rosoxacin   Click here for help

GtoPdb Ligand ID: 12474

Synonyms: acrosoxacin | Eracine® | Eradacil® | Eradacin® | WIN 35213 | Winuron®
Approved drug
rosoxacin is an approved drug
Compound class: Synthetic organic
Comment: Rosoxacin is a quinolone antibacterial compound with activity against Gram-negative bacteria.

rosoxacin is commercially available from our sponsors

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 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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 69.97
Molecular weight 294.31
XLogP 1.44
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
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.

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/)

✖
Canonical SMILES CCN1C=C(C(=O)C2=CC=C(C=C21)C3=CC=NC=C3)C(=O)O
Isomeric SMILES CCN1C=C(C(=O)C2=C1C=C(C=C2)C3=CC=NC=C3)C(=O)O
InChI InChI=1S/C17H14N2O3/c1-2-19-10-14(17(21)22)16(20)13-4-3-12(9-15(13)19)11-5-7-18-8-6-11/h3-10H,2H2,1H3,(H,21,22)
InChI Key XBPZXDSZHPDXQU-UHFFFAOYSA-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/)
References
1. Dobson RA, O'Connor JR, Poulin SA, Kundsin RB, Smith TF, Came PE. (1980)
In vitro antimicrobial activity of rosoxacin against Neisseria gonorrhoeae, Chlamydia trachomatis, and Ureaplasma urealyticum.
Antimicrob Agents Chemother, 18 (5): 738-40. [PMID:6778385]
2. European Medicines Agency. 
Fluoroquinolone and quinolone antibiotics: PRAC recommends restrictions on use.
Accessed on 16/03/2023. Modified on 16/03/2023. https://www.ema.europa.eu/en/documents/press-release/fluoroquinolone-quinolone-antibiotics-prac-recommends-restrictions-use_en.pdf