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Chemical Compound Review

Trecator     2-ethylpyridine-4- carbothioamide

Synonyms: Amidazin, Ethimide, Iridocin, Amidazine, ethionamide, ...
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Disease relevance of ethionamide


High impact information on ethionamide

  • EtaA is a newly identified FAD-containing monooxygenase that is responsible for activation of several thioamide prodrugs in Mycobacterium tuberculosis [6].
  • A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC [7].
  • Comparisons show that, while NADP+ and NADPH bind to DHFR with the pyridine ring and 3'-carboxamide coplanar, the thioamide group is twisted by 23 degrees from the pyridine plane in both the binary and ternary complexes [8].
  • The effects of changes in pyridyl group, thioamide, and thiane ring on in vitro K(+)-channel opening reactivity are discussed [9].
  • A series of aldose reductase inhibitors was prepared in which structural modifications were made to three positions of the potent, orally active inhibitor tolrestat (1), namely, the 6-methoxy substituent, thioamide sulfur, and the N-methyl moiety [10].

Chemical compound and disease context of ethionamide

  • The effect of methimazole on thioamide bioactivation and toxicity [11].
  • During amiodarone therapy, the clinical features of thyrotoxicosis may be masked or atypical, and the choice of therapy is complicated by a delayed response to thioamide drugs and possible contraindication for beta-blocking agents which necessitates the use of glucocorticoid drugs in some patients [12].

Biological context of ethionamide

  • Alkylation, allylation, and silylation took place selectively at the carbon atom adjacent to the nitrogen atom of the thioamide dianions [13].
  • Thioamide therapy has improved the outcome of pregnancies complicated by maternal hyperthyroidism, without long-term effects on cognitive and somatic development [14].
  • Synthesis and QSAR studies of novel triazole compounds containing thioamide as potential antifungal agents [15].
  • From molecular free energy calculations, it is shown that the main influence of the introduction of a thioamide bond on the molecular structure is to prevent the existence of C7(eq) conformations involving the thiomethionine residue [16].
  • Although single amino acid substitutions (e.g. Aib) can restrict the available conformations, they do not necessarily lead to unique conformers, however, we predict that some of the amino acids described in this report will fold to a single phi, psi conformation (e.g. N-methylated and thioamide penicillamine) [17].

Anatomical context of ethionamide

  • Our review also indicates that impairment of neonatal thyroid function may be minimized by using a thioamide dose that is just sufficient to maintain the maternal serum free thyroxine concentration in the high normal or slightly thyrotoxic range [14].

Associations of ethionamide with other chemical compounds


Gene context of ethionamide

  • Carbobenzoxythioglycyl-L-phenylalanine [CbzNHCH2C(==S)Phe, Z-Glys-Phe] was synthesized as thioamide analogue of Z-Gly-Phe, a known substrate of carboxypeptidase A (CPA) [23].
  • Solid phase synthesis of a GHRP analog containing C-terminal thioamide group [24].
  • Axially chiral thioamide ligands L5, L6, L8, L11, and bis(thioamide) ligand L13 were prepared from the reaction of (S)-(-)-1,1'-binaphthyl-2,2'-diamine with acyl chlorides and phosphorus pentasulfide (P2S5) [25].
  • Thioamide substrate probes of metal-substrate interactions in carboxypeptidase A catalysis [26].
  • TRH analogue with C-terminal thioamide group: rapid degradation by plasma and its biological effects [27].

