The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Miambutol     (2S)-2-[2-[[(2S)-1- hydroxybutan-2...

Synonyms: Purderal, Etambutol, Etapiam, Myambutol, Mycobutol, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of ethambutol


Psychiatry related information on ethambutol


High impact information on ethambutol

  • Ethambutol (EMB), a frontline antituberculous drug, targets the mycobacterial cell wall, a unique structure among prokaryotes which consists of an outer layer of mycolic acids covalently bound to peptidoglycan via the arabinogalactan [2].
  • Specific inhibition of spermidine synthase from mycobacteria by ethambutol [8].
  • Patients with bacteriologically positive pulmonary tuberculosis were treated initially for an average of three and a half months with isoniazid, rifampicin, and ethambutol and then a total of one year's treatment was completed with either rifampicin plus isoniazid (R+I) or with ethambutol plus isoniazid (E+I) [9].
  • Isoniazid and ethambutol absorption with jejunoileal bypass [10].
  • The Rv3806c gene encoding 5-phospho-alpha-d-ribose-1-diphosphate:decaprenyl-phosphate 5-phosphoribosyltransferase is known to be essential for the growth of M. tuberculosis, and the tuberculosis drug ethambutol inhibits other steps in arabinan biosynthesis [11].

Chemical compound and disease context of ethambutol


Biological context of ethambutol


Anatomical context of ethambutol


Associations of ethambutol with other chemical compounds

  • Two clinical isolates of the same strain, numbers 397 and 417, were obtained from an AIDS patient with disseminated M. avium complex infection before and after treatment with a regimen of clarithromycin and ethambutol [25].
  • Among 430 patients treated between 1990 and 1999, the incidence of all major adverse effects was 1.48 per 100 person-months of exposure (95% confidence interval [95% CI], 1.31 to 1.61) for pyrazinamide, compared with 0.49 (95% CI, 0.42 to 0.55) for isoniazid, 0.43 (95% CI, 0.37 to 0.49) for rifampin, and 0.07 (95% CI, 0.04 to 0.10) for ethambutol [26].
  • OBJECTIVE: To compare the impact of moxifloxacin versus ethambutol, both in combination with isoniazid, rifampin, and pyrazinamide, on sputum culture conversion at 2 mo as a measure of the potential sterilizing activity of alternate induction regimens [12].
  • Compared with controls, sparfloxacin or ethambutol decreased the CFU counts in spleens and lungs (P < 0.001) [16].
  • Enterococcal strains resistant to vancomycin (VanA, VanB, and VanC resistance phenotypes), pneumococcal strains resistant to penicillin, and M. tuberculosis strains resistant to common antitubercular agents (isoniazid, streptomycin, rifampin, ethionamide, and ethambutol) were not cross-resistant to the oxazolidinones [27].

Gene context of ethambutol


Analytical, diagnostic and therapeutic context of ethambutol

  • Cure was achieved by debridement and chemotherapy with ethambutol and rifampin [33].
  • An animal model was developed for studying macrolide-resistant Mycobacterium avium complex (MAC) and to measure the effect of ethambutol on resistance [34].
  • Titration of amoxicillin-clavulanic acid with a fixed 2-micrograms/ml concentration of ethambutol resulted in synergistic activity against 3 of 9 isolates of M. fortuitum, 10 of 10 isolates of M. kansasii, and 5 of 5 isolates of M. marinum [35].
  • Substitution of the new diamine antibiotic SQ109 for ethambutol in a mouse model of chronic tuberculosis (TB) improved efficacy of combination drug therapy with first-line TB drugs rifampin and isoniazid, with or without pyrazinamide: at 8 weeks, lung bacteria were 1.5 log(10) lower in SQ109-containing regimens [36].
  • In vivo oral administration of SQ109 (0.1-25 mg kg(-1) day(-1)) to the mice for 28 days resulted in dose-dependent reductions of mycobacterial load in both spleen and lung comparable to that of EMB administered at 100 mg kg(-1) day(-1), but was less potent than INH at 25 mg kg(-1) day(-1) [37].


