CAS Number |
15318-45-3 |
Molecular Formula |
C12H15Cl2NO5S
|
Molecular Weight |
356.22 g/mol |
Form |
Powder |
Appearance |
Off-white powder |
Purity Level |
≥98.0% |
Solubility |
Acetonitrile: Soluble
Alcohol: Soluble
Dimethylacetamide: Soluble
Dimethylformamide: Soluble
Water: Slightly soluble |
Source |
Synthetic |
Absorbance |
UV max (95% ethanol): 224, 266, 274 nm (ε 13,700, 800, 700). |
Boiling Point |
695.9 °C |
Melting Point |
164.3-166.3 °C |
Flash Point |
374.7 °C |
Storage Conditions |
2-8 °C, protect from light |
Description
Thiamphenicol is a bacteriostatic antibiotic derived from chloramphenicol. Like chloramphenicol, thiamphenicol is insoluble in water but highly soluble in lipids.
Mechanism
Both thiamphenicol and chloramphenicol work by the same mechanism, however, thiamphenicol is about 3X as potent. After entering a bacterial cell, thiamphenicol binds to the 50S ribosomal subunit preventing peptide bond formation. Resistance to thiamphenicol may be due to decreased cell permeability or a mutation in the 50S ribosomal subunit.
Spectrum
Thiamphenicol is a broad spectrum antibiotic commonly used to target bacteria responsible for causing sexually transmitted diseases.
-
Microbiology Applications
Thiamphenicol is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against gram positive and gram negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Representative MIC values include:
- Neisseria gonorrhoeae 0.125 µg/mL – 4 µg/mL
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Plant Biology Applications
In a study by Meynier et al. (1989), thiamphenicol was used for hygienic purposes in hybrid walnut propagation. In addition to other antibiotics used during the study, thiamphenicol was found to be effective against several gram negative pathogenic bacteria.