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Chemical Compound Review

azithromycin     (4R,5R,14R)-11-(4- dimethylamino-3-hydroxy...

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Disease relevance of azithromycin


Psychiatry related information on azithromycin


High impact information on azithromycin


Chemical compound and disease context of azithromycin


Biological context of azithromycin

  • We report an uncontrolled phase I study in which male homosexuals with AIDS and M avium complex disease were given 500 mg azithromycin per day orally for 10, 20, or 30 days [18].
  • For patients treated with azithromycin, development of an antibody response increased the possibility of achieving a complete response (81% of seropositive patients achieved a complete response compared with 60% of seronegative patients; P=0.043) [14].
  • The pharmacokinetics of azithromycin, the first azalide, are characterized by a rapid and extensive movement of the drug from the serum into intracellular compartments [19].
  • More importantly, azithromycin has high tissue bioavailability and a tissue half-life of between 2 and 4 days [20].
  • These kinetics allow azithromycin to be administered once daily [19].

Anatomical context of azithromycin


Associations of azithromycin with other chemical compounds

  • Although nanomolar concentrations of azithromycin and clindamycin prevent replication of T. gondii in both cell culture and in vivo assays, no inhibition of protein labeling was observed in either extracellular or intracellular parasites treated with up to 100 microM drug for up to 24 h [24].
  • We investigated the ability of azithromycin to prevent malaria in volunteers infected with a chloroquine-resistant strain of Plasmodium falciparum [25].
  • This was a randomized, third-party-blinded, multicenter study that compared once-daily azithromycin (500 mg on day 1, followed by 250 mg on days 2-5) to cefaclor (500 mg three times daily for 10 days) in the treatment of patients with acute bronchitis or pneumonia [17].
  • A double-blind placebo-controlled study was conducted in healthy men to determine the effect of coadministration of azithromycin on the pharmacodynamics and pharmacokinetics of terfenadine [26].
  • Pretreatment of J774 mouse macrophages by the dicationic macrolide antibiotic, azithromycin (AZ), selectively inhibited fluid-phase endocytosis of horseradish peroxidase and lucifer yellow, but not phagocytosis of latex beads [23].

Gene context of azithromycin


Analytical, diagnostic and therapeutic context of azithromycin

  • Azithromycin for empirical treatment of the nongonococcal urethritis syndrome in men. A randomized double-blind study [13].
  • Azithromycin (a macrolide-like antibiotic) has antimalarial effects in vitro and in animal models [32].
  • The new azalide antibiotic azithromycin is effective as a single oral dose in the chemotherapy of genital Chlamydia trachomatis infections, and we have assessed its efficacy for trachoma treatment [33].
  • INTERPRETATION: Prophylaxis with azithromycin did not affect the likelihood that a woman would retain her IUD at 90 days or the frequency of postinsertion medical attention [34].
  • SETTING: Clinical trials center of Walter Reed Army Institute of Research, Washington, D.C. PATIENTS: Each of the two cohorts consisted of 12 normal adult volunteers who had not had malaria during the previous 2 years: 10 who received azithromycin prophylaxis and 2 controls who did not received treatment [35].


