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{{drugbox | IUPAC_name = 2-ethylpyridine-4-carbothioamide | image = Ethionamide.png | CAS_number = 536-33-4 | ATC_prefix = J04 | ATC_suffix = AD03 | ATC_supplemental = | PubChem = 2761171 | DrugBank = APRD00961 | C=8 | H=10 | N=2 | S=1 | molecular_weight = 166.244 g/mol | bioavailability = | protein_bound = Approximately 30% bound to proteins. | metabolism = | elimination_half-life = 2 to 3 hours | pregnancy_category = | legal_status = | routes_of_administration = }}
{{SI}}


__NOTOC__
{{Ethionamide}}
{{CMG}} ;  {{AE}}  {{chetan}}


'''Ethionamide''' (2-ethylthioisonicotinamide, Trecator SC®) is an [[antibiotic]] used in the treatment of [[tuberculosis]].
==Overview==
'''Ethionamide''' (2-ethylthioisonicotinamide, Trecator SC) is an [[antibiotic]] used in the treatment of [[tuberculosis]]. It was [[1956 in science#Medicine|discovered in 1956]].<ref name="GTCABoard">{{cite web| publisher= Global Tuberculosis Community Advisory Board | url= http://www.tbonline.info/posts/2011/8/24/ethionamide/ | title= Ethionamide | work= TB Online | quote= 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 [[Multi-drug-resistant tuberculosis|MDR]] and [[Extensively drug-resistant tuberculosis|XDR TB]]. It was discovered in 1956.  Ethionamide is used as part of a South Africa’s standard regimen to treat MDR TB.| accessdate}}</ref>


{{Antimycobacterials}}
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]]<ref name="pmid11823459">{{cite journal |author=Vannelli TA, Dykman A, Ortiz de Montellano PR |title=The anti-tuberculosis drug ethionamide is activated by a flavoprotein monooxygenase |journal=J. Biol. Chem. |volume=277 |issue=15 |pages=12824–9 |year=2002 |month=April |pmid=11823459 |doi=10.1074/jbc.M110751200 |url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=11823459}}</ref> and as a [[thioamide]], it is used in [[regimen]]s to treat [[multi-drug-resistant tuberculosis|multi-drug-resistant]] and [[extensively drug-resistant tuberculosis|extensively drug-resistant]] tuberculosis.<ref name="GTCABoard"/>
It has been proposed for use in combination with [[gatifloxacin]].<ref name="pmid12878502">{{cite journal |author=Cynamon MH, Sklaney M |title=Gatifloxacin and ethionamide as the foundation for therapy of tuberculosis |journal=Antimicrob. Agents Chemother. |volume=47 |issue=8 |pages=2442–4 |year=2003 |month=August |pmid=12878502 |pmc=166105 |doi= 10.1128/AAC.47.8.2442-2444.2003|url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=12878502}}</ref>
==Category==
Antimycobacterial
==US Brand Names==


[[Category:Antibiotics]]
<sup>TRECATOR''''''</sup>
[[Category:Pyridines]]
==FDA Package Insert==
'''[[Ethionamide description|Description]]'''
'''| [[Ethionamide clinical pharmacology|Clinical Pharmacology]]'''
'''| [[Ethionamide microbiology|Microbiology]]'''
'''| [[Ethionamide indications and usage|Indications and Usage]]'''
'''| [[Ethionamide contraindications|Contraindications]]'''
'''| [[Ethionamide warnings and precautions|Warnings and Precautions]]'''
'''| [[Ethionamide adverse reactions|Adverse Reactions]]'''
'''| [[Ethionamide overdosage|Overdosage]]'''
'''| [[Ethionamide clinical studies|Clinical Studies]]'''
'''| [[Ethionamide dosage and administration|Dosage and Administration]]'''
'''| [[Ethionamide compatibility reconstitution and stability|Compatibility, Reconstitution, and Stability]]'''
'''| [[Ethionamide directions for use|Directions For Use]]'''
'''| [[Ethionamide how supplied|How Supplied]]'''
'''| [[Ethionamide labels and packages|Labels and Packages]]'''


==Mechanisms of Action==
The action may be through disruption of [[mycolic acid]].<ref name="GTCABoard"/><ref name="pmid1416831">{{cite journal |author=Quémard A, Lanéelle G, Lacave C |title=Mycolic acid synthesis: a target for ethionamide in mycobacteria? |journal=Antimicrob. Agents Chemother. |volume=36 |issue=6 |pages=1316–21 |year=1992 |month=June |pmid=1416831 |pmc=190338 |doi= |url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=1416831}}</ref>


==References==
{{Reflist|2}}


{{WH}}
[[Category:Antibiotics]]
{{WS}}
[[Category:Wikinfect]]

Revision as of 13:23, 27 December 2013


Ethionamide
TRECATOR® FDA Package Insert
Description
Clinical Pharmacology
Microbiology
Indications and Usage
Contraindications
Warnings and Precautions
Adverse Reactions
Overdosage
Dosage and Administration
How Supplied
Labels and Packages

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1] ; Associate Editor(s)-in-Chief: Chetan Lokhande, M.B.B.S [2]

Overview

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]

Category

Antimycobacterial

US Brand Names

TRECATOR'

FDA Package Insert

Description | Clinical Pharmacology | Microbiology | Indications and Usage | Contraindications | Warnings and Precautions | Adverse Reactions | Overdosage | Clinical Studies | Dosage and Administration | Compatibility, Reconstitution, and Stability | Directions For Use | How Supplied | Labels and Packages

Mechanisms of Action

The action may be through disruption of mycolic acid.[1][4]

References

  1. ↑ 1.0 1.1 1.2 "Ethionamide". TB Online. Global Tuberculosis Community Advisory Board. 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. Text " accessdate" ignored (help)
  2. ↑ Vannelli TA, Dykman A, Ortiz de Montellano PR (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. Unknown parameter |month= ignored (help)
  3. ↑ Cynamon MH, Sklaney M (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. Unknown parameter |month= ignored (help)
  4. ↑ Quémard A, Lanéelle G, Lacave C (1992). "Mycolic acid synthesis: a target for ethionamide in mycobacteria?". Antimicrob. Agents Chemother. 36 (6): 1316–21. PMC 190338. PMID 1416831. Unknown parameter |month= ignored (help)
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