Compound ID | 2049

Tosufloxacin

Synonym(s): T-3262

Class: Fluoroquinolone

Spectrum of activity: Gram-negative
Details of activity: Binds to type II topoisomerases, gyrase and topoisomerase IV and thus, inhibits DNA cleavage and ligation reactions. It kills bacterial cells by increasing the concentration of enzyme–DNA cleavage complexes, thereby inhibiting cell replication.
Description: Synthetic 1,8-naphthyridine derivative
Year first mentioned: 1985
Development status: Approved in Japan, off-patent, discontinued in other countries
Reason Dropped: Severe thrombocytopenia, nephritis, hepatotoxicity
Chemical structure(s):
Canonical SMILES: C1=C(C=C(C(=C1)N2C=C(C(=O)C3=C2N=C(C(=C3)F)N4CCC(C4)N)C(=O)O)F)F
Isomeric SMILES: C1CN(CC1N)C2=C(C=C3C(=O)C(=CN(C3=N2)C4=C(C=C(C=C4)F)F)C(=O)O)F
InChI: InChI=1S/C19H15F3N4O3/c20-9-1-2-15(13(21)5-9)26-8-12(19(28)29)16(27)11-6-14(22)18(24-17(11)26)25-4-3-10(23)7-25/h1-2,5-6,8,10H,3-4,7,23H2,(H,28,29)
InChI Key: WUWFMDMBOJLQIV-UHFFFAOYSA-N
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/5517
External links:
Guide to Pharmacology: tosufloxacin
Main Source: https://pubmed.ncbi.nlm.nih.gov/3182417/
Citation: https://pubmed.ncbi.nlm.nih.gov/11549783/

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