fluorothiazinon   Click here for help

GtoPdb Ligand ID: 13810

Synonyms: CL-55 | fluorothiazinone | Ftortiazinon
Compound class: Synthetic organic
Comment: Fluorothiazinon is a clinical stage thiohydrazide compound with promising anti-virulence activity against Gram-negative bacteria [3,5,7]. Functionally it is an inhibitor of the type III secretion system (T3SS) [7], one of the main pathogenicity factors of Gram-negative bacteria [2].
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 7
Topological polar surface area 116.53
Molecular weight 421.42
XLogP 1.22
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 CCOC1=CC(=CC=C1O)CN2C(=O)CSC(=N2)C(=O)NC3=CC=C(C=C3F)F
Isomeric SMILES CCOC1=C(C=CC(=C1)CN2C(=O)CSC(=N2)C(=O)NC3=C(C=C(C=C3)F)F)O
InChI InChI=1S/C19H17F2N3O4S/c1-2-28-16-7-11(3-6-15(16)25)9-24-17(26)10-29-19(23-24)18(27)22-14-5-4-12(20)8-13(14)21/h3-8,25H,2,9-10H2,1H3,(H,22,27)
InChI Key DAKWAZGLXWXDBB-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/)
No information available.
Summary of Clinical Use Click here for help
Fluorothiazinon has progressed to Phase 2 clinical evaluation for the treatment of complicated urinary tract infections (cUTIs), with positive results published in 2024 (NCT03638830; [6]). A second study (NCT06135350) will evaluate the prevention of ventilator-associated bacterial pneumonia (VAP) using fluorothiazinon as a monotherapy (not yet recruiting, last update March 2025).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT06135350 Clinical Trial to Study the Efficacy and Safety of Fluorothiazinone (N.F. Gamaleya NRCEM) in Prophylaxis of Nosocomial Bacterial Infections With Participation of Patients on MV Phase 2 Interventional Gamaleya Research Institute of Epidemiology and Microbiology, Health Ministry of the Russian Federation
NCT03638830 Safety and Efficacy Study of Ftortiazinon in the Treatment of Patients With Complicated Urinary Tract Infections Caused by P. Aeruginosa Phase 2 Interventional Gamaleya Research Institute of Epidemiology and Microbiology, Health Ministry of the Russian Federation Fluorothiazinone demonstrated a favourable safety profile. The study also found that fluorothiazinone + cefepime showed superior efficacy compared to cefepime alone in patients with cUTIs. 6