azidamfenicol   Click here for help

GtoPdb Ligand ID: 12397

Synonyms: azidamphenicol | azidoamfenicol | azidoamphenicol | Thilocof®
Approved drug
azidamfenicol is an approved drug
Compound class: Synthetic organic
Comment: Azidamfenicol is an analogue of chloramphenicol and classed as an amphenicol antibacterial compound [1].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 125.06
Molecular weight 295.09
XLogP -0.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)CN=[N+]=[N-]
Isomeric SMILES c1cc(ccc1[C@H]([C@@H](CO)NC(=O)CN=[N+]=[N-])O)[N+](=O)[O-]
InChI InChI=1S/C11H13N5O5/c12-15-13-5-10(18)14-9(6-17)11(19)7-1-3-8(4-2-7)16(20)21/h1-4,9,11,17,19H,5-6H2,(H,14,18)/t9-,11-/m1/s1
InChI Key SGRUZFCHLOFYHZ-MWLCHTKSSA-N
No information available.
Summary of Clinical Use Click here for help
Azidamfenicol is used as a topical formulation to treat ocular infections caused by susceptible bacteria. The drug is not approved by the EMA or FDA, but has marketing authorisation in Greece and Cyprus.
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.