auriclosene   Click here for help

GtoPdb Ligand ID: 13417

Synonyms: NVC-422
Compound class: Synthetic organic
Comment: Auriclosene is the clinical lead from a novel class of synthetic analogues of N-chlorotaurine, an antimicrobial and anti-inflammatory oxidant produced by activated human granulocytes and monocytes [1]. It has broad-spectrum activity against Gram-positive and Gram-negative bacteria.
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 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 65.99
Molecular weight 222.09
XLogP 1.05
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 CC(C)(CS(=O)(=O)O)N(Cl)Cl
Isomeric SMILES CC(C)(CS(=O)(=O)O)N(Cl)Cl
InChI InChI=1S/C4H9Cl2NO3S/c1-4(2,7(5)6)3-11(8,9)10/h3H2,1-2H3,(H,8,9,10)
InChI Key QYNRGGHZWCUZLK-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
NovaBay Pharmaceuticals is developing auriclosene as a topical antimicrobial agent with potential to treat dermatological, ophthalmological and urological infections. Auriclosene has completed a number of Phase 2 clinical trials (see table below) and although no update has been posted on ClinicalTrials.gov since December 2015, the drug remains part of NovaBay's program [2].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02130518 Efficacy Study of Auriclosene Irrigation Solution on Urinary Catheter Patency Phase 2 Interventional NovaBay Pharmaceuticals, Inc.
NCT01532336 Efficacy and Safety of NVC-422 in the Treatment of Adenoviral Conjunctivitis Phase 2 Interventional NovaBay Pharmaceuticals, Inc.
NCT00781339 Safety and Efficacy Study of NVC-422 on Bacteriuria in Catheterized Patients Phase 2 Interventional NovaBay Pharmaceuticals, Inc.
NCT01367314 Safety and Efficacy of Topical NVC-422 Gel in Impetigo Phase 2 Interventional NovaBay Pharmaceuticals, Inc.
NCT01243125 Study to Evaluate NVC-422 for Urinary Catheter Blockage and Encrustation Phase 2 Interventional NovaBay Pharmaceuticals, Inc.
NCT01877694 Efficacy and Safety of Auriclosene (NVC-422) in the Treatment of Bacterial Conjunctivitis Phase 2 Interventional NovaBay Pharmaceuticals, Inc.