Human immunodeficiency virus protease inhibitors From drug design to clinical studies

Advanced Drug Delivery Reviews

Volumn 27, Issue 2-3, 1997, Pages 215-233

  Lin, Jiunn H ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

CYP 3A4; Drug drug desgn; Enzyme induction; Indinavir; Ritonavir; Saquinavir; Substrate structure based on drug design

Indexed keywords

ABSORPTION; BLOOD; DISEASES; DRUG INTERACTIONS; DRUG THERAPY; ENZYME INHIBITION; HEALTH CARE; METABOLISM; PROTEINS;

CYTOCHROME; HUMAN IMMUNODEFICIENCY; INDINAVIR; ORAL BIOAVAILABILITY; RITONAVIR; SAQUINAVIR; VIRUS PROTEASE INHIBITORS;

PHARMACOKINETICS;

A 77003; A 80987; CLARITHROMYCIN; DESIPRAMINE; DEXTROMETHORPHAN; INDINAVIR; NIFEDIPINE; PROTEINASE INHIBITOR; RIFABUTIN; RIFAMPICIN; RITONAVIR; SAQUINAVIR; STAVUDINE; TERFENADINE; ZALCITABINE; ZIDOVUDINE;

DOG; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG METABOLISM; DRUG PROTEIN BINDING; DRUG TRANSPORT; ENZYME INDUCTION; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; MONKEY; NONHUMAN; ORAL DRUG ADMINISTRATION; PHARMACOKINETICS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RAT; REVIEW;

EID: 0342940805     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(97)00044-6     Document Type: Review

References (58)

