Ethionamide

• CAT Number: A000497
• CAS Number: 536-33-4
• Molecular Formula: C8H10N2S
• Molecular Weight: 166.24
• Purity: ≥95%
• Synonyms: 536-33-4; Ethinamide; Ethioniamide; 2-ethylpyridine-4-carbothioamide; Amidazine
• Target: Bacterial
• Solubility: >7.7mg/mL in DMSO
• Storage: -20°C
• IUPAC Name: 2-ethylpyridine-4-carbothioamide
• InChI: InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
• InChIKey: AEOCXXJPGCBFJA-UHFFFAOYSA-N
• SMILES: CCC1=NC=CC(=C1)C(=S)N

Ethionamide（Cat No.:A000497）is a prodrug and second-line antibiotic primarily used to treat tuberculosis (TB), particularly in multi-drug resistant cases. It targets Mycobacterium tuberculosis by inhibiting the synthesis of mycolic acids, essential components of the bacterial cell wall, leading to cell death. Activated within the bacterial cell, Ethionamide is often studied for its role in TB resistance mechanisms and its interactions in combination therapies. Its unique action against resistant TB strains makes it valuable in research focused on enhancing TB treatment efficacy and developing new strategies to combat persistent infections.

 

Reference

1: de Welzen L, Eldholm V, Maharaj K, Manson AL, Earl AM, Pym AS. Whole
transcriptome and genomic analysis of extensively drug-resistant Mycobacterium
tuberculosis clinical isolates identifies downregulation of ethA as a mechanism
of ethionamide resistance. Antimicrob Agents Chemother. 2017 Oct 9. pii:
AAC.01461-17. doi: 10.1128/AAC.01461-17. [Epub ahead of print] PubMed PMID:
28993337.

2: Khan AM, Shawon J, Halim MA. Multiple receptor conformers based molecular
docking study of fluorine enhanced ethionamide with mycobacterium enoyl ACP
reductase (InhA). J Mol Graph Model. 2017 Sep 14;77:386-398. doi:
10.1016/j.jmgm.2017.09.010. [Epub ahead of print] PubMed PMID: 28957755.

3: Debnath SK, Saisivam S, Omri A. PLGA Ethionamide Nanoparticles for Pulmonary
Delivery: Development and in vivo evaluation of dry powder inhaler. J Pharm
Biomed Anal. 2017 Oct 25;145:854-859. doi: 10.1016/j.jpba.2017.07.051. Epub 2017
Aug 9. PubMed PMID: 28826144.

4: Zhang HN, Xu ZW, Jiang HW, Wu FL, He X, Liu Y, Guo SJ, Li Y, Bi LJ, Deng JY,
Zhang XE, Tao SC. Cyclic di-GMP regulates Mycobacterium tuberculosis resistance
to ethionamide. Sci Rep. 2017 Jul 19;7(1):5860. doi: 10.1038/s41598-017-06289-7.
PubMed PMID: 28725053; PubMed Central PMCID: PMC5517500.

5: Costa-Gouveia J, Pancani E, Jouny S, Machelart A, Delorme V, Salzano G,
Iantomasi R, Piveteau C, Queval CJ, Song OR, Flipo M, Deprez B, Saint-André JP,
Hureaux J, Majlessi L, Willand N, Baulard A, Brodin P, Gref R. Combination
therapy for tuberculosis treatment: pulmonary administration of ethionamide and
booster co-loaded nanoparticles. Sci Rep. 2017 Jul 14;7(1):5390. doi:
10.1038/s41598-017-05453-3. PubMed PMID: 28710351; PubMed Central PMCID:
PMC5511234.

6: Qamar S, Farooqi JQ, Jabeen K, Hasan R. Phenotypic low-level isoniazid
resistance as a marker to predict ethionamide resistance in Mycobacterium
tuberculosis. Int J Mycobacteriol. 2017 Apr-Jun;6(2):167-170. doi:
10.4103/ijmy.ijmy_34_17. PubMed PMID: 28559519.

7: Wankar J, Salzano G, Pancani E, Benkovics G, Malanga M, Manoli F, Gref R,
Fenyvesi E, Manet I. Efficient loading of ethionamide in cyclodextrin-based
carriers offers enhanced solubility and inhibition of drug crystallization. Int J
Pharm. 2017 Oct 15;531(2):568-576. doi: 10.1016/j.ijpharm.2017.05.041. Epub 2017
May 22. PubMed PMID: 28546070.

8: Ang MLT, Zainul Rahim SZ, de Sessions PF, Lin W, Koh V, Pethe K, Hibberd ML,
Alonso S. EthA/R-Independent Killing of Mycobacterium tuberculosis by
Ethionamide. Front Microbiol. 2017 Apr 25;8:710. doi: 10.3389/fmicb.2017.00710.
eCollection 2017. PubMed PMID: 28487681; PubMed Central PMCID: PMC5403819.

9: Nikiforov PO, Blaszczyk M, Surade S, Boshoff HI, Sajid A, Delorme V, Deboosere
N, Brodin P, Baulard AR, Barry CE 3rd, Blundell TL, Abell C. Fragment-Sized EthR
Inhibitors Exhibit Exceptionally Strong Ethionamide Boosting Effect in Whole-Cell
Mycobacterium tuberculosis Assays. ACS Chem Biol. 2017 May 19;12(5):1390-1396.
doi: 10.1021/acschembio.7b00091. Epub 2017 Apr 5. PubMed PMID: 28314097; PubMed
Central PMCID: PMC5474694.

10: Vale N, Correia A, Silva S, Figueiredo P, Mäkilä E, Salonen J, Hirvonen J,
Pedrosa J, Santos HA, Fraga A. Preparation and biological evaluation of
ethionamide-mesoporous silicon nanoparticles against Mycobacterium tuberculosis.
Bioorg Med Chem Lett. 2017 Feb 1;27(3):403-405. doi: 10.1016/j.bmcl.2016.12.060.
Epub 2016 Dec 26. PubMed PMID: 28057421.