Ethionamide

Ethionamide
Clinical data
Trade names	Trecator, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682402
Routes of; administration	by mouth
ATC code	J04AD03 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	~30%
Elimination half-life	2 to 3 hours
Identifiers
	IUPAC name 2-ethylpyridine-4-carbothioamide;
CAS Number	536-33-4 ;
PubChem CID	2761171;
DrugBank	DB00609 ;
ChemSpider	2041901 ;
UNII	OAY8ORS3CQ;
KEGG	D00591 ;
ChEBI	CHEBI:4885 ;
ChEMBL	ChEMBL1441 ;
CompTox Dashboard (EPA)	DTXSID0020577 ;
ECHA InfoCard	100.007.846
Chemical and physical data
Formula	C8H10N2S
Molar mass	166.24 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	164 to 166 °C (327 to 331 °F) (dec.)
	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 ;
	(verify)

Ethionamide is an antibiotic used to treat tuberculosis.^[2] Specifically it is used, along with other antituberculosis medications, to treat active multidrug-resistant tuberculosis.^[2] It is no longer recommended for leprosy.^[3]^[2] It is taken by mouth.^[2]

Ethionamide has a high rate of side effects.^[4] Common side effects include nausea, diarrhea, abdominal pain, and loss of appetite. Serious side effects may include liver inflammation and depression. It should not be used in people with significant liver problems. Use in pregnancy is not recommended as safety is unclear.^[2] Ethionamide is in the thioamides family of medications. It is believed to work by interfering with the use of mycolic acid.^[5]

Ethionamide was discovered in 1956 and approved for medical use in the United States in 1965.^[5]^[2] It is on the World Health Organization's List of Essential Medicines.^[6]

^ "Trecator- ethionamide tablet, film coated". DailyMed. 20 May 2020. Retrieved 28 July 2020.
^ ^a ^b ^c ^d ^e ^f "Ethionamide". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ "Standard Chemotherapy". www.hrsa.gov. Archived from the original on 2016-12-20. Retrieved 2016-12-15.
^ Wolff KA, Nguyen L (September 2012). "Strategies for potentiation of ethionamide and folate antagonists against Mycobacterium tuberculosis". Expert Review of Anti-Infective Therapy. 10 (9): 971–981. doi:10.1586/eri.12.87. PMC 3971469. PMID 23106273.
^ ^a ^b "Ethionamide". TB Online. Global Tuberculosis Community Advisory Board. Archived from the original on 2013-09-14. Retrieved 2012-08-18.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Trecator_FDA_label-1] "Trecator- ethionamide tablet, film coated". DailyMed. 20 May 2020. Retrieved 28 July 2020.

[AHFS2016-2] ^ ^a ^b ^c ^d ^e ^f "Ethionamide". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.

[3] "Standard Chemotherapy". www.hrsa.gov. Archived from the original on 2016-12-20. Retrieved 2016-12-15.

[Wol2012-4] Wolff KA, Nguyen L (September 2012). "Strategies for potentiation of ethionamide and folate antagonists against Mycobacterium tuberculosis". Expert Review of Anti-Infective Therapy. 10 (9): 971–981. doi:10.1586/eri.12.87. PMC 3971469. PMID 23106273.

[GTC2012-5] "Ethionamide". TB Online. Global Tuberculosis Community Advisory Board. Archived from the original on 2013-09-14. Retrieved 2012-08-18.

[WHO21st-6] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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