Thiamphenicol
Thiamphenicol
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Thiamphenicol

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Catalog Number PR15318453
CAS 15318-45-3
Structure
Description Thiamphenicol is a sulfone and a monocarboxylic acid amide. It has a role as an immunosuppressive agent and an antimicrobial agent.
Synonyms Thiophenicol; Raceophenidol; (+)-Thiamphenicol
IUPAC Name 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
Molecular Weight 356.2
Molecular Formula C12H15Cl2NO5S
InChI OTVAEFIXJLOWRX-NXEZZACHSA-N
InChI Key InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1
Drug Categories Alcohols; Amphenicols; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; Benzene Derivatives; Glycols; Nitro Compounds; Nitrobenzenes; Propylene Glycols
Drug Interactions Acenocoumarol-The risk or severity of bleeding can be increased when Thiamphenicol is combined with Acenocoumarol.
Ambroxol-The risk or severity of methemoglobinemia can be increased when Thiamphenicol is combined with Ambroxol.
Articaine-The risk or severity of methemoglobinemia can be increased when Thiamphenicol is combined with Articaine.
BCG vaccine-The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Thiamphenicol.
Benzocaine-The risk or severity of methemoglobinemia can be increased when Thiamphenicol is combined with Benzocaine.
Isomeric SMILES CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
Type Small Molecule
Therapeutic Category Antibacterials
Pharmacology

Mechanism of Action

Thiamphenicol is a broad-spectrum antibiotic that functions by inhibiting bacterial protein synthesis. It achieves this by binding to the 50S subunit of the bacterial ribosome, thereby preventing the translocation of peptidyl-tRNA from the A site to the P site. This action effectively hinders the growth and reproduction of bacterial cells. The effectiveness of Thiamphenicol in targeting Escherichia coli is attributed to its ability to disrupt essential cellular mechanisms, thereby mitigating bacterial infection.

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