Ethionamide

Catalog No.S1777 Synonyms: Bayer 5312

For research use only.

Ethionamide (Bayer 5312) is an antibiotic used in the treatment of tuberculosis.

Ethionamide Chemical Structure

CAS No. 536-33-4

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Biological Activity

Description Ethionamide (Bayer 5312) is an antibiotic used in the treatment of tuberculosis.
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. [1] 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. [2] 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. [3] 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. [4]

Protocol (from reference)

Solubility (25°C)

In vitro

Chemical Information

Molecular Weight 166.24
Formula

C8H10N2S

CAS No. 536-33-4
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CCC1=NC=CC(=C1)C(=S)N

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Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05258877 Not yet recruiting Other: Plasma samples Tuberculosis Pulmonary BioVersys AG|TASK Applied Science March 30 2022 --

(data from https://clinicaltrials.gov, updated on 2022-08-01)

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