E6005
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:
Molecular Weight:
166.24
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352111
EC Number:
208-628-9
MDL number:
Product Name
Ethionamide,
InChI key
AEOCXXJPGCBFJA-UHFFFAOYSA-N
InChI
1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
SMILES string
CCc1cc(ccn1)C(N)=S
assay
≥98.0%
form
powder
technique(s)
ligand binding assay: suitable
color
yellow
storage temp.
2-8°C
Quality Level
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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.
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Repr. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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Marion Flipo et al.
Journal of medicinal chemistry, 55(1), 68-83 (2011-11-22)
Mycobacterial transcriptional repressor EthR controls the expression of EthA, the bacterial monooxygenase activating ethionamide, and is thus largely responsible for the low sensitivity of the human pathogen Mycobacterium tuberculosis to this antibiotic. We recently reported structure-activity relationships of a series
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
Fluorimetric determination of ethionamide in pharmaceutical preparations and biological fluids.
Walash MI, et al.
J. Chin. Chem. Soc., 51(5A), 1059-1064 (2004)
Liang-Chun Chen et al.
BMC systems biology, 6, 5-5 (2012-01-20)
Drug resistance has now posed more severe and emergent threats to human health and infectious disease treatment. However, wet-lab approaches alone to counter drug resistance have so far still achieved limited success due to less knowledge about the underlying mechanisms
A E DeBarber et al.
Proceedings of the National Academy of Sciences of the United States of America, 97(17), 9677-9682 (2000-08-16)
Ethionamide (ETA) is an important component of second-line therapy for the treatment of multidrug-resistant tuberculosis. Synthesis of radiolabeled ETA and an examination of drug metabolites formed by whole cells of Mycobacterium tuberculosis (MTb) have allowed us to demonstrate that ETA
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