Clinical pharmacokinetics of the antiviral nucleotide analogues cidofovir and adefovir

Clinical Pharmacokinetics

Volumn 36, Issue 2, 1999, Pages 127-143

  Cundy, Kenneth C ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADEFOVIR; ADEFOVIR DIPIVOXIL; ANTIVIRUS AGENT; CIDOFOVIR; PROBENECID; PRODRUG;

ANTIVIRAL ACTIVITY; CYTOMEGALOVIRUS INFECTION; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG ELIMINATION; DRUG EXCRETION; DRUG METABOLISM; HEPADNAVIRUS; HERPES VIRUS; HUMAN; INTRAVENOUS DRUG ADMINISTRATION; PAPILLOMA VIRUS; POXVIRUS; PRIORITY JOURNAL; RETINITIS; RETROVIRUS; REVIEW; SUBCUTANEOUS DRUG ADMINISTRATION;

EID: 0032997095     PISSN: 03125963     EISSN: None     Source Type: Journal    
DOI: 10.2165/00003088-199936020-00004     Document Type: Review

References (63)

1. 1. Bronson JJ, Ferrara LM, Hitchcock MJM, et al. (S)-1-(3-Hydroxy-2-(phosphonylmethoxy)propyl) cytosine (HPMPC): a potent antiherpesvirus agent. In: Lopez C, Mori R, Roizman B, et al., editors. Immunobiology and prophylaxis of human herpesvirus infections. New York: Plenum Press, 1990
2. 2. Balzarini J, Naesens L, Herdewijn P, et al. Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent. Proc Natl Acad Sci USA 1989; 86: 332-6
3. 3. Bronson JJ, Ho H-T, De Boeck H, et al. Biochemical pharmacology of acyclic nucleotide analogs. Ann NY Acad Sci 1990; 616: 398-407
4. 4. Safrin S. Treatment of acyclovir resistant herpes simplex virus infections in patients with AIDS. J Acquir Immune Defic Syndr 1992; 5 Suppl.: S29-32
5. 5. Naesens L, Snoeck R, Andrei G, et al. HPMPC (cidofovir), PMEA (adefovir) and related acyclic nucleoside phosphonate analogues: a review of their pharmacology and clinical potential in the treatment of viral infections. Antiviral Chem Chemother 1997; 8(1): 1-23
6. 6. Ho H-T, Woods KL, Bronson JJ, et al. Intracellular metabolism of the antiherpes agent (S)-1-[3-hydroxy-2-phosphonyl-methoxy)propyl]-cytosine. Mol Pharmacol 1992; 41: 197-202
7. 7. Aduma P, Connelly MC, Srinivas RV, et al. Metabolic diversity and antiviral activities of acyclic nucleoside phosphonates. Mol Pharmacol 1995 47: 816-22
8. 8. Lalezari JP, Stagg RJ, Kuppermann BD, et al. Intravenous cidofovir for peripheral cytomegalovirus retinitis in patients with AIDS. Ann Intern Med 1997; 126: 257-63
9. 9. Lalezari J, Schaker T, Feinberg J, et al. A randomized, double-blind, placebo-controlled trial of cidofovir gel for the treatment of acyclovir-unresponsive mucocutaneous herpes simplex virus infection in patients with AIDS. J Infect Dis 1997; 176: 892-8
10. 10. Kriesel J, Douglas J, Corey L, et al. A phase I/II study of cidofovir gel for refractory condyloma acuminatum in patients with HIV-infection [abstract no. 334]. Program and Abstracts of the 4th Conference on Retroviruses and Opportunistic Infections; 1997 Jan 22-25: Washington, DC
11. 11. Walker RE, Vogel SE, Jaffe HS, et al. A phase I/II study of PMEA in HIV-infected patients [abstract no. 522]. First National Conference on Humun Retroviruses and Related Infections; 1993 Dec 12-16;148
12. 12. Cundy KC, Petty BG, Flaherty J, et al. Clinical pharmacokinetics of cidofovir in HIV-infected patients. Antimicrob Agents Chemother 1995; 39: 1247-52
