ciprofloxacin   Click here for help

GtoPdb Ligand ID: 10902

Synonyms: BAY-O-9867 | BAY-O9867 | Cetraxal® | Ciloxan® | Cipro® | CPFX | Proquin XR
Approved drug PDB Ligand
ciprofloxacin is an approved drug (FDA (1987))
Compound class: Synthetic organic
Comment: Ciprofloxacin is a synthetic, broad spectrum second generation fluoroquinolone antibacterial.

ciprofloxacin 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 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 74.57
Molecular weight 331.13
XLogP 3.84
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 Fc1cc2c(cc1N1CCNCC1)n(cc(c2=O)C(=O)O)C1CC1
Isomeric SMILES Fc1cc2c(cc1N1CCNCC1)n(cc(c2=O)C(=O)O)C1CC1
InChI InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
InChI Key MYSWGUAQZAJSOK-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/)
Bioactivity Comments
The MIC90 for antibacterial activity against ciprofloxacin-susceptible Haemophilus influenzae is 8 ng/ml in vitro [2].
Targets where the ligand is described in the comment field
Target Comment
DNA gyrase DNA gyrase is a type II DNA topoisomerase [1] and one of two enzymes of this subclass found in bacteria, the other being DNA topoisomerase 4. DNA gyrase introduces negative supercoils in closed circular double-stranded DNA in an ATP-dependent manner.
This enzyme is the clinically-validated target for a number of antibacterial drug classes, including the aminocoumarins such as novobiocin and fluoroquinolones such as moxifloxacin, levofloxacin, ciprofloxacin and ofloxacin.