trovafloxacin   Click here for help

GtoPdb Ligand ID: 13476

Synonyms: CP-99,219 | Trovan® | Turvel®
Approved drug
trovafloxacin is an approved drug (FDA (1997), EMA (1998))
Compound class: Synthetic organic
Comment: Trovafloxacin is a 1,8-naphthyridine derivative, structurally related to the fluoroquinolones. It is a type II DNA topoisomerase inhibitor and has broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria [1-3]. Note that structure shown here matches the PubChem standardized chemical structure. There are varying representations of its stereochemistry across other databases.

trovafloxacin 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 7
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 99.23
Molecular weight 416.35
XLogP 1.39
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 C1=C(C=C(C(=C1)N2C=C(C(=O)C3=C2N=C(C(=C3)F)N4C[C@H]5[C@@H](C4)C5N)C(=O)O)F)F
Isomeric SMILES C1[C@@H]2[C@@H](C2N)CN1C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F
InChI InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16?
InChI Key WVPSKSLAZQPAKQ-SOSAQKQKSA-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/)
No information available.
Summary of Clinical Use Click here for help
Trovafloxacin mesylate was granted approval by the US FDA in 1997 (sold as Trovan® tablets) but has since been discontinued. In 1998, the EMA granted Europe-wide approval for the use of this drug (marketed as Trovan® and Turvel®), but this was withdrawn in 1999 following reports of hepatotoxicity. Trovafloxacin was indicated for use in the treatment of pneumonia, acute exacerbations of chronic bronchitis, acute sinusitis, complicated intra-abdominal infections, acute pelvic and gynaecological infections, and skin and soft tissue infections.