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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/19 23:46:09」(JST)

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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[edit]

^ ^a ^b ^c "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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1. セカンドラインの抗結核療法 second line antituberculous therapy
2. 薬剤耐性結核の診断、治療、および予防 diagnosis treatment and prevention of drug resistant tuberculosis
3. 薬剤耐性結核の疫学および分子メカニズム epidemiology and molecular mechanisms of drug resistant tuberculosis
4. 甲状腺機能低下症の原因となる疾患 disorders that cause hypothyroidism
5. 広範囲薬剤耐性結核の臨床症状、診断、および治療 clinical manifestations diagnosis and treatment of extensively drug resistant tuberculosis

English Journal

Randomized Pilot Trial of Eight Weeks of Bedaquiline (TMC207) Treatment for Multidrug-Resistant Tuberculosis: Long-Term Outcome, Tolerability, and Effect on Emergence of Drug Resistance.

Diacon AH, Donald PR, Pym A, Grobusch M, Patientia RF, Mahanyele R, Bantubani N, Narasimooloo R, De Marez T, van Heeswijk R, Lounis N, Meyvisch P, Andries K, McNeeley DF.SourceFaculty of Health Sciences, Stellenbosch University, Tygerberg, South Africa.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2012 Jun;56(6):3271-6. Epub 2012 Mar 5.
The 2-year follow-up results for a randomized placebo-controlled study of 47 patients with multidrug-resistant pulmonary tuberculosis treated with either the new diarylquinoline TMC207, recently renamed bedaquiline, or placebo, added to the first 8 weeks of a background regimen, are presented. Bedaq
PMID 22391540

New times, new trends for ethionamide: In vitro evaluation of drug-loaded thermally carbonized porous silicon microparticles.

Vale N, Mäkilä E, Salonen J, Gomes P, Hirvonen J, Santos HA.SourceCentro de Investigação em Química da Universidade do Porto, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Porto, Portugal.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft für Pharmazeutische Verfahrenstechnik e.V.Eur J Pharm Biopharm.2012 Jun;81(2):314-23. Epub 2012 Mar 6.
Multidrug-resistant tuberculosis (MDR-TB) has become a worldwide problem and a major public health concern. The mechanisms of resistance are fairly well characterized for most agents, but MDR limits the therapeutic usefulness of both new and classical medicines against TB. Ethionamide (ETA) is a thi
PMID 22418076

Japanese Journal

サイクロセリンによる中枢神経障害を合併した多剤耐性結核の1例

藤田純一,砂田幸一,林宏紀 [他],林原賢治,斎藤武文
結核 83(1), 21-25, 2008-01-15
… We started chemotherapy with cycloserine (CS), ethionamide (TH), kanamycin (KM), pyrazinamide (PZA), para-aminosalicylic acid (PAS) and gatifloxacin (GFLX). …
NAID 10025688261

左荒蕪肺を呈した多剤耐性肺結核に左肺全摘術を施行した1例

小山和彦,川上健司,原田義高 [他],山領豪,木村由美子
結核 82(7), 577-581, 2007-07-15
… As the drug susceptibility test revealed that the isolated strain was multi-drug resistant, the regimen was changed to pyrazinamide, ethionamide, cycloserine, enviomycin, and levofloxacin. …
NAID 10019827586

抗結核薬による重症肝障害 : アンケート調査結果から

重藤えり子
結核 82(5), 467-473, 2007-05-15
… Twenty-three were treated by regimens with isoniazid (INH), rifampicin (RFP) and pyrazinamide (PZA), and 8 by regimens without PZA but with INH and RFP and one was a multidrug-resistant case and was treated by regimen with ethionamide and PZA. …
NAID 10019726986

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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	DB00609
ChemSpider	2041901
UNII	OAY8ORS3CQ
KEGG	D00591
ChEBI	CHEBI:4885
ChEMBL	CHEMBL1441
Chemical data
Formula	C8H10N2S
Mol. mass	166.244 g/mol
	SMILES S=C(c1ccnc(c1)CC)N;
	InChI InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11) ; Key:AEOCXXJPGCBFJA-UHFFFAOYSA-N ;
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　　[★]

英: ethionamide, ETH, ethioniamide
ラ: ethionamidum
商: ツベルミン
関: 抗結核薬

[GTCABoard-1] "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."

[pmid11823459-2] 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.

[pmid12878502-3] 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.

[pmid1416831-4] 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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ethionamide