13. 13. Snoeck R, DeWit S, Rossi C, et al. Treatment of progressive multifocal leukoencephalopathy (PML) with cidofovir in an AIDS patient [abstract]. Antiviral Res 1996; 30: A51
14. 14. Eisenberg EJ, Cundy KC. HPLC determination of cytosine containing compounds by precolumn fluorescence derivatization with phenacyl bromide: application to antiviral nucleosides and nucleotides. J Chomatogr Biomed Appl 1996; 679: 119-27
15. 15. Russell JW, Marrero D, Whiterock VJ, et al. Determination of 9-[2-phosphonylmethoxy)-ethyl]adenine in rat urine by high-performance liquid chromatography with fluorescence detection. J Chromatogr 1991; 572: 321-6
16. 16. Naesens L, Balzarini J, De Clercq E. Acyclic adenine nucleoside phosphonates in plasma determined by high-performance liquid chromatography with fluorescence detection. Clin Chem 1992; 38: 480-5
17. 17. Cundy KC, Barditch-Crovo P, Walker RE, et al. Clinical pharmacokinetics of adefovir in human immunodeficiency virus type 1-infected patients. Antimicrob Agents Chemother 1995; 39: 2401-5
18. 18. Naesens L, Balzarini J, De Clercq E. Pharmacokinetics in mice of the antiretrovirus agent 9-(2-phosphonylmethoxyethyl) adenine. Drug Metab Dispos 1992; 20: 747-52
19. 19. Cundy KC, Bidgood AM, Lynch G, et al. Pharmacokinetics, bioavailability, metabolism and tissue distribution of cidofovir (HPMPC) and cyclic HPMPC in rats. Drug Metab Dispos 1996; 24: 745-52
20. 20. Shaw J-P, Louie MS, Krishnamurthy K, et al. Pharmacokinetics and metabolism of selected prodrugs of PMEA in rats. Drug Metab Dispos 1997; 25: 362-6
21. 21. Cundy KC, Lynch G, Lee WA. Bioavailability and metabolism of cidofovir following topical administration to rabbits. Antiviral Res 1997; 35: 113-22
22. 22. Kern ER, Palmer J, Vogt PE, et al. Efficacy and pharmacokinetics of topical HPMPC in a genital herpes model [abstract]. Antiviral Res 1995; 26: A341
23. 23. Cundy KC, Marshburn J, Nakamura C, et al. Oral formulations of adefovir dipivoxil: in vitro dissolution and in vivo bioavailability in dogs. J Pharm Sci 1997; 86: 1334-8
24. 24. Cundy KC, Shaw J-P, Lee WA. Oral, subcutaneous and intramuscular bioavailabilities of the antiviral nucleotide analog 9-(2-phosphonyl-methoxyethyl)adenine in cynomolgus monkeys. Antimicrob Agents Chemother 1994; 38: 365-8
25. 25. Cundy KC, Li Z-H, Hitchcock MJM, et al. Pharmacokinetics of cidofovir in monkeys: evidence for a prolonged elimination phase representing phosphorylated drug. Drug Metab Dispos 1996; 24: 738-44
26. 26. Wachsman M, Petty BG, Cundy KC, et al. Pharmacokinetics, safety and bioavailability of cidofovir in HIV-infected subjects. Antiviral Res 1996; 29: 153-61
27. 27. Lalezari JP, Drew WL, Glutzer E, et al. HPMPC: results of a phase IlII study of a novel antiviral nucleotide analogue. J Infect Dis 1995; 171: 788-96
28. 28. Lalezari J, Holland G, Stagg R, et al. A randomized controlled study of cidofovir (CDV) for relapsing cytomegalovirus retinitis (CMV-R) in patients with AIDS [abstract]. Proceedings and Abstracts of the 35th Interscience Conference on Antimicrobial Agents and Chemotherapy; 1995 Sep 17-20: San Francisco
