Compound ID | 1989

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Chloramphenicol

Synonym(s): Chloromycetin

Class: Phenicol

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to 50S ribosomal subunit inhibiting the attachment of transfer RNA to the A site
Target Pathogen: Broad spectrum activity
Description: Natural product from Streptomyces venezuelae; developed for systemic and topical applications; has known adverse effects/toxicity (ex: bone marrow toxicity)
Institute where first reported: Parke, Davis & Company; Yale University
Year first mentioned: 1947
Highest development stage: Approved by FDA in 1949 but with restricted/regulated use
Development status: Approved
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://academic.oup.com/femsre/article/28/5/519/776258
  • https://doi.org/10.1093/jac/dku530
  • https://doi.org/10.1128/jb.55.3.425-448.1948
  • https://doi.org/10.1126/science.106.2757.417

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