opaganib   Click here for help

GtoPdb Ligand ID: 6624

Synonyms: ABC 294640 | ABC-294640 | Yeliva®
Compound class: Synthetic organic
Comment: Opaganib (ABC294640) is an orally bioavailable sphingosine kinase 2-selective inhibitor that is being investigated for clinical antiproliferative efficacy in various cancers [3]. The sphingosine kinases (SK1 and SK2) are key enzymes within the sphingolipid metabolism pathway that promote tumour growth and pathologic inflammation. Opaganib is being developed by RedHill Bio. In 2017 the FDA granted this compound orphan designation for the treatment of cholangiocarcinoma.

SARS-CoV-2 and COVID-19: A medRxiv preprint descibes the compassionate use of opaganib in a small cohort of patients with severe COVID-19 [2], predicated upon the drug's anti-inflammatory and anti-viral properties. The analysis indicated trends in favour of clinical efficacy which led to extended investigation in a Phase 2 randomised placebo-controlled trial.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 41.99
Molecular weight 380.17
XLogP 5.03
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc(cc1)C12CC3CC(C1)CC(C2)(C3)C(=O)NCc1ccncc1
Isomeric SMILES Clc1ccc(cc1)C12CC3CC(C1)CC(C2)(C3)C(=O)NCc1ccncc1
InChI InChI=1S/C23H25ClN2O/c24-20-3-1-19(2-4-20)22-10-17-9-18(11-22)13-23(12-17,15-22)21(27)26-14-16-5-7-25-8-6-16/h1-8,17-18H,9-15H2,(H,26,27)
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Summary of Clinical Use Click here for help
ABC294640 has advanced to clinical evaluation in patients with advanced cholangiocarcinoma, advanced hepatocellular carcinoma and refractory/relapsed multiple myeloma (to view ClinicalTrials.gov's list of ABC294640 trials click here).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04414618 A Study of Opaganib in Coronavirus Disease 2019 Pneumonia Phase 2 Interventional RedHill Biopharma Limited
NCT03377179 A Study of ABC294640 (Yeliva ®) Alone and in Combination With Hydroxychloroquine Sulfate in Treatment of Patients With Advanced Cholangiocarcinoma Phase 2 Interventional RedHill Biopharma Limited 2
NCT04435106 Compassionate Use of Opaganib in Patients With Coronavirus Disease 2019 (COVID-19) Observational Shaare Zedek Medical Center Results analysis indicated trends in favour of clinical efficacy, along with favourable safety, which led to extended investigation in a Phase 2 randomised placebo-controlled trial in patients with COVID-19 pneumonia. 2