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Azidamfenicol (CAS 13838-08-9)

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Alternate Names:
Azidoamphenicol; Leukomycin N
Application:
Azidamfenicol is a semi-synthetic chloramphenicol
CAS Number:
13838-08-9
Purity:
≥95%
Molecular Weight:
295.25
Molecular Formula:
C11H13N5O5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Azidamfenicol, cataloged under the CAS number 13838-08-9, is a chemically modified analog of the antibiotic chloramphenicol, distinguished by the substitution of an azido group for the hydroxyl group in the dichloroacetic side chain. This modification imparts unique properties to the molecule, primarily affecting its interaction with bacterial ribosomes. Azidamfenicol operates by binding to the 50S subunit of the bacterial ribosome, a critical component in the protein synthesis machinery of bacteria. Its binding inhibits peptidyl transferase, an enzyme necessary for the formation of peptide bonds between amino acids, effectively halting the elongation of the protein chain. This action disrupts protein synthesis, leading to the cessation of bacterial growth. In research environments, azidamfenicol has been utilized to explore the dynamics of ribosomal inhibition and the structural requirements for binding efficiency and specificity to the ribosome. Studies involving azidamfenicol have provided deeper insights into the mechanistic pathways of ribosomal interference by antibiotics and have aided in understanding how chemical modifications can enhance or alter the activity of antibiotic molecules. This research has implications for designing antibiotics with improved efficacy and understanding resistance mechanisms at a molecular level.


Azidamfenicol (CAS 13838-08-9) References

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  2. Azide: a unique dipole for metal-free bioorthogonal ligations.  |  Debets, MF., et al. 2010. Chembiochem. 11: 1168-84. PMID: 20455238
  3. Derivative spectrophotometric determination of clotrimazole in single formulations and in combination with other drugs.  |  Bedair, MM., et al. 1989. J Assoc Off Anal Chem. 72: 432-5. PMID: 2745365
  4. The prototypical proton-coupled oligopeptide transporter YdgR from Escherichia coli facilitates chloramphenicol uptake into bacterial cells.  |  Prabhala, BK., et al. 2018. J Biol Chem. 293: 1007-1017. PMID: 29150447
  5. Bacterial Dehydrogenases Facilitate Oxidative Inactivation and Bioremediation of Chloramphenicol.  |  Zhang, L., et al. 2023. Chembiochem. 24: e202200632. PMID: 36353978
  6. Old Antibiotics Can Learn New Ways: A Systematic Review of Florfenicol Use in Veterinary Medicine and Future Perspectives Using Nanotechnology.  |  Trif, E., et al. 2023. Animals (Basel). 13: PMID: 37238125
  7. Metabophore-mediated retro-metabolic ('MeMeReMe') approach in drug design.  |  Balaji, S. 2023. Drug Discov Today. 28: 103736. PMID: 37586644
  8. Formulation, pharmacokinetics, and antibacterial activity of florfenicol-loaded niosome.  |  Abonashey, SG., et al. 2024. Drug Deliv Transl Res. 14: 1077-1092. PMID: 37957473
  9. [Determination of antimicrobial activity of a combination of acidamfenicol, clotrimazole and dexamethasone in vitro (author's transl)].  |  Poitschek, C., et al. 1978. Arzneimittelforschung. 28: 232-4. PMID: 580383
  10. ESIPT-based highly selective fluorescent probe for organic azides through Staudinger ligation.  |  Peng and Fangfang, et al. 2018. Journal of Photochemistry and Photobiology A: Chemistry. 355: 180-185.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Azidamfenicol, 5 mg

sc-391749
5 mg
$270.00