1. Hirsch M.S., D'Aquila R.T. Therapy for human immunodeficiency virus infection. New Engl. J. Med. 328:1993;1686-1695.
2. Langtry H.D., Campoli-Richards D.M. Zidovudine: A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy. Drugs. 37:1989;408-450.
3. Moyle G. Resistance to antiretroviral compounds: Implications for the clinical management of HIV infection. Immunol. Infect. Dis. 5:1995;170-182.
4. Huff J.R. HIV protease: A novel chemotherapeutic target for AIDS. J. Med. Chem. 34:1993;2305-2314.
5. Darke P.L., Huff J.R. HIV protease as an inhibitor target for the treatment of AIDS. Adv. Pharmacol. 25:1994;399-454.
6. Vacca J.P., Dorsey B.D., Schleif W.A., Levin R.B., McDaniel S.L., Darke P.L., Zugay J., Quintero J.C., Blahy O.M., Roth E., Sardana V.V., Schlabach A.J., Graham P.L., Condra J.H., Gotlib L., Holloway M.K., Lin J.H., Chen I.-W., Vastag K., Ostovic D., Anderson P.S., Emini E.A., Huff J.R. L-735,524: An orally bioavailable human immunodeficiency virus type 1 protease inhibitor. Proc. Natl. Acad. Sci. 91:1994;4096-4100.
7. Tomasselli A.G., Howe W.J., Sawyer T.K., Wlidawer A., Heinrikson R.L. The complexities of AIDS: An assessment of the HIV protease as a therapeutic target. Chim. Oggi. 9:1991;6-27.
8. Roberts N.A., Martin J.A., Kinchington D., Broadhurst A.V., Craig J.C., Duncan I.B., Galpin S.A., Handa B.K., Kay J., Kröhn A., Lambert R.W., Merrett J.H., Mills J.S., Parkes K.E.B., Redshaw S., Ritchie A.J., Taylor D.L., Thomas G.J., Machin P.J. Rational design of peptide-based HIV protease inhibitors. Science. 248:1990;358-361.
9. Redshow S. Inhibitors of HIV protease. Exp. Opin. Invest. Drugs. 3:1994;273-286.
10. Wlidawer A., Erickson J.W. Structure-based inhibitors of HIV-1 protease. Annu. Rev. Biochem. 62:1993;543-585.
11. Swain A.L., Miller M.M., Green J., Rich D.H., Schneider J., Kent S.B.H., Wlidawer A. X-ray crystallographic structure of a complex between a synthetic substrate-based hydroxyethylamine inhibitor. Proc. Natl. Acad. Sci. USA. 87:1990;8805-8809.
12. Kempf D.J., Marsh K.C., Fino L.C., Bryant P., Craig-Kennard A., Sham H.L., Zhao C., Vasavanonda S., Kohlbrenner W.E., Wideburg N.E., Saldivar A., Green B.E., Herrin T., Norbeck D.W. Design of orally bioavailable, symmetry-based inhibitors of HIV protease. Bioorg. Med. Chem. 2:1994;847-858.
13. Kempf D.J., March K.C., Denissen J.F., McDonald E., Vasavanonda S., Flentge C.A., Green B.E., Fino L., Park C.H., Long X.-P., Wideburg N.E., Saldivar A., Ruiz L., Kati W.M., Sham H.L., Robins T., Stewart K.D., Hsu A., Plattner J.J., Leonard J.M., Norbeck D.W. ABT-538 is a potent inhibitor of human immunodeficiency virus protease and has high oral bioavailability in humans. Proc. Natl. Acad. Sci. USA. 92:1995;2484-2488.
14. Kempf D.J., Marsh K.C., Paul D.A., Knigge M.K., Norbeck D.W., Kohlbrenner W.E., Codacovi L., Vasavanonda S., Bryant P., Wang X.C., Wideburg N.E., Clement J.J., Plattner J.J., Erickson J. Antiviral and pharmacokinetic properties of C2 symmetric inhibitors of the human immunodeficiency virus type 1 protease. Antimicrob. Agents Chemother. 35:1991;2209-2214.
15. Wlodawer A., Miller M., Jaskolski M., Sathyanarayana B.K., Baldwin E., Weber I.T., Selk L.M., Clawson L., Schneider J., Kent S.B.H. Conserved folding in retroviral proteases: Crystal structure of a synthetic HIV protease. Science. 245:1989;616-621.
16. D.E. Deahy, J. Lynch, D.D. Taylor, Mechanisms of absorption of small molecules, in: L.F. Prescott, W.S. Nimmo (Eds.), Novel Drug Delivery, Wiley, New York, 1989, Chap. 4, pp. 33-44.
17. Leo A., Hansch C., Elkins D. Partition coefficients and their use. Chem. Res. 71:1971;525-565.
18. Schanker L.S. On the mechanism of absorption from the gastrointestinal tract. J. Med. Pharm. Chem. 2:1960;343-346.
