; LIPOPHILICITY; NORMAL HUMAN; PASSIVE TRANSPORT; PHYSICAL CHEMISTRY;

HUMANS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; HYDROPHOBICITY; KIDNEY; METABOLIC CLEARANCE RATE; MOLECULAR WEIGHT;

EID: 68549122719     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900403j     Document Type: Article

References (48)

1. Masereeuw, R.; Russel, F. G. Mechanisms and clinical implications of renal drug excretion. Drug Metab. Rev. 2001, 33, 299-351.
2. Fagerholm, U. Prediction of human pharmacokinetics: renal metabolic and excretion clearance. J. Pharm. Pharmacol. 2007, 59, 1463-1471.
3. Roffey, S. J.; Obach, R. S.; Gedge, J. I.; Smith, D. A. What is the objective of the mass balance study? A retrospective analysis of data in animal and human excretion studies employing radiolabeled drugs. Drug Metab. Rev. 2007, 39, 17-43.
4. Roland, M.; Tozer, T. N. Clinical Pharmacokientics: Concepts and Applications; Williams & Wilkins: Baltimore, MD, 1995.
5. Walton, K.; Dorne, J. L.; Renwick, A. G. Species-specific uncertainty factors for compounds eliminated principally by renal excretion in humans. Food Chem. Toxicol. 2004, 42, 261-274.
6. Ho, R. H.; Kim, R. B. Transporters and drug therapy: implications for drug disposition and disease. Clin. Pharmacol. Ther. 2005, 78, 260-277.
7. Shitara, Y.; Sato, H.; Sugiyama, Y. Evaluation of drug-drug interaction in the hepatobiliary and renal transport of drugs. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 689-723.
8. Li, M.; Anderson, G. D.; Wang, J. Drug-drug interactions involving membrane transporters in the human kidney. Expert Opin. Drug Metab. Toxicol. 2006, 2, 505-532.
9. Sun, H.; Frassetto, L.; Benet, L. Z. Effects of renal failure on drug transport and metabolism. Pharmacol. Ther. 2006, 109, 1-11.
10. Jappar, D.; Hu, Y.; Keep, R. F.; Smith, D. E. Transport mechanisms of carnosine in SKPT cells: contribution of apical and basolateral membrane transporters. Pharm. Res. 2009, 26, 172-181.
11. Koepsell, H.; Lips, K.; Volk, C. Polyspecific organic cation transporters: structure, function, physiological roles, and biopharmaceutical implications. Pharm. Res. 2007, 24, 1227-1251.
12. El-Sheikh, A. A.; Masereeuw, R.; Russel, F. G. Mechanisms of renal anionic drug transport. Eur. J. Pharmacol. 2008, 585, 245-255.
13. van de Water, F. M.; Masereeuw, R.; Russel, F. G. Function and regulation of multidrug resistance proteins (MRPs) in the renal elimination of organic anions. Drug Metab. Rev. 2005, 37, 443-471.
14. Ci, L.; Kusuhara, H.; Adachi, M.; Schuetz, J. D.; Takeuchi, K.; Sugiyama, Y. Involvement of MRP4(ABCC4) in the luminal efflux of ceftizoxime and cefazolin in the kidney. Mol. Pharmacol. 2007, 71, 1591-1597.
15. Shitara, Y.; Horie, T.; Sugiyama, Y. Transporters as a determinant of drug clearance and tissue distribution. Eur. J. Pharm. Sci. 2006, 27, 425-446.
16. Winiwarter, S.; Bonham, N. M.; Ax, F.; Hallberg, A.; Lennernas, H.; Karlen, A. Correlation of human jejunal permeability (in vivo) of drugs with experimentally and theoretically derived parameters. A multivariate data analysis approach. J. Med. Chem. 1998, 41, 4939-4949.
17. Kelder, J.; Grootenhuis, P. D.; Bayada, D. M.; Delbressine, L. P.; Ploemen, J. P. Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm. Res. 1999, 16, 1514-1519.
18. Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44, 235-249.
19. Kubinyi, H. Lipophilicity and biological acitivity. Drug transport and drug distribution in model systems and in biological systems. Arzneimittelforschung 1979, 29, 1067-1080.
20. Obach, R. S.; Lombardo, F.; Waters, N. J. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug Metab. Dispos. 2008, 36, 1385-1405.
21. Thummel, K. E.; Shen, D. D. Design and Optimization of Dosage Regimens: Pharmacokinetic Data. In Goodman and Gillman's the Pharmacological Basis of Therapeutics,10th ed.; Hardman, J. G., Limbird, L. E., Goodman Gilman, A., Eds.; McGraw-Hill: New York, 2001; pp 1917-2024.
22. Doddareddy, M. R.; Cho, Y. S.; Koh, H. Y.; Kim, D. H.; Pae, A. N. In silico renal clearance model using classical Volsurf approach. J. Chem. Inf. Model. 2006, 46, 1312-1320.
23. Wenlock, M. C.; Austin, R. P.; Barton, P.; Davis, A. M.; Leeson, P. D. A comparison of physiochemical property profiles of development and marketed oral drugs. J. Med. Chem. 2003, 46, 1250-1256.
24. Doherty, A. In Annual Reports in Medicinal Chemistry; Academic Press: San Diego, CA, 2003; Vol. 38, pp 425-441.
