Thiamphenicol

Synonym(s): Propacin

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:	Synthetic derivative of chloramphenicol
Year first mentioned:	1959
Development status:	Approved, off-patent, not available in many countries

Chemical structure(s):
Canonical SMILES:	CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
Isomeric 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
InChI Key:	OTVAEFIXJLOWRX-NXEZZACHSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/27200

External links:
Guide to Pharmacology:	thiamphenicol
Main Source:	https://febs.onlinelibrary.wiley.com/doi/full/10.1111/j.1432-1033.1987.tb10991.x?sid=nlm%3Apubmed
Citation:	https://pubmed.ncbi.nlm.nih.gov/7036847/