29. 29. Cundy KC, Li Z-H, Lee WA. Effect of probenecid on the distribution, metabolism and excretion of cidofovir in rabbits. Drug Metab Dispos 1996; 24: 315-21
30. 30. Balzarini J, Naesens L, Slachmuylders J, et al. 9-(2-Phosphonylmethoxyethy)adenine (PMEA) effectively inhibits retrovirus replication in vitro and simian immunodeficiency virus infection in rhesus monkeys. AIDS 1991; 5: 21-8
31. 31. Lacy SA, Hitchcock MJM, Lee WA, et al. Effect of oral probenecid coadministration on the chronic toxicity and pharmacokinetics of intravenous cidofovir in cynomolgus monkeys. Toxicol Sci 1997; 44: 97-106
32. 32. Dudley MN, Graham KK, Kaul S, et al. Pharmacokinetics of stavudine in patients with AIDS or AIDS-related complex. J Infect Dis 1992; 166: 480-5
33. 33. Gilead Sciences Inc. Vistide® package insert. Foster City (CA): Gilead Sciences Inc., 1998
34. 34. Sadler M, Morris-Jones S, Nelson M, et al. Successful treatment of cytomegalovirus encephalitis in an AIDS patient using cidofovir. AIDS 1997; 11: 1293-4
35. 35. Blick G, Garton T, Hopkins U, et al. Successful use of cidofovir in treating AIDS-related cytomegalovirus retinitis, encephalitis, and esophagitis. J Acquir Immune Defic Syndr Hum Retrovir 1997; 15: 84-5
36. 36. Cihlar T, Chen M. Identification of enzymes catalyzing two-step phosphorylation of cidofovir and the effect of cytomegalovirus infection on their activities in host cells. Mol Pharmacol 1996; 50: 1502-10
37. 37. Cihlar T, Votruba I, Horska K, et al. Metabolism of 1-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in human embryonic lung cells. Collect Czech Chem Commun 1992; 57: 661-72
38. 38. Merta A, Votruba I, Jindrich J, et al. Phosphorylation of 9-(2-phosphonylmethyoxyethyl)adenine and 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)adenine by AMP (dAMP) kinase from L1210 cells. Biochem Pharmacol 1992; 44: 2067-77
39. 39. Balzarini J, De Clercq E. 5-Phosphoribosyl-1-pyrophosphate synthetase converts the nucleotide phosphonates 9-(3-hydroxy-1-phosphonylmethoxypropyl)adenine and 9-(2-phosphonylmethoxyethyl)-adenine directly to their antivirally active diphosphate derivatives. J Biol Chem 1991; 266: 8686-9
40. 40. Fridland A. Cellular pharmacology of the antiviral agents PMPA and PMEA in vitro and in vivo [abstract]. 12th World AIDS Conference; 1998 Jun 28-Jul 3: Geneva
41. 41. Eisenberg EJ, Lynch GR, Bidgood AM, et al. Isolation and identification of a metabolite of cidofovir from rat kidney. J Pharm Biomed Anal 1998; 16: 1349-56
42. 42. Tune BM. Relationship between the transport and toxicity of cephalosporins in the kidney. J Infect Dis 1975; 132: 189-94
43. 43. Shaw J-P, Cundy KC. Biological screens of PMEA prodrugs. Pharm Res 1993; 10 (Suppl.): S294
44. 44. Starrett Jr JE, Tortolani DR, Russell J, et al. Synthesis, oral bioavailability determination, and in vitro evaluation of prodrugs of the antiviral agent 9-[2-(phosphonomethoxy)ethyl]-adenine (PMEA). J Med Chem 1994; 37: 1857-64
45. 45. Cundy KC, Fishback JA, Shaw J-P, et al. Oral bioavailability of the antiretroviral agent 9-(2-phosphonyl-methoxyethyl) adenine (PMEA) from three formulations of the prodrug bis(pivaloyloxymethyl)PMEA in fasted male cynomolgus monkeys. Pharm Res 1994; 11: 839-43
