Ethionamide

SKU: orb1309547

Description

Ethionamide is a second-line antitubercular agent that inhibits mycolic acid synthesis, disrupting the bacterial cell wall. It is used in research involving drug-resistant Mycobacterium tuberculosis, with applications in both in vitro susceptibility testing and in vivo animal models of tuberculosis infection.

Research Area

Pharmacology & Drug Discovery

Key Properties

• CAS Number: 536-33-4
• MW: 166.24
• Purity: 99.92% (May vary between batches)
• Formula: C₈H₁₀N₂S
• SMILES: C(N)(=S)C=1C=C(CC)N=CC1
• Target: Dehydrogenase,Antibiotic,Antibacterial
• Solubility: H2O:< 1 mg/mL (insoluble or slightly soluble);Ethanol:14 mg/mL (84.22 mM);DMSO:75 mg/mL (451.15 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:5 mg/mL (30.08 mM)

Bioactivity

• In Vitro:
  Ethionamide is a structural analogue of isoniazid (INH), both are pro-drugs that need to be activated by mycobacterial enzymes to exert their antimicrobial activity. Ethionamide mechanism of action is thought to be identical to INH although the pathway of activation is distinct from that of INH. Ethionamide is activated by an EthA enzyme, leading to the formation of a Soxide metabolite that has considerably better activity than the parent drug. Ethionamide inhibits both biofilm formation and viability of mature biofilms. Ethionamide reduces the content of ergosterol in Cryptococcus spp. planktonic cells and destabilized or permeabilized the fungal cell membrane, leading to leakage of macromolecules. Ethionamide is in general toxic at concentrations above 0.50 mM to HepG2, Caco-2, and RAW macrophage cells, but the toxicity is drastically reduced when Ethionamide is loaded into the microparticles. Ethionamide shows a fast metabolization process in the presence of the thermally carbonized- Porous silicon (TCPSi) particles. Ethionamide is activated in Mycobacterium tuberculosis by the protein encoded by the gene Rv3854c. Ethionamide appear to disrupt cell wall biosynthesis and have at least one common cellular target, the enoyl-acyl carrier protein reductase InhA.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Bacterial, Antibiotic, Bayer 5312, CAT, 2-ethylthioisonicotinamide, Ethionamide, Ethinamide, Inhibitor, inhibit, NAPDH

Compound Identifiers

PubChem CID

2761171