sparfloxacin   Click here for help

GtoPdb Ligand ID: 10860

Synonyms: AT-4140 | AT4140 | CI-978 | CI978 | SPFX | Zagam ®
Approved drug
sparfloxacin is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Sparfloxacin is a fluoroquinolone antibacterial. It has a less than ideal side-effect profile [3] that led to its withdrawl from the US market.

sparfloxacin 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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Click here for structure editor
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 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 100.59
Molecular weight 392.17
XLogP 4.1
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 C[C@@H]1N[C@H](C)CN(C1)c1c(F)c(N)c2c(c1F)n(cc(c2=O)C(=O)O)C1CC1
Isomeric SMILES C[C@@H]1N[C@H](C)CN(C1)c1c(F)c(N)c2c(c1F)n(cc(c2=O)C(=O)O)C1CC1
InChI InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+
InChI Key DZZWHBIBMUVIIW-DTORHVGOSA-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. Domagala JM, Bridges AJ, Culbertson TP, Gambino L, Hagen SE, Karrick G, Porter K, Sanchez JP, Sesnie JA, Spense FG et al.. (1991)
Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship.
J Med Chem, 34 (3): 1142-54. [PMID:1848296]
2. Ohtsuka M, Kikuchi K, Shimizu K, Takahashi N, Ono Y, Sasaki T, Hiramatsu K. (2009)
Emergence of quinolone-resistant Bordetella pertussis in Japan.
Antimicrob Agents Chemother, 53 (7): 3147-9. [PMID:19414571]
3. Psaty BM. (2008)
Clinical trial design and selected drug safety issues for antibiotics used to treat community-acquired pneumonia.
Clin Infect Dis, 47 Suppl 3: S176-9. [PMID:18986285]