46. 46. Barditch-Crovo P, Cundy KC, Hellmann N, et al. Anti-HTV activity, safety and pharmacokinetics of adefovir dipivoxil (9-[2-(bispivaloyloxymethyl)phosphonyl-methoxyethyl]adenine) in HlV-infected patients. J Infect Dis 1996; 176: 406-13
47. 47. Gilson RJC, Murray-Lyon IM, Nelson MR, et al. Extended treatment with adefovir dipivoxil in patients with chronic hepatitis B virus infection [abstract]. 49th Annual Meeting of the American Association for the Study of Liver Disease; 1998 Nov 6-10: Chicago
48. 48. Aspe E, Guy RH, Lee WA, et al. Optimization of in vitro flux through hairless mouse skin of cidofovir, a potent nucleotide analog. J Pharm Sci 1995; 84: 750-4
49. 49. Gordon YZ, Naesens L, De Clercq E, et al. Treatment of adenoviral conjunctivitis with topical cidofovir [letter]. Cornea 1996; 15: 546
50. 14C-cidofovir in the rabbit [abstract]. Pharm Res 1997; 14 Suppl. 1; S-363
51. 51. Hosoya K, Lee VHL. Cidofovir transport in the pigmented rabbit conjunctiva. Curr Eye Res 1995; 119: 466-76
52. 52. Kirsch LS. Arevalo JF, De Clercq E, et al. Phase I/II study of intravitreal cidofovir for the treatment of cytomegalovirus retinitis in patients with the acquired immunodeficiency syndrome. Am J Ophthalmol 1995; 119: 466-76
53. 53. Cundy KC, Lynch G, Shaw J-P, et al. Distribution and metabolism of intravitreal cidofovir and cyclic HPMPC in rabbits. Curr Bye Res 1996; 15: 569-76
54. 54. Hitchcock MJM, Lacy SA, Lindsey JR, et al. The cyclic congener of cidofovir has reduced nephrotoxicity in three species [abstract]. Antiviral Res 1995; 26: A358
55. 55. Cunningham RF, Israili ZH, Dayton PG. Clinical pharmacokinetics of probenecid. Clin Pharmacokinet 1981; 6: 135-51
56. 56. Jacobs C, Kaubisch S, Halsey J, et al. The use of probenecid as a chemoprotector against cisplatin nephrotoxicity. Cancer 1991; 67: 1518-24
57. 57. Brody SR, Humphreys M, Gambertoglio JG, et al. An open label study of the pharmacokinetics of intravenous cidofovir in patients with varying degrees of renal insufficiency [abstract]. Clin Pharmacol Ther 1997; 61: 149
58. 58. Lush RM, Nguyen B-Y, Cundy KC, et al. The pharmacokinetics of 9-(2-phosphonyl-methoxyethyl)adenine (PMEA) and zidovudine (AZT) when administered in combination. J Appl Ther 1996; 1: 13-8
59. 59. Martin MA, Kane C. Nursing considerations in the use of cidofovir for CMV retinitis in patients with AIDS: report of a roundtable meeting. J Assoc Nurse AIDS Care 1997; 8: 66-74
60. 60. Lalezari JP. Cidofovir: a new therapy for cytomegalovirus retinitis. J Acquir Immune Defic Syndr Hum Retrovir 1997; 14 Suppl. 1: S22-6
61. 61. Lalezari JP, Kuppermann BD. Clinical experience with cidofovir in the treatment of cytomegalovirus retinitis. J Acquir Immune Defic Syndr Hum Retrovir 1997; 14 Suppl. 1: S27-31
62. 62. Palau LA, Tufty GT, Pankey GA. Recurrent iritis after intravenous administration of cidofovir. Clin Infect Dis 1997; 25: 337-8
63. 63. Kahn J, Lagakos S, Weng D, et al. Multi-center, randomized, double-blind placebo controlled study of the efficacy and safety of adefovir dipivoxil (ADV) when added to standard antiretroviral therapy (ART) [abstract]. 38th Annual Meeting of the Interscience Congress on Antimicrobial Agents and Chemotherapy; 1998 Sep 24-27: San Diego