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Chemical Compound Review

Ethinamat     (1-ethynylcyclohexyl) carbamate

Synonyms: Etinamate, Etinamato, Valamin, Valmidate, Volamin, ...
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Disease relevance of ethionamide


High impact information on ethionamide

  • A missense mutation within the mycobacterial inhA gene was shown to confer resistance to both INH and ethionamide (ETH) in M. smegmatis and in M. bovis [6].
  • The binding of hexadecyl octanoate to EthR induces a conformational state incompatible with repressor function, which should lead to ethA derepression and consequently to an increased sensitivity to ethionamide and other thioamides [1].
  • Thioamide drugs, ethionamide (ETH) and prothionamide (PTH), are clinically effective in the treatment of Mycobacterium tuberculosis, M. leprae, and M. avium complex infections [7].
  • Five weeks after discontinuation of ethionamide therapy, thyroid function had returned to normal [2].
  • The goitrogenic effect was studied in vitro by incubating ethionamide in various concentrations (10(-3) to 10(-7) mol/L) with ovine thyroid cells in tissue cultures [2].

Chemical compound and disease context of ethionamide


Biological context of ethionamide


Anatomical context of ethionamide


Associations of ethionamide with other chemical compounds


Gene context of ethionamide

  • ethA, inhA, and katG loci of ethionamide-resistant clinical Mycobacterium tuberculosis isolates [23].
  • Crystal structure of the TetR/CamR family repressor Mycobacterium tuberculosis EthR implicated in ethionamide resistance [14].
  • EthR has been shown to repress transcription of the activator gene ethA by binding to this intergenic region, thus contributing to ethionamide resistance [14].
  • Mutations that reduce NADH dehydrogenase activity (Ndh; type II) cause multiple phenotypes, including (i) coresistance to INH and a related drug, ethionamide; (ii) thermosensitive lethality; and (iii) auxotrophy [24].
  • For instance, the Affymetrix system revealed that Rv2524c (fas) was induced by both INH and ethionamide under the given levels of concentration, as suggested by most of the probe sets implementing this gene sequence [25].

