Ethionamide

  • CAT Number: A000497
  • CAS Number: 536-33-4
  • Molecular Formula: C8H10N2S
  • Molecular Weight: 166.24
  • Purity: ≥95%
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Ethionamide is a second-line antitubercular agent that inhibits mycolic acid synthesis. Ethionamide is a nicotinamide derivative, with antibacterial activity, used to treat tuberculosis. Although the exact mechanism of action of ethionamide is unknown, it may inhibit the synthesis of mycolic acid, a saturated fatty acid found in the bacterial cell wall, thereby inhibiting bacterial cell wall synthesis. This eventually leads to bacterial cell wall disruption and cell lysis. Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved. It binds with NAD+ to form an adduct.

Catalog Number A000497
CAS Number 536-33-4
Molecular Formula

C8H10N2S

Purity 95%
Target Antibiotic
Solubility >7.7mg/mL in DMSO
Storage -20°C
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
Reference

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transcriptome and genomic analysis of extensively drug-resistant Mycobacterium
tuberculosis clinical isolates identifies downregulation of ethA as a mechanism
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28993337.
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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.
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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
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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.
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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
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PMC5511234.
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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.
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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.
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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.
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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.
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10: Vale N, Correia A, Silva S, Figueiredo P, M&#228;kil&#228; 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.

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