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):
Canonical SMILES:	C1=C(C=CC(=C1)[N+](=O)[O-])[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
Isomeric SMILES:	C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[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
InChI Key:	WIIZWVCIJKGZOK-RKDXNWHRSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5959

External links:
Guide to Pharmacology:	chloramphenicol
Main Source:	https://academic.oup.com/femsre/article/28/5/519/776258
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/