OPS-2071   Click here for help

GtoPdb Ligand ID: 13197

Compound class: Synthetic organic
Comment: OPS-2071 is a fluoroquinolone antibacterial compound, with broad-spectrum activity against both Gram-positive and Gram-negative bacteria [2]. It is a clinical candidate being developed by Otsuka Pharmaceutical (Tokyo, Japan) as a treatment for intestinal infections, particularly those caused by Clostridioides difficile. Functionally, it is a type II DNA topoisomerase inhibitor with similar activity against DNA gyrase and DNA topoisomerase 4 [1].
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 CDK toolkit. 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 119.78
Molecular weight 378.36
XLogP 0.95
No. Lipinski's rules broken 0
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.

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Canonical SMILES CC1=C2C(=CC(=C1C3=CC(=C(N)N=C3)C#N)F)C(=O)C(=CN2C4CC4)C(=O)O
Isomeric SMILES N#CC=1C=C(C=NC1N)C2=C(F)C=C3C(=O)C(=CN(C3=C2C)C4CC4)C(=O)O
InChI InChI=1S/C20H15FN4O3/c1-9-16(11-4-10(6-22)19(23)24-7-11)15(21)5-13-17(9)25(12-2-3-12)8-14(18(13)26)20(27)28/h4-5,7-8,12H,2-3H2,1H3,(H2,23,24)(H,27,28)
InChI Key DTSKYQBTFHFYAZ-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
The therapeutic effects of OPS-2071 are mainly confined to the gastrointestinal tract, due to low oral absorption, and this may help to minimize the side effects associated with quinolones [2]. A Phase 2 study to evaluate safety, efficacy and pharmacokinetics of OPS-2071 in patients with bacterial enteritis caused by Clostridium difficile infection (NCT02473393) has been completed and recruitment has commenced for a trial to assess safety and efficacy of the drug in the treatment of irritable bowel syndrome of diarrhoea type (NCT05923892). A further trial to study safety and efficacy in patients with Crohn's Disease (NCT03850509) was terminated by the sponsor.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03850509 Efficacy and Safety of Oral OPS-2071 in Participants With Crohn's Disease Showing Symptoms of Active Inflammation Phase 2 Interventional Otsuka Pharmaceutical Development & Commercialization, Inc.
NCT05923892 Phase II Clinical Trial of OPS-2071 in the Treatment of Irritable Bowel Syndrome of Diarrhea Type Phase 2 Interventional Otsuka Beijing Research Institute
NCT02473393 A Clinical Trial to Assess Three Different Doses of OPS-2071 in Patients With Bacterial Enteritis Phase 2 Interventional Otsuka Pharmaceutical Co., Ltd.