  1. A comparison of two regimens for the treatment of Mycobacterium avium complex bacteremia in AIDS: rifabutin, ethambutol, and clarithromycin versus rifampin, ethambutol, clofazimine, and ciprofloxacin. Canadian HIV Trials Network Protocol 010 Study Group. Shafran, S.D., Singer, J., Zarowny, D.P., Phillips, P., Salit, I., Walmsley, S.L., Fong, I.W., Gill, M.J., Rachlis, A.R., Lalonde, R.G., Fanning, M.M., Tsoukas, C.M. N. Engl. J. Med. (1996) [Pubmed]
  2. The emb operon, a gene cluster of Mycobacterium tuberculosis involved in resistance to ethambutol. Telenti, A., Philipp, W.J., Sreevatsan, S., Bernasconi, C., Stockbauer, K.E., Wieles, B., Musser, J.M., Jacobs, W.R. Nat. Med. (1997) [Pubmed]
  3. Hydroxycobalamin for ethambutol-induced optic neuropathy. Guerra, R., Casu, L. Lancet (1981) [Pubmed]
  4. Identification of a novel arabinofuranosyltransferase (AftA) involved in cell wall arabinan biosynthesis in Mycobacterium tuberculosis. Alderwick, L.J., Seidel, M., Sahm, H., Besra, G.S., Eggeling, L. J. Biol. Chem. (2006) [Pubmed]
  5. Rapid-onset reversible ocular toxicity from ethambutol therapy. Schild, H.S., Fox, B.C. Am. J. Med. (1991) [Pubmed]
  6. Ocular adverse effects associated with systemic medications : recognition and management. Santaella, R.M., Fraunfelder, F.W. Drugs (2007) [Pubmed]
  7. Pharmacokinetic interaction between rifampicin and the once-daily combination of saquinavir and low-dose ritonavir in HIV-infected patients with tuberculosis. Ribera, E., Azuaje, C., Lopez, R.M., Domingo, P., Curran, A., Feijoo, M., Pou, L., Sánchez, P., Sambeat, M.A., Colomer, J., Lopez-Colomes, J.L., Crespo, M., Falcó, V., Ocaña, I., Pahissa, A. J. Antimicrob. Chemother. (2007) [Pubmed]
  8. Specific inhibition of spermidine synthase from mycobacteria by ethambutol. Pöso, H., Paulin, L., Brander, E. Lancet (1983) [Pubmed]
  9. Ethambutol plus isoniazid compared with rifampicin plus isoniazid in antituberculosis continuation treatment. Lees, A.W., Allan, G.W., Smith, J., Tyrrell, W.F. Lancet (1977) [Pubmed]
  10. Isoniazid and ethambutol absorption with jejunoileal bypass. Polk, R.E., Tenenbaum, M., Kline, B. Ann. Intern. Med. (1978) [Pubmed]
  11. Identification and active expression of the Mycobacterium tuberculosis gene encoding 5-phospho-{alpha}-d-ribose-1-diphosphate: decaprenyl-phosphate 5-phosphoribosyltransferase, the first enzyme committed to decaprenylphosphoryl-d-arabinose synthesis. Huang, H., Scherman, M.S., D'Haeze, W., Vereecke, D., Holsters, M., Crick, D.C., McNeil, M.R. J. Biol. Chem. (2005) [Pubmed]
  12. Moxifloxacin versus ethambutol in the first 2 months of treatment for pulmonary tuberculosis. Burman, W.J., Goldberg, S., Johnson, J.L., Muzanye, G., Engle, M., Mosher, A.W., Choudhri, S., Daley, C.L., Munsiff, S.S., Zhao, Z., Vernon, A., Chaisson, R.E. Am. J. Respir. Crit. Care Med. (2006) [Pubmed]
  13. Low levels of pyrazinamide and ethambutol in children with tuberculosis and impact of age, nutritional status, and human immunodeficiency virus infection. Graham, S.M., Bell, D.J., Nyirongo, S., Hartkoorn, R., Ward, S.A., Molyneux, E.M. Antimicrob. Agents Chemother. (2006) [Pubmed]
  14. Postantibiotic effect of clarithromycin alone and combined with ethambutol against Mycobacterium avium complex. Ellis, L.C., Benson, C.A., Koenig, G.I., Trenholme, G.M. Antimicrob. Agents Chemother. (1995) [Pubmed]
  15. Randomized, placebo-controlled trial of rifampin, ethambutol, and ciprofloxacin for AIDS patients with disseminated Mycobacterium avium complex infection. Jacobson, M.A., Yajko, D., Northfelt, D., Charlebois, E., Gary, D., Brosgart, C., Sanders, C.A., Hadley, W.K. J. Infect. Dis. (1993) [Pubmed]
  16. Sparfloxacin, ethambutol, and cortisol receptor inhibitor RU-40 555 treatment for disseminated Mycobacterium avium complex infection of normal C57BL/6 mice. Perronne, C., Cohen, Y., Truffot-Pernot, C., Grosset, J., Vildé, J.L., Pocidalo, J.J. Antimicrob. Agents Chemother. (1992) [Pubmed]
  17. Deletion of Cg-emb in corynebacterianeae leads to a novel truncated cell wall arabinogalactan, whereas inactivation of Cg-ubiA results in an arabinan-deficient mutant with a cell wall galactan core. Alderwick, L.J., Radmacher, E., Seidel, M., Gande, R., Hitchen, P.G., Morris, H.R., Dell, A., Sahm, H., Eggeling, L., Besra, G.S. J. Biol. Chem. (2005) [Pubmed]
