Compound ID | 1989

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Chloramphenicol

Synonym(s): Chloromycetin

Class: Phenicol

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Binds to the 23S rRNA of the 50S ribosomal subunit and inhibits the peptidyl transferase activity of the bacterial ribosome, thus preventing protein chain elongation. It is active against Gram-positive and Gram-negative bacteria.
Description: Natural product produced by Streptomyces, synthetic production. Systemic and topical application.
Year first mentioned: 1947
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 323.13
Iso. SMILES: C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
InChI Key: WIIZWVCIJKGZOK-RKDXNWHRSA-N
Can. SMILES: C1=C(C=CC(=C1)[N+](=O)[O-])[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
InChI: InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5959
Guide to Pharmacology: chloramphenicol
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/25583746/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4929435/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8066525/
  • https://academic.oup.com/femsre/article/28/5/519/776258

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