An antimycobacterial compound
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Labeled Version(s)
33636Ethionamide-d3
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Ethionamide

Item No. 23714

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-ethyl-4-pyridinecarbothioamide
CAS Number
536-33-4
Synonyms
  • NSC 255115
Molecular Formula
C8H10N2S
Formula Weight
166.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Slightly Soluble
λmax
290 nm
SMILES
CCC1=CC(C(N)=S)=CC=N1
InChi Code
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
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Ethionamide is an antimycobacterial compound that is active against M. tuberculosis (MICs = 0.3-1.25 µg/ml).1,2 It is activated via oxidation by flavin monooxygenase and inhibits the InhA enzyme involved in mycolic acid biosynthesis.1 Formulations containing ethionamide have been used in the second-line treatment of multi-drug resistant tuberculosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Laborde, J., Deraeve, C., and Bernardes-Génisson, V. Update of antitubercular prodrugs from a molecular perspective: Mechanisms of action, bioactivation pathways, and associated resistance. ChemMedChem 12(20), 1657-1676 (2017).

    2. Heifets, L.B., Lindholm-Levy, P.J., and Flory, M. Comparison of bacteriostatic and bactericidal activity of isoniazid and ethionamide against Mycobacterium avium and Mycobacterium tuberculosis. Am. Rev. Respir. Dis. 143(2), 268-270 (1991).