25. Leeson, P. D.; Davis, A. M. Time-related differences in the physical property profiles of oral drugs. J. Med. Chem. 2004, 47, 6338-6348.
26. Goodwin, J. T.; Conradi, R. A.; Ho, N. F.; Burton, P. S. Physicochemical determinants of passive membrane permeability: role of solute hydrogen-bonding potential and volume. J. Med. Chem. 2001, 44, 3721-3729.
27. Varma, M. V.; Sateesh, K.; Panchagnula, R. Functional role of Pglycoprotein in limiting intestinal absorption of drugs: contribution of passive permeability to P-glycoprotein mediated efflux transport. Mol. Pharmaceutics 2005, 2, 12-21.
28. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45, 2615-2623.
29. Gleeson, M. P. Generation of a set of simple, interpretable ADMET rules of thumb. J. Med. Chem. 2008, 51, 817-834.
30. Bednarczyk, D.; Ekins, S.; Wikel, J. H.; Wright, S. H. Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol. Pharmacol. 2003, 63, 489-498.
31. Ullrich, K. J. Renal transporters for organic anions and organic cations. Structural requirements for substrates. J. Membr. Biol. 1997, 158, 95-107.
32. Ahlin, G.; Karlsson, J.; Pedersen, J. M.; Gustavsson, L.; Larsson, R.; Matsson, P.; Norinder, U.; Bergstrom, C. A.; Artursson, P. Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. J. Med. Chem. 2008, 51, 5932-5942.
33. Inui, K. I.; Masuda, S.; Saito, H. Cellular and molecular aspects of drug transport in the kidney. Kidney Int. 2000, 58, 944-958.
34. Launay-Vacher, V.; Izzedine, H.; Karie, S.; Hulot, J. S.; Baumelou, A.; Deray, G. Renal tubular drug transporters. Nephron Physiol. 2006, 103, 97-106.
35. Ayrton, A.; Morgan, P. Role of transport proteins in drug absorption, distribution and excretion. Xenobiotica 2001, 31, 469-497.
36. Takeda, M.; Khamdang, S.; Narikawa, S.; Kimura, H.; Hosoyamada, M.; Cha, S. H.; Sekine, T.; Endou, H. Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J. Pharmacol. Exp. Ther. 2002, 302, 666-671.
37. Inotsume, N.; Nishimura, M.; Nakano, M.; Fujiyama, S.; Sato, T. The inhibitory effect of probenecid on renal excretion of famotidine in young, healthy volunteers. J. Clin. Pharmacol. 1990, 30, 50-56.
38. Bendayan, R.; Sullivan, J. T.; Shaw, C.; Frecker, R. C.; Sellers, E. M. Effect of cimetidine and ranitidine on the hepatic and renal elimination of nicotine in humans. Eur. J. Clin. Pharmacol. 1990, 38, 165-169.
39. Kirch, W.; Rose, I.; Demers, H. G.; Leopold, G.; Pabst, J.; Ohnhaus, E. E. Pharmacokinetics of bisoprolol during repeated oral administration to healthy volunteers and patients with kidney or liver disease. Clin. Pharmacokinet. 1987, 13, 110-117.
40. Somogyi, A.; Stockley, C.; Keal, J.; Rolan, P.; Bochner, F. Reduction of metformin renal tubular secretion by cimetidine in man. Br. J. Clin. Pharmacol. 1987, 23, 545-551.
41. O'Shea, R.; Moser, H. E. Physicochemical properties of antibacterial compounds: implications for drug discovery. J. Med. Chem. 2008, 51, 2871-2878.
42. Mahar Doan, K. M.; Humphreys, J. E.; Webster, L. O.; Wring, S. A.; Shampine, L. J.; Serabjit-Singh, C. J.; Adkison, K. K.; Polli, J. W. Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J. Pharmacol. Exp. Ther. 2002, 303, 1029-1037.
43. van de Waterbeemd, H.; Camenisch, G.; Folkers, G.; Chretien, J. R.; Raevsky, O. A. Estimation of blood-brain barrier crossing of drugs using molecular size and shape, and H-bonding descriptors. J. Drug Targeting 1998, 6, 151-165.
44. Takeda, M.; Babu, E.; Narikawa, S.; Endou, H. Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur. J. Pharmacol. 2002, 438, 137-142.
45. Khamdang, S.; Takeda, M.; Babu, E.; Noshiro, R.; Onozato, M. L.; Tojo, A.; Enomoto, A.; Huang, X. L.; Narikawa, S.; Anzai, N.; Piyachaturawat, P.; Endou, H. Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur. J. Pharmacol. 2003, 465, 1-7.
46. Jariyawat, S.; Sekine, T.; Takeda, M.; Apiwattanakul, N.; Kanai, Y.; Sophasan, S.; Endou, H. The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J. Pharmacol. Exp. Ther. 1999, 290, 672-677.
47. Ullrich, K. J.; Rumrich, G.; David, C.; Fritzsch, G. Bisubstrates: substances that interact with both, renal contraluminal organic anion and organic cation transport systems. II. Zwitterionic substrates: dipeptides, cephalosporins, quinolone-carboxylate gyrase inhibitors and phosphamide thiazine carboxylates; nonionizable substrates: steroid hormones and cyclophosphamides. Pfluegers Arch. 1993, 425, 300-312.
48. TP Search-Transporter database. TP-Search Production Committee. http://125.206.112.67/tp-search/index.html (accessed Feb 2009).