  18. Bacterial FHA domains: neglected players in the phospho-threonine signalling game? Pallen, M., Chaudhuri, R., Khan, A. Trends Microbiol. (2002) [Pubmed]
  19. Kinetics of oral ethambutol in the normal subject. Lee, C.S., Gambertoglio, J.G., Brater, D.C., Benet, L.Z. Clin. Pharmacol. Ther. (1977) [Pubmed]
  20. Role of embB codon 306 mutations in Mycobacterium tuberculosis revisited: a novel association with broad drug resistance and IS6110 clustering rather than ethambutol resistance. Hazbón, M.H., Bobadilla del Valle, M., Guerrero, M.I., Varma-Basil, M., Filliol, I., Cavatore, M., Colangeli, R., Safi, H., Billman-Jacobe, H., Lavender, C., Fyfe, J., García-García, L., Davidow, A., Brimacombe, M., León, C.I., Porras, T., Bose, M., Chaves, F., Eisenach, K.D., Sifuentes-Osornio, J., Ponce de León, A., Cave, M.D., Alland, D. Antimicrob. Agents Chemother. (2005) [Pubmed]
  21. Visual evoked potentials in the detection of subclinical optic toxic effects secondary to ethambutol. Yiannikas, C., Walsh, J.C., McLeod, J.G. Arch. Neurol. (1983) [Pubmed]
  22. Antibiotic uptake by alveolar macrophages of smokers. Hand, W.L., Boozer, R.M., King-Thompson, N.L. Antimicrob. Agents Chemother. (1985) [Pubmed]
  23. Ethambutol is toxic to retinal ganglion cells via an excitotoxic pathway. Heng, J.E., Vorwerk, C.K., Lessell, E., Zurakowski, D., Levin, L.A., Dreyer, E.B. Invest. Ophthalmol. Vis. Sci. (1999) [Pubmed]
  24. In vivo activities of newer rifamycin analogs against Mycobacterium avium infection. Klemens, S.P., Cynamon, M.H. Antimicrob. Agents Chemother. (1991) [Pubmed]
  25. Altered expression profile of the surface glycopeptidolipids in drug-resistant clinical isolates of Mycobacterium avium complex. Khoo, K.H., Jarboe, E., Barker, A., Torrelles, J., Kuo, C.W., Chatterjee, D. J. Biol. Chem. (1999) [Pubmed]
  26. Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Yee, D., Valiquette, C., Pelletier, M., Parisien, I., Rocher, I., Menzies, D. Am. J. Respir. Crit. Care Med. (2003) [Pubmed]
  27. In vitro activities of U-100592 and U-100766, novel oxazolidinone antibacterial agents. Zurenko, G.E., Yagi, B.H., Schaadt, R.D., Allison, J.W., Kilburn, J.O., Glickman, S.E., Hutchinson, D.K., Barbachyn, M.R., Brickner, S.J. Antimicrob. Agents Chemother. (1996) [Pubmed]
  28. Deletion of the Mycobacterium tuberculosis pknH gene confers a higher bacillary load during the chronic phase of infection in BALB/c mice. Papavinasasundaram, K.G., Chan, B., Chung, J.H., Colston, M.J., Davis, E.O., Av-Gay, Y. J. Bacteriol. (2005) [Pubmed]
  29. Multidrug resistance following expression of the Escherichia coli marA gene in Mycobacterium smegmatis. McDermott, P.F., White, D.G., Podglajen, I., Alekshun, M.N., Levy, S.B. J. Bacteriol. (1998) [Pubmed]
  30. Leber's hereditary optic neuropathy mutations in ethambutol-induced optic neuropathy. Hwang, J.M., Kim, J., Park, S.S. J. Neurol. (2003) [Pubmed]
  31. Association of the Rv0679c protein with lipids and carbohydrates in Mycobacterium tuberculosis/Mycobacterium bovis BCG. Matsuba, T., Suzuki, Y., Tanaka, Y. Arch. Microbiol. (2007) [Pubmed]
  32. Caspase inhibitors block zinc-chelator induced death of retinal ganglion cells. Shindler, K.S., Zurakowski, D., Dreyer, E.B. Neuroreport (2000) [Pubmed]
  33. Tuberculoid tenosynovitis and carpal tunnel syndrome caused by Mycobacterium szulgai. Stratton, C.W., Phelps, D.B., Reller, L.B. Am. J. Med. (1978) [Pubmed]
  34. Effect of ethambutol on emergence of clarithromycin-resistant Mycobacterium avium complex in the beige mouse model. Bermudez, L.E., Nash, K.A., Petrofsky, M., Young, L.S., Inderlied, C.B. J. Infect. Dis. (1996) [Pubmed]
  35. Susceptibilities of nontuberculosis mycobacterial species to amoxicillin-clavulanic acid alone and in combination with antimycobacterial agents. Utrup, L.J., Moore, T.D., Actor, P., Poupard, J.A. Antimicrob. Agents Chemother. (1995) [Pubmed]
  36. Drug Therapy of Experimental Tuberculosis (TB): Improved Outcome by Combining SQ109, a New Diamine Antibiotic, with Existing TB Drugs. Nikonenko, B.V., Protopopova, M., Samala, R., Einck, L., Nacy, C.A. Antimicrob. Agents Chemother. (2007) [Pubmed]
  37. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Jia, L., Tomaszewski, J.E., Hanrahan, C., Coward, L., Noker, P., Gorman, G., Nikonenko, B., Protopopova, M. Br. J. Pharmacol. (2005) [Pubmed]
WikiGenes - Universities