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Chemical Compound Review

HIVID     4-amino-1-[(2R,5S)-5- (hydroxymethyl)oxolan...

Synonyms: Zalcitibine, ddCyd, zalcitabine, NSC-606170, NSC606170, ...
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Disease relevance of Dideoxycytidine


High impact information on Dideoxycytidine


Chemical compound and disease context of Dideoxycytidine


Biological context of Dideoxycytidine


Anatomical context of Dideoxycytidine

  • Similarly, treatment of rho 0 cell lines with ddC induced a reduction in mtDNA as well as h-mtTFA protein [15].
  • Uridine fully abrogated the adverse effects of zalcitabine on hepatocyte proliferation and normalized lactate synthesis, intracellular lipids and COX II levels by adjusting mtDNA levels to about 65% of NRTI-unexposed control cells [12].
  • Zalcitabine induced a dose dependent microvesicular steatohepatitis with abundant mitochondria [13].
  • Stavudine and zidovudine increased mitochondrial mass by two to fourfold, and lowered the mitochondrial membrane potential (JC-1 stain) as did zalcitabine (0.2 microM) [16].
  • The decrease of mtDNA content caused by ddC also occurred in nerve growth factor-treated PC12 cells, which differentiate to neuron-like cells upon treatment with nerve growth factor [17].

Associations of Dideoxycytidine with other chemical compounds


Gene context of Dideoxycytidine

  • Unexpectedly, alpha-dideoxycytidine (ddC) was a 3-fold better substrate for dCK than beta-ddC [23].
  • In contrast, ddC alone and combined AZT/ddC decreased the CD25 molecules in a marked and dose-dependent manner [24].
  • These results demonstrate that long-term treatment of H9 cells in the presence of ddC down-regulated TK1 and TK2 gene expression and reduced the expression and activity of TK in the resistant cells [25].
  • Similar effects are observed by knocking down DNA polymerase-beta or by using dideoxycytidine, a preferential inhibitor of this enzyme [26].
  • Circulating p24 antigen levels and responses to dideoxycytidine in human immunodeficiency virus (HIV) infections. A phase I and II study [27].

