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
SMILES / InChI / InChIKey
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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)
InChI Key CAOTVXGYTWCKQE-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)adamantane-1-carboxamide
International Nonproprietary Names Click here for help
INN number INN
10561 opaganib
Synonyms Click here for help
ABC 294640 | ABC-294640 | Yeliva®
Database Links Click here for help
CAS Registry No. 915385-81-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL2158685
GtoPdb PubChem SID 178103237
PubChem CID 15604015
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