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thiamphenicol   Click here for help

GtoPdb Ligand ID: 12400

Synonyms: dextrosulphenidol | thiophenicol
Approved drug PDB Ligand
thiamphenicol is an approved drug
Compound class: Synthetic organic
Comment: Thiamphenicol is a semisynthetic, broad-spectrum antibacterial derived from chloramphenicol.

thiamphenicol is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 112.08
Molecular weight 355
XLogP 0.31
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC[C@H]([C@@H](c1ccc(cc1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl
Isomeric SMILES CS(=O)(=O)c1ccc(cc1)[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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Thiamphenicol is indicated as a treatment for a wide range of bacterial infections, including those of the gastrointestinal, urinary, and respiratory tracts. It has not been associated with aplastic anemia and is therefore considered a safer alternative to chloramphenicol. Thiamphenicol is not FDA approved. In Europe it is not approved at the EMA level, but is/has been approved in a number of national jurisdictions including the Italy, France, Belgium, and Luxembourg.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The amphenicol class of antibacterial compounds prevent protein chain elongation by binding to the 23S rRNA component of the bacterial 50S ribosomal subunit and inhibiting the peptidyl transferase activity of the bacterial ribosome.