Analytical, diagnostic and therapeutic context of Dideoxycytidine


  1. Treatment of human immunodeficiency virus infection with saquinavir, zidovudine, and zalcitabine. AIDS Clinical Trials Group. Collier, A.C., Coombs, R.W., Schoenfeld, D.A., Bassett, R.L., Timpone, J., Baruch, A., Jones, M., Facey, K., Whitacre, C., McAuliffe, V.J., Friedman, H.M., Merigan, T.C., Reichman, R.C., Hooper, C., Corey, L. N. Engl. J. Med. (1996) [Pubmed]
  2. A comparative trial of didanosine or zalcitabine after treatment with zidovudine in patients with human immunodeficiency virus infection. The Terry Beirn Community Programs for Clinical Research on AIDS. Abrams, D.I., Goldman, A.I., Launer, C., Korvick, J.A., Neaton, J.D., Crane, L.R., Grodesky, M., Wakefield, S., Muth, K., Kornegay, S. N. Engl. J. Med. (1994) [Pubmed]
  3. Inhibition of duck hepatitis B virus replication by 2',3'-dideoxycytidine. A potent inhibitor of reverse transcriptase. Kassianides, C., Hoofnagle, J.H., Miller, R.H., Doo, E., Ford, H., Broder, S., Mitsuya, H. Gastroenterology (1989) [Pubmed]
  4. Hypersensitivity syndrome associated with zalcitabine therapy. Tancrède-Bohin, E., Grange, F., Bournerias, I., Roujeau, J.C., Guillaume, J.C. Lancet (1996) [Pubmed]
  5. Zalcitabine compared with zidovudine in patients with advanced HIV-1 infection who received previous zidovudine therapy. Fischl, M.A., Olson, R.M., Follansbee, S.E., Lalezari, J.P., Henry, D.H., Frame, P.T., Remick, S.C., Salgo, M.P., Lin, A.H., Nauss-Karol, C., Lieberman, J., Soo, W. Ann. Intern. Med. (1993) [Pubmed]
  6. Resistance to 1-beta-D-arabinofuranosylcytosine in human T-lymphoblasts mediated by mutations within the deoxycytidine kinase gene. Owens, J.K., Shewach, D.S., Ullman, B., Mitchell, B.S. Cancer Res. (1992) [Pubmed]
  7. Acetyl-carnitine deficiency in AIDS patients with neurotoxicity on treatment with antiretroviral nucleoside analogues. Famularo, G., Moretti, S., Marcellini, S., Trinchieri, V., Tzantzoglou, S., Santini, G., Longo, A., De Simone, C. AIDS (1997) [Pubmed]
  8. Susceptibility of human T cell leukemia virus type 1 to reverse-transcriptase inhibitors: evidence for resistance to lamivudine. García-Lerma, J.G., Nidtha, S., Heneine, W. J. Infect. Dis. (2001) [Pubmed]
  9. Pharmacokinetics and distribution over the blood-brain barrier of zalcitabine (2',3'-dideoxycytidine) and BEA005 (2', 3'-dideoxy-3'-hydroxymethylcytidine) in rats, studied by microdialysis. Borg, N., Ståhle, L. Antimicrob. Agents Chemother. (1998) [Pubmed]
  10. Comparison between rules-based human immunodeficiency virus type 1 genotype interpretations and real or virtual phenotype: concordance analysis and correlation with clinical outcome in heavily treated patients. Torti, C., Quiros-Roldan, E., Keulen, W., Scudeller, L., Lo Caputo, S., Boucher, C., Castelli, F., Mazzotta, F., Pierotti, P., Been-Tiktak, A.M., Buccoliero, G., De Gennaro, M., Carosi, G., Tinelli, C. J. Infect. Dis. (2003) [Pubmed]
  11. Safety and activity of zalcitabine and zidovudine combination in HIV-positive people with CD4 cell counts < or = 300 cells/mm3. The Roche M50002 Study Group. Moyle, G.J., Walker, M., Harris, R., Kellagher, A., Warburg, M. Antivir. Ther. (Lond.) (1996) [Pubmed]
  12. Uridine abrogates mitochondrial toxicity related to nucleoside analogue reverse transcriptase inhibitors in HepG2 cells. Walker, U.A., Venhoff, N., Koch, E.C., Olschewski, M., Schneider, J., Setzer, B. Antivir. Ther. (Lond.) (2003) [Pubmed]
  13. Uridine supplementation antagonizes zalcitabine-induced microvesicular steatohepatitis in mice. Lebrecht, D., Vargas-Infante, Y.A., Setzer, B., Kirschner, J., Walker, U.A. Hepatology (2007) [Pubmed]
  14. Transdermal delivery of zalcitabine: in vitro skin permeation study. Kim, D.D., Chien, Y.W. AIDS (1995) [Pubmed]
