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E6005

Sigma-Aldrich

Ethionamide

≥98.0%, suitable for ligand binding assays

Synonym(s):

2-Ethyl-4-pyridinecarbothioamide

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About This Item

Empirical Formula (Hill Notation):
C8H10N2S
CAS Number:
536-33-4
Molecular Weight:
166.24
EC Number:
208-628-9
MDL number:
MFCD00057361
UNSPSC Code:
12352111
PubChem Substance ID:
24894350
NACRES:
NA.26

product name

Ethionamide,

Assay

≥98.0%

form

powder

technique(s)

ligand binding assay: suitable

color

yellow

storage temp.

2-8°C

SMILES string

CCc1cc(ccn1)C(N)=S

InChI

1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)

InChI key

AEOCXXJPGCBFJA-UHFFFAOYSA-N

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General description

Ethionamide (ETA, ETH), a thioamide, is an anti-tuberculosis agent used as a second-line therapy in treating tuberculosis when other agents are not effective. The structure of ETA is similar to isoniazid.

Application

Ethionamide is used in antimicrobials and in potency assay of test compounds on M. tuberculosis.

Biochem/physiol Actions

Ethionamide is used as an anti-tuberculosis antibiotic and an inducer of hypothyroidism.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H361

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S Thee et al.
Tuberculosis (Edinburgh, Scotland), 97, 126-136 (2015-11-21)
Ethionamide (ETH) and prothionamide (PTH), both thioamides, have proven efficacy in clinical studies and form important components for multidrug-resistant tuberculosis treatment regimens and for treatment of tuberculous meningitis in adults and children. ETH and PTH are pro-drugs that, following enzymatic
Marion Flipo et al.
Journal of medicinal chemistry, 54(8), 2994-3010 (2011-03-23)
We report in this article an extensive structure-activity relationships (SAR) study with 58 thiophen-2-yl-1,2,4-oxadiazoles as inhibitors of EthR, a transcriptional regulator controling ethionamide bioactivation in Mycobacterium tuberculosis. We explored the replacement of two key fragments of the starting lead BDM31343.
Lack of cross-toxicity between isoniazid and ethionamide in severe cutaneous adverse drug reactions: a series of 25 consecutive confirmed cases.
Lehloenya RJ, et al.
The Journal of Antimicrobial Chemotherapy, 70(9), 2648-2651 (2015)
Abhijeet Y Deshpande et al.
Biomedical chromatography : BMC, 25(9), 985-994 (2011-01-27)
A highly sensitive and specific LC-MS/MS method has been developed for simultaneous quantification of ethionamide and ethionamide sulfoxide in human plasma (300 µL) using prothionamide as an internal standard (IS). Solid-phase extraction was used to extract ethionamide, ethionamide sulfoxide and IS
Catherine Vilchèze et al.
Antimicrobial agents and chemotherapy, 55(9), 4422-4423 (2011-06-29)
A search to identify new mechanisms of isoniazid resistance in Mycobacterium bovis led to the isolation of mutants defective in mycothiol biosynthesis due to mutations in genes coding for the glycosyltransferase (mshA) or the cysteine ligase (mshC). These mutants showed
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