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Prothionamide (CAS 14222-60-7)

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Alternate Names:
2-propylpyridine-4-carbothioamide
Application:
Prothionamide is an antibacterial
CAS Number:
14222-60-7
Purity:
≥98%
Molecular Weight:
180.27
Molecular Formula:
C9H12N2S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Prothionamide is a chemical compound that functions as an antibacterial agent in research and development applications. Its mechanism of action involves inhibiting the synthesis of mycolic acids in the cell wall of certain bacteria, specifically Mycobacterium tuberculosis. This disruption of mycolic acid synthesis leads to the impairment of cell wall formation and ultimately the death of the bacterial cells. Prothionamide achieves this by targeting the enzyme InhA, which is involved in the biosynthesis of mycolic acids. By interfering with this specific molecular target, prothionamide disrupts the structural integrity of the bacterial cell wall, rendering the bacteria more susceptible to other antibacterial agents.


Prothionamide (CAS 14222-60-7) References

  1. Hepatitis associated with prothionamide for treatment of multidrug-resistant tuberculosis.  |  Hsu, HL., et al. 2010. J Formos Med Assoc. 109: 923-7. PMID: 21195892
  2. Polymorphisms in isoniazid and prothionamide resistance genes of the Mycobacterium tuberculosis complex.  |  Projahn, M., et al. 2011. Antimicrob Agents Chemother. 55: 4408-11. PMID: 21709103
  3. Ex vivo conversion of prodrug prothionamide to its metabolite prothionamide sulfoxide with different extraction techniques and their estimation in human plasma by LC-MS/MS.  |  Trivedi, V., et al. 2013. Bioanalysis. 5: 185-200. PMID: 23330561
  4. Low Serum Concentrations of Moxifloxacin, Prothionamide, and Cycloserine on Sputum Conversion in Multi-Drug Resistant TB.  |  Lee, SH., et al. 2015. Yonsei Med J. 56: 961-7. PMID: 26069117
  5. Efficacy and tolerability of ethionamide versus prothionamide: a systematic review.  |  Scardigli, A., et al. 2016. Eur Respir J. 48: 946-52. PMID: 27288034
  6. Prothionamide susceptibility testing of Mycobacterium tuberculosis using the resazurin microtitre assay and the BACTECMGIT 960 system.  |  Tan, Y., et al. 2017. Eur J Clin Microbiol Infect Dis. 36: 779-782. PMID: 28000029
  7. Molecular Characterization of Prothionamide-Resistant Mycobacterium tuberculosis Isolates in Southern China.  |  Tan, Y., et al. 2017. Front Microbiol. 8: 2358. PMID: 29250048
  8. Development and evaluation of Chitosan nanoparticles based dry powder inhalation formulations of Prothionamide.  |  Debnath, SK., et al. 2018. PLoS One. 13: e0190976. PMID: 29370192
  9. Mutation EthAW21R confers co-resistance to prothionamide and ethionamide in both Mycobacterium bovis BCG and Mycobacterium tuberculosis H37Rv.  |  Mugweru, J., et al. 2018. Infect Drug Resist. 11: 891-894. PMID: 29942141
  10. Bacterial Genome-Wide Association Identifies Novel Factors That Contribute to Ethionamide and Prothionamide Susceptibility in Mycobacterium tuberculosis.  |  Hicks, ND., et al. 2019. mBio. 10: PMID: 31015328
  11. Development and validation of a simple LC-MS/MS method for simultaneous determination of moxifloxacin, levofloxacin, prothionamide, pyrazinamide and ethambutol in human plasma.  |  Zheng, X., et al. 2020. J Chromatogr B Analyt Technol Biomed Life Sci. 1158: 122397. PMID: 33091676
  12. Identification and characterization of Prothionamide degradation impurities by mass spectrometry, NMR spectroscopy, and ultra high performance liquid chromatography method development.  |  Baksam, VK., et al. 2021. J Sep Sci. 44: 2078-2088. PMID: 33733566
  13. Ethionamide and Prothionamide Based Coumarinyl-Thiazole Derivatives: Synthesis, Antitubercular Activity, Toxicity Investigations and Molecular Docking Studies.  |  Imran, M. 2022. Pharm Chem J. 56: 1215-1225. PMID: 36531826

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Prothionamide, 1 g

sc-204865
1 g
$47.00

Prothionamide, 5 g

sc-204865A
5 g
$92.00

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. The compound, sc-204865, is provided as a yellow crystal or crystalline powder. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-26
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Rated 5 out of 5 by from TrivediTrivedi, V. et al. (PubMed 23330561) examined the ex vivo conversion of prodrug Prothionamide to its metabolite prothionamide sulfoxide using different extraction techniques and estimated their concentration in human plasma by LC-MS/MS. -SCBT Publication Review
Date published: 2015-03-18
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Prothionamide is rated 5.0 out of 5 by 1.
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