Correlations between factors determining the pharmacokinetics and antiviral activity of HIV-1 non-nucleoside reverse transcriptase inhibitors of the diaryltriazine and diarylpyrimidline classes of compounds

Drugs in R and D

Volumn 5, Issue 5, 2004, Pages 245-257

  Lewi, Paul ^a   Arnold, Eddy ^b   Andries, Koen ^c   Bohets, Hilde ^d   Borghys, Herman ^d   Clark, Arthur ^b   Daeyaert, Frits ^a   Das, Kaylan ^b   de Béthune, Marie Pierre ^c   de Jonge, Marc ^a   Heeres, Jan ^a   Koymans, Luc ^a   Leempoels, Jos ^d   Peeters, Jef ^d   Timmerman, Philip ^d   Van den Broeck, Walter ^a   Vanhoutte, Frédéric ^d   van't Klooster, Gerben ^c   Vinkers, Maarten ^a   Volovik, Yulia ^b   Janssen, Paul A J ^a   more..

^a Center for Molecular Design   (Belgium)

^b RUTGERS UNIVERSITY   (United States)

^c Virco BVBA   (Belgium)

^d JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; DAPIVIRINE; DIARYLPYRIMIDINE DERIVATIVE; DIARYLTRIAZINE DERIVATIVE; ETRAVIRINE; OCTANOL; R 106168; R 120393; R 124043; R 126874; R 129385; R 132914; R 138750; R 152649; R 152929; R 156204; R 157753; R 185445; R 185545; RNA DIRECTED DNA POLYMERASE INHIBITOR; SOLVENT; UNCLASSIFIED DRUG; WATER;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIVIRAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CALCULATION; CELL ASSAY; CELL STRAIN CACO 2; CLINICAL STUDY; CLINICAL TRIAL; CONCENTRATION RESPONSE; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CORRELATION FUNCTION; DOG; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLASSIFICATION; DRUG EXPOSURE; DRUG METABOLISM; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG TRANSPORT; DRUG UPTAKE; ENDOCYTOSIS; ENERGY; EPITHELIUM; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IN VIVO STUDY; INTESTINE ABSORPTION; IONIZATION; LIPOPHILICITY; LYMPHATIC SYSTEM; MOLECULAR MECHANICS; NONHUMAN; PARTITION COEFFICIENT; PHARMACOLOGICAL PARAMETERS; PHASE 1 CLINICAL TRIAL; PHENOMENOLOGY; PHYSICAL CHEMISTRY; PREDICTION; PRIORITY JOURNAL; RAT; SOLVATION; SURFACE PROPERTY; VIRUS REPLICATION; VOLUNTEER;

ANIMALS; ANTI-HIV AGENTS; AREA UNDER CURVE; BIOLOGICAL AVAILABILITY; CACO-2 CELLS; DOGS; HIV-1; HUMANS; INTESTINAL ABSORPTION; LYMPH; MODELS, MOLECULAR; PYRIMIDINES; RATS; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

EID: 7244229886     PISSN: 11745886     EISSN: None     Source Type: Journal    
DOI: 10.2165/00126839-200405050-00001     Document Type: Article

References (38)