  15. Deficiency of the human mitochondrial transcription factor h-mtTFA in infantile mitochondrial myopathy is associated with mtDNA depletion. Poulton, J., Morten, K., Freeman-Emmerson, C., Potter, C., Sewry, C., Dubowitz, V., Kidd, H., Stephenson, J., Whitehouse, W., Hansen, F.J. Hum. Mol. Genet. (1994) [Pubmed]
  16. The HIV-1 nucleoside reverse transcriptase inhibitors stavudine and zidovudine alter adipocyte functions in vitro. Caron, M., Auclair, M., Lagathu, C., Lombès, A., Walker, U.A., Kornprobst, M., Capeau, J. AIDS (2004) [Pubmed]
  17. Effect of anti-human immunodeficiency virus nucleoside analogs on mitochondrial DNA and its implication for delayed toxicity. Chen, C.H., Vazquez-Padua, M., Cheng, Y.C. Mol. Pharmacol. (1991) [Pubmed]
  18. Health status and function with zidovudine or zalcitabine as initial therapy for AIDS. A randomized controlled trial. Roche 3300/ACTG 114 Study Group. Bozzette, S.A., Kanouse, D.E., Berry, S., Duan, N. JAMA (1995) [Pubmed]
  19. Quality of life outcomes of saquinavir, zalcitabine and combination saquinavir plus zalcitabine therapy for adults with advanced HIV infection with CD4 counts between 50 and 300 cells/mm3. Revicki, D.A., Swartz, C., Wu, A.W., Haubrich, R., Collier, A.C. Antivir. Ther. (Lond.) (1999) [Pubmed]
  20. Muscle and liver lactate metabolism in HAART-treated and naive HIV-infected patients: the MITOVIR study. Ghosn, J., Guiguet, M., Jardel, C., Benyaou, R., Zeller, V., Simon, A., Valantin, M.A., Amellal, B., Assoumo, L., Hogrel, J.Y., Costagliola, D., Katlama, C., Lombès, A. Antivir. Ther. (Lond.) (2005) [Pubmed]
  21. Neurological outcomes in late HIV infection: adverse impact of neurological impairment on survival and protective effect of antiviral therapy. AIDS Clinical Trial Group and Neurological AIDS Research Consortium study team. Price, R.W., Yiannoutsos, C.T., Clifford, D.B., Zaborski, L., Tselis, A., Sidtis, J.J., Cohen, B., Hall, C.D., Erice, A., Henry, K. AIDS (1999) [Pubmed]
  22. Solid-phase extraction combined with radioimmunoassay for measurement of zalcitabine (2',3'-dideoxycytidine) in plasma and serum. Roberts, W.L., Buckley, T.J., Rainey, P.M., Jatlow, P.I. Clin. Chem. (1994) [Pubmed]
  23. Stereoisomeric selectivity of human deoxyribonucleoside kinases. Wang, J., Choudhury, D., Chattopadhyaya, J., Eriksson, S. Biochemistry (1999) [Pubmed]
  24. Down-regulation of interleukin-2 receptor gene activation and protein expression by dideoxynucleoside analogs. Viora, M., Camponeschi, B. Cell. Immunol. (1995) [Pubmed]
  25. 2', 3'-Dideoxycytidine represses thymidine kinases 1 and 2 expression in T-lymphoid cells. Han, T., Fernandez, M., Sarkar, M., Agarwal, R.P. Life Sci. (2004) [Pubmed]
  26. Erratic expression of DNA polymerases by beta-amyloid causes neuronal death. Copani, A., Sortino, M.A., Caricasole, A., Chiechio, S., Chisari, M., Battaglia, G., Giuffrida-Stella, A.M., Vancheri, C., Nicoletti, F. FASEB J. (2002) [Pubmed]
  27. Circulating p24 antigen levels and responses to dideoxycytidine in human immunodeficiency virus (HIV) infections. A phase I and II study. Merigan, T.C., Skowron, G., Bozzette, S.A., Richman, D., Uttamchandani, R., Fischl, M., Schooley, R., Hirsch, M., Soo, W., Pettinelli, C. Ann. Intern. Med. (1989) [Pubmed]
  28. Antiretroviral therapy for adult HIV-infected patients. Recommendations from a state-of-the-art conference. National Institute of Allergy and Infectious Diseases State-of-the-Art Panel on Anti-Retroviral Therapy for Adult HIV-Infected Patients. Sande, M.A., Carpenter, C.C., Cobbs, C.G., Holmes, K.K., Sanford, J.P. JAMA (1993) [Pubmed]
  29. Finding a role for zalcitabine in the HAART era. Moyle, G.J., Gazzard, B.G. Antivir. Ther. (Lond.) (1998) [Pubmed]
  30. Application of a radioimmunoassay for determination of levels of zalcitabine (ddC) in human plasma, urine, and cerebrospinal fluid. Burger, D.M., Rosing, H., ten Napel, C.H., Duyts, T., Meenhorst, P.L., Mulder, J.W., Koks, C.H., Bult, A., Beijnen, J.H. Antimicrob. Agents Chemother. (1994) [Pubmed]
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