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
EC Number:
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.26
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Product Name
Ethionamide,
Assay
≥98.0%
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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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
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
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
Fluorimetric determination of ethionamide in pharmaceutical preparations and biological fluids.
Walash MI, et al.
J. Chin. Chem. Soc., 51(5A), 1059-1064 (2004)
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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