Compound ID | 1992

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Thiamphenicol

Synonym(s): Propacin

Class: Phenicol

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to the 23S rRNA of the bacterial 50S ribosomal subunit to inhibit peptidyl transferase activity, thus preventing protein chain elongation
Description: Synthetic derivative of chloramphenicol
Year first mentioned: 1959
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 356.22
Iso. SMILES: CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
InChI Key: OTVAEFIXJLOWRX-NXEZZACHSA-N
Can. SMILES: CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/27200
Guide to Pharmacology: thiamphenicol
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/7036847/
  • https://febs.onlinelibrary.wiley.com/doi/full/10.1111/j.1432-1033.1987.tb10991.x?sid=nlm%3Apubmed

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