  1. Prophylaxis against disseminated Mycobacterium avium complex with weekly azithromycin, daily rifabutin, or both. California Collaborative Treatment Group. Havlir, D.V., Dubé, M.P., Sattler, F.R., Forthal, D.N., Kemper, C.A., Dunne, M.W., Parenti, D.M., Lavelle, J.P., White, A.C., Witt, M.D., Bozzette, S.A., McCutchan, J.A. N. Engl. J. Med. (1996) [Pubmed]
  2. Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Tu, D., Blaha, G., Moore, P.B., Steitz, T.A. Cell (2005) [Pubmed]
  3. A controlled trial of a single dose of azithromycin for the treatment of chlamydial urethritis and cervicitis. The Azithromycin for Chlamydial Infections Study Group. Martin, D.H., Mroczkowski, T.F., Dalu, Z.A., McCarty, J., Jones, R.B., Hopkins, S.J., Johnson, R.B. N. Engl. J. Med. (1992) [Pubmed]
  4. Atovaquone and azithromycin for the treatment of babesiosis. Krause, P.J., Lepore, T., Sikand, V.K., Gadbaw, J., Burke, G., Telford, S.R., Brassard, P., Pearl, D., Azlanzadeh, J., Christianson, D., McGrath, D., Spielman, A. N. Engl. J. Med. (2000) [Pubmed]
  5. Treatment of presumed cerebral toxoplasmosis with azithromycin. Godofsky, E.W. N. Engl. J. Med. (1994) [Pubmed]
  6. Toxic catatonia secondary to azithromycin. Plana, M.T., Blanch, J., Romero, S., Serra, M., Gasto, C. The Journal of clinical psychiatry. (2006) [Pubmed]
  7. Economic analysis of antibiotic regimens used in the treatment pharyngitis: a prospective comparison of azithromycin versus roxithromycin. Carbon, C., Hotton, J.M., Pépin, L.F., Wohlhuter, C., Souêtre, E., Hardens, M., Lozet, H., Riviera, M. J. Antimicrob. Chemother. (1996) [Pubmed]
  8. Erythema migrans: comparison of treatment with azithromycin, doxycycline and phenoxymethylpenicillin. Strle, F., Ruzic, E., Cimperman, J. J. Antimicrob. Chemother. (1992) [Pubmed]
  9. Doxycycline and azithromycin for prevention of chlamydial persistence or recurrence one month after treatment in women. A use-effectiveness study in public health settings. Hillis, S.D., Coles, F.B., Litchfield, B., Black, C.M., Mojica, B., Schmitt, K., St Louis, M.E. Sexually transmitted diseases. (1998) [Pubmed]
  10. Defining the optimum treatment regimen for azithromycin in acute tonsillopharyngitis. Cohen, R. Pediatr. Infect. Dis. J. (2004) [Pubmed]
  11. Discontinuation of prophylaxis for Mycobacterium avium complex disease in HIV-infected patients who have a response to antiretroviral therapy. Terry Beirn Community Programs for Clinical Research on AIDS. El-Sadr, W.M., Burman, W.J., Grant, L.B., Matts, J.P., Hafner, R., Crane, L., Zeh, D., Gallagher, B., Mannheimer, S.B., Martinez, A., Gordin, F. N. Engl. J. Med. (2000) [Pubmed]
  12. Predictors of broad-spectrum antibiotic prescribing for acute respiratory tract infections in adult primary care. Steinman, M.A., Landefeld, C.S., Gonzales, R. JAMA (2003) [Pubmed]
  13. Azithromycin for empirical treatment of the nongonococcal urethritis syndrome in men. A randomized double-blind study. Stamm, W.E., Hicks, C.B., Martin, D.H., Leone, P., Hook, E.W., Cooper, R.H., Cohen, M.S., Batteiger, B.E., Workowski, K., McCormack, W.M. JAMA (1995) [Pubmed]
  14. Azithromycin compared with amoxicillin in the treatment of erythema migrans. A double-blind, randomized, controlled trial. Luft, B.J., Dattwyler, R.J., Johnson, R.C., Luger, S.W., Bosler, E.M., Rahn, D.W., Masters, E.J., Grunwaldt, E., Gadgil, S.D. Ann. Intern. Med. (1996) [Pubmed]
  15. Propionibacterium acnes isolated from synovial tissue and fluid in a patient with oligoarthritis associated with acne and pustulosis. Schaeverbeke, T., Lequen, L., de Barbeyrac, B., Labbé, L., Bébéar, C.M., Morrier, Y., Bannwarth, B., Bébéar, C., Dehais, J. Arthritis Rheum. (1998) [Pubmed]
  16. Impact of clarithromycin and azithromycin on patterns of treatment and survival among AIDS patients with disseminated Mycobacterium avium complex. Ives, D.V., Davis, R.B., Currier, J.S. AIDS (1995) [Pubmed]
  17. Multicenter evaluation of azithromycin and cefaclor in acute lower respiratory tract infections. Dark, D. Am. J. Med. (1991) [Pubmed]
  18. Azithromycin for treatment of Mycobacterium avium-intracellulare complex infection in patients with AIDS. Young, L.S., Wiviott, L., Wu, M., Kolonoski, P., Bolan, R., Inderlied, C.B. Lancet (1991) [Pubmed]
