Ethionamide
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|---|---|
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| Systematic (IUPAC) name | |
| 2-ethylpyridine-4-carbothioamide | |
| Clinical data | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682402 |
| 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 | DB00609 |
| ChemSpider | 2041901 |
| UNII | OAY8ORS3CQ |
| KEGG | D00591 |
| ChEBI | CHEBI:4885 |
| ChEMBL | CHEMBL1441 |
| Chemical data | |
| Formula | C8H10N2S |
| Mol. mass | 166.244 g/mol |
| SMILES
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| (what is this?) (verify) | |
Ethionamide (2-ethylthioisonicotinamide, Trecator SC) is an antibiotic used in the treatment of tuberculosis. It was discovered in 1956.[1]
Ethionamide is activated by EthA, a mono-oxygenase in Mycobacterium tuberculosis, and binds NAD to form an adduct which inhibits InhA in the same way as isoniazid. Expression of the ethA gene is controlled by EthR, a transcriptional repressor. It is understood that improving ethA expression will increase the efficacy of ethionamide and so EthR inhibitors are of great interest to co-drug developers.
It is a prodrug[2] and as a thioamide, it is used in regimens to treat multi-drug-resistant and extensively drug-resistant tuberculosis.[1]
It has been proposed for use in combination with gatifloxacin.[3]
The action may be through disruption of mycolic acid.[1][4]
References
- ↑ 1.0 1.1 1.2 "Ethionamide". TB Online. Global Tuberculosis Community Advisory Board. Retrieved 2012-08-18. "Ethionamide is part of a group of drugs used in the treatment of drug resistant TB called thioamides. It is used as part of treatment regimens, generally involving 5 medicines, to treat MDR and XDR TB. It was discovered in 1956. Ethionamide is used as part of a South Africa’s standard regimen to treat MDR TB."
- ↑ Vannelli TA, Dykman A, Ortiz de Montellano PR (April 2002). "The anti-tuberculosis drug ethionamide is activated by a flavoprotein monooxygenase". J. Biol. Chem. 277 (15): 12824–9. doi:10.1074/jbc.M110751200. PMID 11823459.
- ↑ 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.
- ↑ 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.
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