Analytical, diagnostic and therapeutic context of ethionamide


  1. Structure of EthR in a ligand bound conformation reveals therapeutic perspectives against tuberculosis. Frénois, F., Engohang-Ndong, J., Locht, C., Baulard, A.R., Villeret, V. Mol. Cell (2004) [Pubmed]
  2. Ethionamide-induced goitrous hypothyroidism. Drucker, D., Eggo, M.C., Salit, I.E., Burrow, G.N. Ann. Intern. Med. (1984) [Pubmed]
  3. Ethionamide activation and sensitivity in multidrug-resistant Mycobacterium tuberculosis. DeBarber, A.E., Mdluli, K., Bosman, M., Bekker, L.G., Barry, C.E. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  4. Clinical pharmacokinetics of the antituberculosis drugs. Holdiness, M.R. Clinical pharmacokinetics. (1984) [Pubmed]
  5. Cerebrospinal fluid concentrations of ethionamide in children with tuberculous meningitis. Donald, P.R., Seifart, H.I. J. Pediatr. (1989) [Pubmed]
  6. inhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis. Banerjee, A., Dubnau, E., Quemard, A., Balasubramanian, V., Um, K.S., Wilson, T., Collins, D., de Lisle, G., Jacobs, W.R. Science (1994) [Pubmed]
  7. Mechanism of thioamide drug action against tuberculosis and leprosy. Wang, F., Langley, R., Gulten, G., Dover, L.G., Besra, G.S., Jacobs, W.R., Sacchettini, J.C. J. Exp. Med. (2007) [Pubmed]
  8. Enzymatic characterization of the target for isoniazid in Mycobacterium tuberculosis. Quémard, A., Sacchettini, J.C., Dessen, A., Vilcheze, C., Bittman, R., Jacobs, W.R., Blanchard, J.S. Biochemistry (1995) [Pubmed]
  9. Metabolism of Thioamides by Ralstonia pickettii TA. Dodge, A.G., Richman, J.E., Johnson, G., Wackett, L.P. Appl. Environ. Microbiol. (2006) [Pubmed]
  10. Oxidative activation of thiacetazone by the Mycobacterium tuberculosis flavin monooxygenase EtaA and human FMO1 and FMO3. Qian, L., Ortiz de Montellano, P.R. Chem. Res. Toxicol. (2006) [Pubmed]
  11. Resistance of multidrug-resistant strains of Mycobacterium tuberculosis from the Archangel oblast, Russia, to second-line anti-tuberculosis drugs. Toungoussova, O.S., Mariandyshev, A.O., Bjune, G., Caugant, D.A., Sandven, P. Eur. J. Clin. Microbiol. Infect. Dis. (2005) [Pubmed]
  12. Efficacy and safety of sparfloxacin in combination with kanamycin and ethionamide in multidrug-resistant pulmonary tuberculosis patients: preliminary results. Singla, R., Gupta, S., Gupta, R., Arora, V.K. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease. (2001) [Pubmed]
  13. The antituberculosis drug ethionamide is activated by a flavoprotein monooxygenase. Vannelli, T.A., Dykman, A., Ortiz de Montellano, P.R. J. Biol. Chem. (2002) [Pubmed]
  14. Crystal structure of the TetR/CamR family repressor Mycobacterium tuberculosis EthR implicated in ethionamide resistance. Dover, L.G., Corsino, P.E., Daniels, I.R., Cocklin, S.L., Tatituri, V., Besra, G.S., Fütterer, K. J. Mol. Biol. (2004) [Pubmed]
  15. Pharmacokinetics of ethionamide administered under fasting conditions or with orange juice, food, or antacids. Auclair, B., Nix, D.E., Adam, R.D., James, G.T., Peloquin, C.A. Antimicrob. Agents Chemother. (2001) [Pubmed]
  16. Effect of inhibitors of alpha-naphthylisothiocyanate-induced hepatotoxicity on the in vitro metabolism of alpha-naphthylisothiocyanate. Traiger, G.J., Vyas, K.P., Hanzlik, R.P. Chem. Biol. Interact. (1985) [Pubmed]
  17. Mutagenic activity of antileprosy drugs and their derivatives. Peters, J.H., Gordon, G.R., Murray, J.F., Simmon, V.F. Int. J. Lepr. Other Mycobact. Dis. (1983) [Pubmed]
  18. A comparison of the blood levels and urinary excretion of ethionamide and prothionamide in man. Jenner, P.J., Ellard, G.A., Gruer, P.J., Aber, V.R. J. Antimicrob. Chemother. (1984) [Pubmed]
  19. Cycloserine plus ethionamide plus pyrazinamide in the treatment of patients excreting isoniazid-resistant tubercle bacilli following previous chemotherapy. Ramakrishnan, C.V., Parthasarathy, R., Sambamoorthy, S., Somasundaram, P.R., Subbammal, S. Indian J. Med. Res. (1976) [Pubmed]
  20. Treatment of multibacillary leprosy with a regimen of 13 weeks duration. Pattyn, S.R., Groenen, G., Janssens, L., Kuykens, L., Mputu, L.B. Leprosy review. (1992) [Pubmed]
  21. Inhibitory effect of antituberculosis drugs on human cytochrome P450-mediated activities. Nishimura, Y., Kurata, N., Sakurai, E., Yasuhara, H. J. Pharmacol. Sci. (2004) [Pubmed]
  22. Neurological manifestations and toxicities of the antituberculosis drugs. A review. Holdiness, M.R. Medical toxicology. (1987) [Pubmed]
  23. ethA, inhA, and katG loci of ethionamide-resistant clinical Mycobacterium tuberculosis isolates. Morlock, G.P., Metchock, B., Sikes, D., Crawford, J.T., Cooksey, R.C. Antimicrob. Agents Chemother. (2003) [Pubmed]
  24. NADH dehydrogenase defects confer isoniazid resistance and conditional lethality in Mycobacterium smegmatis. Miesel, L., Weisbrod, T.R., Marcinkeviciene, J.A., Bittman, R., Jacobs, W.R. J. Bacteriol. (1998) [Pubmed]
  25. Exploring drug action on Mycobacterium tuberculosis using affymetrix oligonucleotide genechips. Fu, L.M. Tuberculosis (Edinburgh, Scotland) (2006) [Pubmed]
  26. Improved high-performance liquid chromatographic assay for the determination of ethionamide in serum. Peloquin, C.A., James, G.T., McCarthy, E. J. Chromatogr. (1991) [Pubmed]
  27. High-performance liquid chromatographic-tandem mass spectrometric method for the determination of ethionamide in human plasma, bronchoalveolar lavage fluid and alveolar cells. Conte, J.E., Wang, G., Lin, E.T., Zurlinden, E. J. Chromatogr. B Biomed. Sci. Appl. (2001) [Pubmed]
  28. Polymeric colloidal systems containing ethionamide: preparation and physico-chemical characterization. Lopes, E., Pohlmann, A.R., Bassani, V., Guterres, S.S. Die Pharmazie. (2000) [Pubmed]
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