1. Pauwels R, Andries K, Desmyter J, et al. Potent and selective inhibition of HIV-1 replication in vitro by a novel series of TIBO derivatives. Nature 1990, 343: 470-4
2. Ludovici DW, Kukla MJ, Grous PG, et al. Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinopheny-lacetamide (alpha-APA) to imidoyl thiourea (ITU). Bioorg Med Chem Lett 2001; 11: 2225-8
3. Ludovici DW, Kavash RW, Kukla MJ, et al. Evolution of anti-HIV drug candidates. Part 2: Diaryltriazine (DATA) analogues. Bioorg Med Chem Lett 2001; 11: 2229-34
4. Ludovici DW, De Corte BL,,Kukla MY, et al. Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues. Bioorg Med Chem Lett 2001; 11: 2235-9
5. Kohlstaedt LA, Wang J, Friedman JM et al. Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science 1992; 256: 1783-90
6. Ding J, Das K, Moereels H, et al. Structure of HIV-1 RT/TIBO R 86183 complex reveals similarity in the binding of diverse nonnucleoside inhibitors. Nat Struct Biol 1995; 2: 407-15
7. Ding J, Das'K, Tantillo C, et al. Structure of HIV-1 reverse transcriptase in a complex with the non-nucleoside inhibitor alpha-APA R 95845 at 2.8 A resolution. Structure 1995; 3: 365-79
8. Das K, Clark AD, Lewi P, et al. Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (Etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants. J Med Chem 2004; 47. 2250-560
9. Mager PP. Evidence of a butterfly-like configuration of structurally diverse allosteric inhibitors of the HIV-1 reverse transcriptase. Drug Des Discov 1996: 14: 241-57
10. Lewi PJ, de Jonge M, Daeyaert F, et al. On the detection of multiple-binding modes of ligands to proteins, from biological, structural and modeling data. J Comput Aided Mol Des 2003; 17: 129-34
11. Van de Waterbeemd H, Smith DA, Beaumont K, et al. Property-based design: optimization of drug absorption and pharmacokinetics. J Med Chem 2001: 44: 1313-33
12. Bohets H, Annaert P, Mannens G, et al. Strategies for drug screening in drug discovery and development. Curr Top Med Chem 2001: 1: 367-83
13. Pauwels R, Balzarini J, Baba M, et al. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J Virol Methods 1988: 20: 309-21
14. Daylight Software 4.41 Daylight Chemical Infornnation Systems Inc., Irvine (CA). 1995
15. Dynapro. Dynamic light scattering instruments. Charlottesville (VA): Protein Solutions UK Ltd. 2003
16. Skouri M, Delsanti M, Munch JP, et al. Dynamic light scattering, studies of the aggregation of lysozyme under crystallization conditions. FEBS Lett 1991: 295: 84-8
17. Connolly ML. Solvent-accessible surfaces of proteins and nucleic acids. Science 1983: 221: 709-13
18. Still WC, Tempczyck A. Hawley RC, et al. Semianalytical treatment of solvation for molecular mechanics and dynamics. J Am Chem Soc 1990: 112: 6127-9
19. Siegel S, Castellan NJ. Nonparametric statistics for the behavioral sciences. New York: McGraw-Hill, 1988
20. Stella VJ, Charman WN. Lymphatic transport of drugs. London Tokyo: CRC Press. 1992
21. Popper H. Distribution of vitamin A in tissue as visualized by fluorescence microscopy. Physiol Rev 1944: 24: 205-24
22. Porter CJ, Charman WN. Intestinal lymphatic drug transport: an update. Adv Drug Deliv Rev 2001: 50: 61-80
23. Porter CJ, Charman WN. Uptake of drugs into the intestinal lymphatics after oral administration. Adv Drug Deliv Rev 1997: 25: 71-89
24. McGovern SL, Caselli E, Grigorieff N, et al. A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. J Med Chem 2002: 45: 1712-22
25. McGovern SL, Helfland BT, Feng B, et al. A specific mechanism of non-specific inhibition. J Med Chem 2003. 46: 4265-72
26. Seidler J, McGovern SL, Doman TN, et al. Identification and prediction of promiscuous aggregating inhibitors among known drugs. J Med Chem 2003; 46: 4477-86
27. Madara JL. The chameleon within: improving antigen delivery. Science 1997; 277: 910-1
28. Niedergang F, Kraehenbuhl JP. Much ado about M cells. Trends Cell Biol 2000; 10: 137-41
29. Yeh P-Y, Ellens H, Smith PL. Physiological considerations in the design of particulate dosage forms for oral vaccine delivery. Adv Drug Deliv Rev 1998; 34: 123-33
30. Neutra MR. Current concepts in mucosal immunity: V. Role of M cells in transpithelial transport of antigens and pathogens to the mucosal immune system. Am J Physiol 1998: 274: G785-91
31. Kaiserlian D, Etchart N. Entry sites for oral vaccines and drugs: a role for M cells, enterocytes and dendritic cells? Semin Immunol 1999; 11: 217-24
32. Florence AT, Hussain N. Transcytosis of nanoparticle and dendrimer delivery systems: evolving vistas. Adv Drug Deliv Rev 2001: 50 Suppl. 1: S69-89
33. Florence AT. The oral absorption of micro- and nanoparticulates: neither exceptional nor unusual. Pharm Res 1997: 14: 259-66
34. Dorland WA. Dorland's illustrated medical dictionary. Philadelphia (PA): Saunders. 1981: 761
35. Wang L, Robb CW, Cloyd MW. HIV induces homing of resting T lymphocytes to lymph nodes. Virology 1997; 228: 141-52
36. Tamalet C, Lafeuillade A, Yahi N, et al. Comparison of viral burden and phenotype of HIV-1 isolates from lymph nodes and blood. AIDS 1994: 8: 1083-8
37. Pantaleo G, Cohen OJ. Schacker T, et al. Evolutionary pattern of human immunodeficiency virus (HIV) replication and distribution in lymph nodes following primary infection: implications for antiviral therapy. Nat Med 1998: 4: 341-5
38. Zhao YH, Le J, Abraham MH, et al. Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors. J Pharm Sci 2001, 90: 749-84