Compound ID | 1991

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Tevenel

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 fluorinated derivative of thiamphenicol. Used in veterinary medicine
Year first mentioned: 1975
Development status: Experimental
Reason dropped: Strong inhibitor of mitochondrial protein synthesis
Chemical structure(s):
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Molecular weight: 357.21
Iso. SMILES: C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)S(=O)(=O)N
InChI Key: HODRFAVLXIFVTR-RKDXNWHRSA-N
Can. SMILES: C1=C(C=CC(=C1)S(=O)(=O)N)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
InChI: InChI=1S/C11H14Cl2N2O5S/c12-10(13)11(18)15-8(5-16)9(17)6-1-3-7(4-2-6)21(14,19)20/h1-4,8-10,16-17H,5H2,(H,15,18)(H2,14,19,20)/t8-,9-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/160746
Guide to Pharmacology: tevenel
Citations:
  • https://febs.onlinelibrary.wiley.com/doi/full/10.1111/j.1432-1033.1987.tb10991.x?sid=nlm%3Apubmed
  • https://www.sciencedirect.com/science/article/abs/pii/000398619290078B

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