19. Taylor D.C., Downall R., Burke W. The absorption of β-adrenoceptor antagonists in rat in situ small intestine: The effect of lipophilicity. J. Pharm. Pharmacol. 37:1985;280-282.
20. J.K. Seydel, K.J. Schaper, Quantitative structure-pharmacokinetic relationships and drug design, in: M. Rowland, G. Tucker (Eds.), Pharmacokinetics: Theory and Methodology, Pergamon, New York, 1986, Chap. 13, pp. 311-366.
21. Toon S., Rowland M. Structure-pharmacokinetic relationships among the barbiturates in the rat. J. Pharmacol. Exp. Ther. 225:1983;752-763.
22. Dorsey B.D., McDaniel S.L., Levin R.B., Vacca J.P., Darke P.L., Zugay J.A., Emini E.A., Schleif W.A., Lin J.H., Chen I.-W., Holloway M.K., Anderson P.S., Huff J.R. Synthesis and evaluation of pyridyl analogs of L-735,524: potent HIV-1 protease inhibitors. Bioorg. Med. Chem. Lett. 4(23):1994;2769-2774.
23. Lin J.H., Chen I.-W., Vastag K.J., Ostovic D. pH-dependent oral absorption of L-735,524, a potent HIV protease inhibitor in rats and dogs. Drug Metab. Dispos. 23:1995;730-735.
24. Williams P.E.O., Muirhead G.J., Madigan J., Mitchell A.M., Shaw T.M. Disposition and bioavailability of the HIV protease inhibitor R031-8959 after single dose in healthy volunteers. Br. J. Chem. Pharmacol. 34:1992;155p-156p.
25. J.L. Campra, T.B. Reynolds, The hepatic circulation, in: I.M. Arias, W.B. Jakoby, H. Popper, D. Schachter, D.A. Shafritz (Eds.), The Liver: Biology and Pathobiology, Raven Press, 1988, Chap. 2, pp. 911-930.
26. Hoffman-LaRoche. R031-8959 Saquinavir Invirase™. Investigational Drug Brochure, 1995.
27. Shaw T.M., Muirhead G.J., Parish N., McClelland G.R., Houston A.C. Tolerability and pharmacokinetics of single oral doses of RO318959, an HIV protease inhibitor. Br. J. Clin. Pharmacol. 34:1992;166p-167p.
28. Muirhead G.T., Shaw T., Williams P.E.P., Madigan M.J., Mitchell A.M., Houston A.C. Pharmacokinetics of the HIV protease inhibitor, RO318959, after single and multiple oral doses in healthy volunteers. Br. J. Clin. Pharmacol. 34:1992;170p-171p.
29. Invirase. Roche Laboratories, Prescribing Information from Physicians' Desk Reference, 1996.
30. Roberts N.A., Craig J.C., Duncan I.B. HIV protease inhibitors. Biochem. Soc. Trans. 20:1992;513-516.
31. Lin J.H., Chiba M., Balani S.K., Chen I.-W., Kwei G.Y.-S., Vastag K.J., Nishime J.A. Species differences in the pharmacokinetics and metabolism of indinavir, a potent human immunodeficiency virus protease inhibitor. Drug Metab. Dispos. 24:1996;1111-1120.
32. Panteleo G., Braziosi C., Demarest J.F., Butini L., Montroni M., Fox C.H., Orenstein J.M., Kotler D.P., Fauci A.S. HIV infection is active and progressive in lymphoid tissue during the clinically latent stage of disease. Nature. 362:1993;355-358.
33. Embreston J., Zupancic M., Ribas J.L., Burke A., Racz P., Tenner-Racz K., Haase A.T. Massive covert infection of helper T lymphocytes by HIV during the incubation period of AIDS. Nature. 363:1993;359-362.
34. Stone J.A., Ju W.D., Steritt A., Woolf E.J., Yeh K.C., Deutsch P., Waldman S., Bjornsson T.D. Effect of food on the pharmacokinetics of indinavir in man. Pharm. Res. 13:1996;S414.
35. Lin J.H., Sugiyama Y., Awazu S., Hanano M. Physiological pharmacokinetics of ethoxybenzamide based on biochemical data obtained in vitro as well as on physiological data. J. Pharmacokinet. Biopharm. 10:1982;649-661.
36. Dedrick R.L., Zaharko D.S., Lutz R.L. Transport and binding of methotrexate in vivo. J. Pharm. Sci. 62:1973;882-890.
37. S.K. Balani, E.J. Woolf, V.L. Hoagland, M.G. Sturgill, P.J. Deutsch, K.C. Yeh, J.H. Lin, Disposition of indinavir, a potent HIV-1 protease inhibitor, after an oral dose in humans. Drug Metab. Dispos. (1997) in press.
38. Norvir, Abbott, Prescribing Information from Physicians' Desk Reference, 1996.
