rufloxacin   Click here for help

GtoPdb Ligand ID: 12473

Synonyms: MF 934 | Monos®
Approved drug
rufloxacin is an approved drug
Compound class: Synthetic organic
Comment: Rufloxacin is a fluoroquinolone antibacterial compound, with broad-spectrum activity against both Gram-positive and Gram-negative bacteria [1].
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 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.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 89.39
Molecular weight 363.41
XLogP 1.93
No. Lipinski's rules broken 0
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.

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Canonical SMILES CN1CCN(CC1)C2=C3C4=C(C=C2F)C(=O)C(=CN4CCS3)C(=O)O
Isomeric SMILES CN1CCN(CC1)C2=C(C=C3C4=C2SCCN4C=C(C3=O)C(=O)O)F
InChI InChI=1S/C17H18FN3O3S/c1-19-2-4-20(5-3-19)14-12(18)8-10-13-16(14)25-7-6-21(13)9-11(15(10)22)17(23)24/h8-9H,2-7H2,1H3,(H,23,24)
InChI Key NJCJBUHJQLFDSW-UHFFFAOYSA-N
References
1. Cecchetti V, Fravolini A, Fringuelli R, Mascellani G, Pagella P, Palmioli M, Segre G, Terni P. (1987)
Quinolonecarboxylic acids. 2. Synthesis and antibacterial evaluation of 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids.
J Med Chem, 30 (3): 465-73. [PMID:3820216]
2. European Medicines Agency. 
Quinolone- and fluoroquinolone-containing medicinal products.
Accessed on 16/03/2023. Modified on 16/03/2023. https://www.ema.europa.eu/en/medicines/human/referrals/quinolone-fluoroquinolone-containing-medicinal-products
3. US Food and Drug Administration. 
Fluoroquinolone Antimicrobial Drugs Information.
Accessed on 16/03/2023. Modified on 16/03/2023. https://www.fda.gov/drugs/information-drug-class/fluoroquinolone-antimicrobial-drugs-information