Chemical Property of Thiamphenicol
Chemical Property:
- Appearance/Colour:off-white solid
- Melting Point:163-166 °C
- Refractive Index:1.589
- Boiling Point:695.9 °C at 760 mmHg
- PKA:11.05±0.46(Predicted)
- Flash Point:374.7 °C
- PSA：112.08000
- Density:1.491 g/cm3
- LogP:1.87600
- Storage Temp.:-20°C Freezer, Under Inert Atmosphere
- Solubility.:ethanol: 50 mg/mL, clear, colorless
- Water Solubility.:Soluble in acetonitrile or DMF. Slightly soluble in water
- XLogP3:-0.3
- Hydrogen Bond Donor Count:3
- Hydrogen Bond Acceptor Count:5
- Rotatable Bond Count:6
- Exact Mass:355.0047991
- Heavy Atom Count:21
- Complexity:443
- Purity/Quality:
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99.0% *data from raw suppliers
Thiamphenicol *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- Safety Statements:
22-24/25
- MSDS Files:
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SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Chemical Classes:Other Uses -> Pharmaceuticals
- Canonical SMILES:CS(=O)(=O)C1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)O
- Isomeric SMILES:CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
- Recent ClinicalTrials:Effect of Thiamphenicol on EAAT2 and Other Biomarkers From Nasal Biopsied Tissue
- Recent EU Clinical Trials:Efficacy and tollerability of thiamphenicol glycinate acetylcysteinate, given in sequential therapy sistematic and aerosol or by aerosol in the treatment of hight respiratory tract acute infection and/or subacute/recurring clinical study, multicentre, randomized, controlled vs standard therapy
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Description
Thiamphenicol is a broad-spectrum antibiotic chloramphenicol, which is more effective to the gram-negative bacteria than the gram-positive bacteria. At room temperature, it is a white to off-white crystalline powder or crystal, which can be quickly and completely absorped by oral adminstration, as well as it is excreted mainly in the prototype from the urine for metabolism. It is clinically applied for the treatment of respiratory, urinary tract, liver and gallbladder, typhoid and other intestinal surgery, gynecology and ENT infections. Especially in the mild infections it is more effective. It has the similar chemical structure with the chloramphenicol. Its methyl sulfone substituted the nitro of chloramphenicol, which reduced its toxicity, and in vivo its antibacterial activity is 2.5-5 times stronger than chloramphenicol. For gram-positive bacteria, such as streptococcus pneumoniae and hemolytic streptococcus, it has very strong antibacterial effect, while for gram-negative bacteria, such as Neisseria gonorrhoeae, meningococcus, lung Bacteroides, E. coli, Vibrio cholerae, Shigella and influenza bacillus, it also has strong antibacterial effect. For anaerobic bacteria, Rickettsia and amoeba, it has antibacterial effect in some extent. It has the same antimicrobial mechanism with chloramphenicol, which mainly inhibits the synthesis of bacterial protein. This drug is absorped quickly by oral administration, which reaches peak blood concentration within two hours. Its half-life is 5 hours, that is more longer than chloramphenicol. The bacteria have complete cross resistance to it and chloramphenicol, while the bacteria have some cross-resistance phenomenon to it and tetracycline.
Thiamphenicol also has strong immunosuppressive effects, which is an excellent immunosuppressant. Its mechanism of action have significantly different with other immunosuppressive agents. The immunosuppressive effect is several times higher than the chloramphenicol. It can be as the effective extender for transplantation reaction and surgically allogeneic transplantation.
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Uses
It is applied for the treatment of respiratory, urinary tract, liver and gallbladder, typhoid and other intestinal surgery, gynecology and ENT infections. Especially in the mild infections it is more effective. Antimicrobial chelating agent, antiseborrheic Thiamphenicol is an antibiotic. Thiamphenicol is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Thiamphenicol is used particul
arly for the treatment of sexually transmitted infections and pelvic inflammatory disease. Thiamphenicol is a semi-synthetic chloramphenicol prepared by total synthesis from thiophenol in which the nitro moiety of chloramphenicol is replaced by a methylsulphone, first synthesised at Sterling Winthrop in 1952. Thiamphenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Thiamphenicol acts by binding to the 23S sub-unit of the 50S ribosome inhibiting protein synthesis. Thiamphenicol has been extensively studied with over 800 literature citations.
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Therapeutic Function
Antibacterial
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Clinical Use
Similar to that of chloramphenicol.