39. Lin J.H. Dose-dependent pharmacokinetics: Experimental observations and theoretical considerations. Biopharm. Drug Dispos. 15:1994;1-31.
40. R.H. Levy, Time-dependent pharmacokinetics, in: M. Rowland, G. Tucker (Eds.), Pharmacokinetics: Theory and Methodology, Pergamon, New York, 1986, pp. 115-129.
41. Bilello J.A., Bilello P.A., Prichard M., Robins T., Drusano G.L. Reduction of the in vitro activity of A77003, an inhibitor of human immunodeficiency virus protease by serum α1-acid glycoprotein. J. Infect. Dis. 717:1995;546-551.
42. Kageyama S., Anderson B.D., Hoesterey B.L., Hayashi H., Kiso Y., Flora K.P., Mitsuya H. Protein binding of human immunodeficiency virus protease inhibitor KNI-272 and alteration of its in vitro antiretroviral activity in the presence of high concentration of proteins. Antimicrob. Agents Chemother. 38:1994;1107-1111.
43. Farrar G., Mitchell A.M., Hooper H., Stewart F., Malcolm S.L. Prediction of potential drug interactions of saquinavir (RO31-8959) from in vitro data. Br. J. Clin. Pharmacol. 38:1994;162p.
44. Balani S.K., Arison B.H., Mathai L., Kauffman L.R., Miller R.R., Stearns R.A., Chen I.-W., Lin J.H. Metabolites of L-735,524, a potent HIV-1 protease inhibitor, in human urine. Drug Metab. Dispos. 23:1995;266-270.
45. Chiba M., Hensleigh M., Nishime J., Balani S.K., Lin J.H. Role of cytochrome P450 3A4 in human metabolism of MK-639, a potent human immunodeficiency virus protease inhibitor. Drug Metab. Dispos. 24:1996;307-314.
46. Chiba M., Hensleigh M., Lin J.H. Hepatic and intestinal metabolism of indinavir, an HIV protease inhibitor, in rat and human microsomes. Biochem. Pharmacol. 53:1996;1187-1195.
47. Houston J.B. Utility of in vitro drug metabolism data in prediction of in vivo metabolic clearance. Biochem. Pharmacol. 47:1994;1469-1479.
48. Born P.J.A., Frankhuizen-Sierevogel A., Noordhoek J. Time and dose dependence of 3-methylcholanthrene-induced metabolism in rat intestinal mucosal cells and microsomes. Biochem. Pharmacol. 31:1982;3707-3710.
49. Pang K.S., Rowland M. Hepatic clearance of drugs. I. Theoretical consideration of a "well-stirred" model and a "parallel-tube model". Influence of hepatic blood flow, plasma and blood cells binding, and the hepatocellular activity on hepatic drug clearance. J. Pharmacokinet. Biopharm. 5:1977;625-653.
50. Lin J.H., Chiba M., Chen I.-W., Nishime J.A., Vastag K.J. Sex-dependent pharmacokinetics of indinavir: In vivo and in vitro evidence. Drug Metab. Dispos. 24:1996;0000-0000.
51. Crixivan, Merck, Prescribing Information from Physicians' Desk Reference, 1997, p. 1670-1673.
52. Kumar G.N., Rogrigues A.D., Buko A.M., Denisson J.F. Cytochrome P450-mediated metabolism of the HIV-1 protease inhibitor ritonavir (ABT-538) in human liver microsomes. J. Pharmacol. Exp. Ther. 277:1996;423-431.
53. Dudley M.N. Clinical pharmacokinetics of nucleoside antiretroviral agents. J. Infect. Dis. 7(suppl):1995;S99-S112.
54. Wilde M.I., Langtry H.D. Zidovudine: An update of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy. Drugs. 46:1995;515-578.
55. Benedetti M.S. Inducing properties of rifabutin, and effects on the pharmacokinetics and metabolism of concomitant drugs. Pharmacol. Res. 32:1955;177-187.
56. Venkatesan K. Pharmacokinetic drug interactions with rifampicin. Clin. Pharmacokinet. 22:1992;47-65.
57. McCrea J., Woolf E., Sterrett A., Matthews C., Deutsch P., Yeh K.C., Waldman S., Bjornsson T. Effects of ketoconazole and other P-450 inhibitors on the pharmacokinetics of indinavir. Pharm. Res. 13:1996;S485.
58. Winchell G.A., McCrea J.B., Tomasko L., Kusma S.E., Chiou R., Deutsch P., Yeh K.C., Strugill M., Borucholl S. Study of potential pharmacokinetic interaction between indinavir and clarithromycin. Pharm. Res. 13:1996;S434.