Analytical, diagnostic and therapeutic context of ethionamide


  1. 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]
  2. 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]
  3. Synthesis, cytotoxicity, and antiviral activity of some acyclic analogues of the pyrrolo[2,3-d]pyrimidine nucleoside antibiotics tubercidin, toyocamycin, and sangivamycin. Gupta, P.K., Daunert, S., Nassiri, M.R., Wotring, L.L., Drach, J.C., Townsend, L.B. J. Med. Chem. (1989) [Pubmed]
  4. Synthesis, cytotoxicity, and antiviral activity of certain 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine nucleosides related to toyocamycin and sangivamycin. Gupta, P.K., Nassiri, M.R., Coleman, L.A., Wotring, L.L., Drach, J.C., Townsend, L.B. J. Med. Chem. (1989) [Pubmed]
  5. Synthesis of thioamide bond catalyzed by E. coli ribosomes. Victorova, L.S., Kotusov, V.V., Azhaev, A.V., Krayevsky, A.A., Kukhanova, M.K., Gottikh, B.P. FEBS Lett. (1976) [Pubmed]
  6. The prodrug activator EtaA from Mycobacterium tuberculosis is a Baeyer-Villiger monooxygenase. Fraaije, M.W., Kamerbeek, N.M., Heidekamp, A.J., Fortin, R., Janssen, D.B. J. Biol. Chem. (2004) [Pubmed]
  7. The first potent inhibitors for human glutaminyl cyclase: synthesis and structure-activity relationship. Buchholz, M., Heiser, U., Schilling, S., Niestroj, A.J., Zunkel, K., Demuth, H.U. J. Med. Chem. (2006) [Pubmed]
  8. Crystal structures of chicken liver dihydrofolate reductase: binary thioNADP+ and ternary thioNADP+.biopterin complexes. McTigue, M.A., Davies, J.F., Kaufman, B.T., Kraut, J. Biochemistry (1993) [Pubmed]
  9. Synthesis and biological activity of trans(+-)-N-methyl-2-(3-pyridyl)-2-tetrahydrothiopyrancarbothioamide 1-oxide (RP 49356) and analogues: a new class of potassium channel opener. Brown, T.J., Chapman, R.F., Cook, D.C., Hart, T.W., McLay, I.M., Jordan, R., Mason, J.S., Palfreyman, M.N., Walsh, R.J., Withnall, M.T. J. Med. Chem. (1992) [Pubmed]
  10. Orally active aldose reductase inhibitors derived from bioisosteric substitutions on tolrestat. Wrobel, J., Millen, J., Sredy, J., Dietrich, A., Kelly, J.M., Gorham, B.J., Sestanj, K. J. Med. Chem. (1989) [Pubmed]
  11. The effect of methimazole on thioamide bioactivation and toxicity. Ruse, M.J., Waring, R.H. Toxicol. Lett. (1991) [Pubmed]
  12. Amiodarone. The dilemma of hyperthyroxinaemia and the treatment of thyrotoxicosis. Donaghue, K.C., Clarke, P., Hooper, M.J. Med. J. Aust. (1985) [Pubmed]
  13. Reaction and characterization of thioamide dianions derived from N-benzyl thioamides. Murai, T., Aso, H., Tatematsu, Y., Itoh, Y., Niwa, H., Kato, S. J. Org. Chem. (2003) [Pubmed]
  14. Review of antithyroid drug use during pregnancy and report of a case of aplasia cutis. Mandel, S.J., Brent, G.A., Larsen, P.R. Thyroid (1994) [Pubmed]
  15. Synthesis and QSAR studies of novel triazole compounds containing thioamide as potential antifungal agents. Wei, Q.L., Zhang, S.S., Gao, J., Li, W.H., Xu, L.Z., Yu, Z.G. Bioorg. Med. Chem. (2006) [Pubmed]
  16. Crystal and molecular structure of two geometrically restricted chemotactic tripeptides, analogues of formyl-methionine-leucine-phenylalanine. Michel, A.G., Lajoie, G., Hassani, C.A. Int. J. Pept. Protein Res. (1990) [Pubmed]
  17. Designing amino acid residues with single-conformations. Tran, T.T., Treutlein, H., Burgess, A.W. Protein Eng. Des. Sel. (2006) [Pubmed]
  18. Synthesis of sulfur-containing analogues of bestatin. Inhibition of aminopeptidases by alpha-thiolbestatin analogues. Ocain, T.D., Rich, D.H. J. Med. Chem. (1988) [Pubmed]
  19. Fluorogenic Hg2+-selective chemodosimeter derived from 8-hydroxyquinoline. Song, K.C., Kim, J.S., Park, S.M., Chung, K.C., Ahn, S., Chang, S.K. Org. Lett. (2006) [Pubmed]
  20. The mabA gene from the inhA operon of Mycobacterium tuberculosis encodes a 3-ketoacyl reductase that fails to confer isoniazid resistance. Banerjee, A., Sugantino, M., Sacchettini, J.C., Jacobs, W.R. Microbiology (Reading, Engl.) (1998) [Pubmed]
  21. Catalytic activity and substrate specificity of the flavin-containing monooxygenase in microsomal systems: characterization of the hepatic, pulmonary and renal enzymes of the mouse, rabbit, and rat. Tynes, R.E., Hodgson, E. Arch. Biochem. Biophys. (1985) [Pubmed]
  22. Synthesis and biological evaluation of a series of hydroxybenzylphenylamine derivatives as inhibitors of EGF receptor-associated tyrosine kinase activity. Chen, H., Bashiardes, G., Mailliet, P., Commercon, A., Sounigo, F., Boiziau, J., Parker, F., Tocque, B., Roques, B.P., Garbay, C. Anticancer Drug Des. (1996) [Pubmed]
  23. A thioamide substrate of carboxypeptidase A. Bartlett, P.A., Spear, K.L., Jacobsen, N.E. Biochemistry (1982) [Pubmed]
  24. Solid phase synthesis of a GHRP analog containing C-terminal thioamide group. Majer, Z., Zewdu, M., Hollósi, M., Sepródi, J., Vadász, Z., Teplán, I. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  25. Axially dissymmetric N-thioacylated (S)-(-)-1,1'-binaphthyl-2,2'-diamine ligands for copper-catalyzed asymmetric Michael addition of diethylzinc to alpha,beta-unsaturated ketone. Shi, M., Duan, W.L., Rong, G.B. Chirality. (2004) [Pubmed]
  26. Thioamide substrate probes of metal-substrate interactions in carboxypeptidase A catalysis. Bond, M.D., Holmquist, B., Vallee, B.L. J. Inorg. Biochem. (1986) [Pubmed]
  27. TRH analogue with C-terminal thioamide group: rapid degradation by plasma and its biological effects. Angyal, R., Strbák, V., Alexandrová, M., Kruszyński, M. Endocrinol. Exp. (1985) [Pubmed]
  28. Relationship between cytotoxicity and conversion of thiosangivamycin analogs to toyocamycin analogs in cell culture medium. Renau, T.E., Lee, J.S., Kim, H., Young, C.G., Wotring, L.L., Townsend, L.B., Drach, J.C. Biochem. Pharmacol. (1994) [Pubmed]
  29. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Klimesová, V., Zahajská, L., Waisser, K., Kaustová, J., Möllmann, U. Farmaco (2004) [Pubmed]
  30. Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin. Moody, C.J., Slawin, A.M., Willows, D. Org. Biomol. Chem. (2003) [Pubmed]
  31. Toxicity assessment of 255 chemicals to pure cultured nitrifying bacteria using biosensor. Tanaka, Y., Taguchi, K., Utsumi, H. Water Sci. Technol. (2002) [Pubmed]
  32. Simple, rapid and sensitive determination of protionamide in human serum by high-performance liquid chromatography. Bartels, H., Bartels, R. J. Chromatogr. B Biomed. Sci. Appl. (1998) [Pubmed]
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