  19. Tissue-directed pharmacokinetics. Schentag, J.J., Ballow, C.H. Am. J. Med. (1991) [Pubmed]
  20. Azithromycin in the treatment of uncomplicated genital chlamydial infections. Stamm, W.E. Am. J. Med. (1991) [Pubmed]
  21. Randomized secondary prevention trial of azithromycin in patients with coronary artery disease and serological evidence for Chlamydia pneumoniae infection: The Azithromycin in Coronary Artery Disease: Elimination of Myocardial Infection with Chlamydia (ACADEMIC) study. Anderson, J.L., Muhlestein, J.B., Carlquist, J., Allen, A., Trehan, S., Nielson, C., Hall, S., Brady, J., Egger, M., Horne, B., Lim, T. Circulation (1999) [Pubmed]
  22. Azithromycin blocks neutrophil recruitment in Pseudomonas endobronchial infection. Tsai, W.C., Rodriguez, M.L., Young, K.S., Deng, J.C., Thannickal, V.J., Tateda, K., Hershenson, M.B., Standiford, T.J. Am. J. Respir. Crit. Care Med. (2004) [Pubmed]
  23. Azithromycin, a lysosomotropic antibiotic, has distinct effects on fluid-phase and receptor-mediated endocytosis, but does not impair phagocytosis in J774 macrophages. Tyteca, D., Van Der Smissen, P., Mettlen, M., Van Bambeke, F., Tulkens, P.M., Mingeot-Leclercq, M.P., Courtoy, P.J. Exp. Cell Res. (2002) [Pubmed]
  24. Inhibition of cytoplasmic and organellar protein synthesis in Toxoplasma gondii. Implications for the target of macrolide antibiotics. Beckers, C.J., Roos, D.S., Donald, R.G., Luft, B.J., Schwab, J.C., Cao, Y., Joiner, K.A. J. Clin. Invest. (1995) [Pubmed]
  25. Azithromycin prophylaxis against a chloroquine-resistant strain of Plasmodium falciparum. Kuschner, R.A., Heppner, D.G., Andersen, S.L., Wellde, B.T., Hall, T., Schneider, I., Ballou, W.R., Foulds, G., Sadoff, J.C., Schuster, B. Lancet (1994) [Pubmed]
  26. Azithromycin and terfenadine: lack of drug interaction. Harris, S., Hilligoss, D.M., Colangelo, P.M., Eller, M., Okerholm, R. Clin. Pharmacol. Ther. (1995) [Pubmed]
  27. Azithromycin inhibits MUC5AC production induced by the Pseudomonas aeruginosa autoinducer N-(3-Oxododecanoyl) homoserine lactone in NCI-H292 Cells. Imamura, Y., Yanagihara, K., Mizuta, Y., Seki, M., Ohno, H., Higashiyama, Y., Miyazaki, Y., Tsukamoto, K., Hirakata, Y., Tomono, K., Kadota, J., Kohno, S. Antimicrob. Agents Chemother. (2004) [Pubmed]
  28. Modulation of tissue factor expression by rapamycin and FK-506 in lipopolysaccharide-stimulated human mononuclear cells and serum-stimulated aortic smooth muscle cells. Ollivier, V., Hammal, S., Ameziane, N., Labro, M.T., de Prost, D. Thromb. Haemost. (2005) [Pubmed]
  29. Moxifloxacin but not ciprofloxacin or azithromycin selectively inhibits IL-8, IL-6, ERK1/2, JNK, and NF-{kappa}B activation in a cystic fibrosis epithelial cell line. Blau, H., Klein, K., Shalit, I., Halperin, D., Fabian, I. Am. J. Physiol. Lung Cell Mol. Physiol. (2007) [Pubmed]
  30. Azithromycin reduces spontaneous and induced inflammation in DeltaF508 cystic fibrosis mice. Legssyer, R., Huaux, F., Lebacq, J., Delos, M., Marbaix, E., Lebecque, P., Lison, D., Scholte, B.J., Wallemacq, P., Leal, T. Respir. Res. (2006) [Pubmed]
  31. The ACADEMIC study in perspective (Azithromycin in coronary artery disease: elimination of myocardial infection with Chlamydia). Anderson, J.L., Muhlestein, J.B. J. Infect. Dis. (2000) [Pubmed]
  32. Effects of azithromycin on malariometric indices in The Gambia. Sadiq, S.T., Glasgow, K.W., Drakeley, C.J., Muller, O., Greenwood, B.M., Mabey, D.C., Bailey, R.L. Lancet (1995) [Pubmed]
  33. Randomised controlled trial of single-dose azithromycin in treatment of trachoma. Bailey, R.L., Arullendran, P., Whittle, H.C., Mabey, D.C. Lancet (1993) [Pubmed]
  34. Randomised controlled trial of prophylactic antibiotics before insertion of intrauterine devices. IUD Study Group. Walsh, T., Grimes, D., Frezieres, R., Nelson, A., Bernstein, L., Coulson, A., Bernstein, G. Lancet (1998) [Pubmed]
  35. Prophylaxis of Plasmodium falciparum malaria with azithromycin administered to volunteers. Anderson, S.L., Berman, J., Kuschner, R., Wesche, D., Magill, A., Wellde, B., Schneider, I., Dunne, M., Schuster, B.G. Ann. Intern. Med. (1995) [Pubmed]
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