Ethionamide

Ethionamide
Systematic (IUPAC) name
2-ethylpyridine-4-carbothioamide
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682402
Pregnancy cat.  ?
Legal status  ?
Pharmacokinetic data
Protein binding Approximately 30% bound to proteins.
Half-life 2 to 3 hours
Identifiers
CAS number 536-33-4
ATC code J04AD03
PubChem CID 2761171
DrugBank APRD00961
ChemSpider 2041901 YesY
UNII OAY8ORS3CQ YesY
KEGG D00591 YesY
ChEBI CHEBI:4885 YesY
ChEMBL CHEMBL1441 YesY
Chemical data
Formula C8H10N2S 
Mol. mass 166.244 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Ethionamide (2-ethylthioisonicotinamide, Trecator SC) is an antibiotic used in the treatment of tuberculosis.

It is a prodrug.[1]

It has been proposed for use in combination with gatifloxacin.[2]

The action may be through disruption of mycolic acid.[3]

Synthesis

Ethionamide synth.png

Liberman, D.; Rist, N.; Grumbach, F.; Cals, S.; Moyeux, M.; Rouaix, A.; Bull. Soc. Chim. Fr. 1958, 687.

References

  1. ^ Vannelli TA, Dykman A, Ortiz de Montellano PR (April 2002). "The antituberculosis drug ethionamide is activated by a flavoprotein monooxygenase". J. Biol. Chem. 277 (15): 12824–9. doi:10.1074/jbc.M110751200. PMID 11823459. http://www.jbc.org/cgi/pmidlookup?view=long&pmid=11823459. 
  2. ^ Cynamon MH, Sklaney M (August 2003). "Gatifloxacin and ethionamide as the foundation for therapy of tuberculosis". Antimicrob. Agents Chemother. 47 (8): 2442–4. doi:10.1128/AAC.47.8.2442-2444.2003. PMC 166105. PMID 12878502. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=12878502. 
  3. ^ Quémard A, Lanéelle G, Lacave C (June 1992). "Mycolic acid synthesis: a target for ethionamide in mycobacteria?". Antimicrob. Agents Chemother. 36 (6): 1316–21. PMC 190338. PMID 1416831. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=1416831.