Opaganib
Identification
- Generic Name
- Opaganib
- DrugBank Accession Number
- DB12764
- Background
Opaganib, also known as ABC294640, is a selective sphingosine kinase-2 (SK2) inhibitor that is orally administered.2 This drug has potential anticancer, anti-inflammatory, and antiviral activities, with potential applications in oncology, inflammation, the gastrointestinal system, and COVID-19.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 380.92
Monoisotopic: 380.1655411 - Chemical Formula
- C23H25ClN2O
- Synonyms
- 4-Pyridinylmethyl 3(4-Chlorophenyl)Adamantine Carboxamide
- 4-Pyridinylmethyl-3-(4-Chlorophenyl) Adamantine Carboxamide
- ABC-294640
- ABC294640
- Opaganib
- Yeliva
- External IDs
- ABC294640
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Opaganib selectively inhibits sphingosine kinase-2 (SK2).2 This inhibition blocks the synthesis of sphingosine 1-phosphate (S1P) and its activities (which includes regulation of fundamental biological processes such as cell proliferation, migration, immune cell trafficking, angiogenesis, immune-modulation, and suppression of innate immune responses from T-cells). This drug has dual anti-inflammatory and antiviral activity targeting a host cell component and is unaffected by viral mutation, contributing to minimization of the likelihood of resistance.1 It is currently being investigated against COVID-19 as it has demonstrated anti-SARS-CoV-2 activity in studies.
Target Actions Organism ASphingosine kinase 2 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Chlorobenzenes
- Alternative Parents
- Pyridines and derivatives / Aryl chlorides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Chlorobenzene / Heteroaromatic compound / Hydrocarbon derivative show 11 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- DRG21OQ517
- CAS number
- 915385-81-8
- InChI Key
- CAOTVXGYTWCKQE-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 3-(4-chlorophenyl)-N-[(pyridin-4-yl)methyl]adamantane-1-carboxamide
- SMILES
- ClC1=CC=C(C=C1)C12CC3CC(CC(C3)(C1)C(=O)NCC1=CC=NC=C1)C2
References
- General References
- External Links
- Human Metabolome Database
- HMDB0247745
- PubChem Compound
- 15604015
- PubChem Substance
- 347828950
- ChemSpider
- 13079494
- BindingDB
- 50393642
- ChEBI
- 124965
- ChEMBL
- CHEMBL2158685
- Wikipedia
- Opaganib
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Active Not Recruiting Treatment Prostate Cancer 1 2 Completed Treatment Cholangiocarcinoma / Extrahepatic Cholangiocarcinoma / Intrahepatic Cholangiocarcinoma / Non-Resectable Cholangiocarcinoma / Perihilar Cholangiocarcinoma 1 2 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Infections, Coronavirus 1 2 Withdrawn Treatment Hepatocellular Carcinoma 1 2, 3 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Pulmonary Infections 1 1 Completed Treatment Pancreatic Cancer / Unspecified Adult Solid Tumor, Protocol Specific 1 1, 2 Terminated Treatment Multiple Myeloma (MM) 1 1, 2 Withdrawn Treatment Coronavirus Disease 2019 (COVID‑19) / Pulmonary Infections 1 1, 2 Withdrawn Treatment Diffuse Large B-Cell Lymphoma (DLBCL) / Kaposi's Sarcoma 1 Not Available Available Not Available Cholangiocarcinoma / Extrahepatic Cholangiocarcinoma / Intrahepatic Cholangiocarcinoma / Non-Resectable Cholangiocarcinoma / Perihilar Cholangiocarcinoma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000215 mg/mL ALOGPS logP 4.56 ALOGPS logP 4.34 Chemaxon logS -6.2 ALOGPS pKa (Strongest Acidic) 15.12 Chemaxon pKa (Strongest Basic) 5.02 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 41.99 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 106.94 m3·mol-1 Chemaxon Polarizability 42.19 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the phosphorylation of sphingosine to form sphingosine-1-phosphate (SPP), a lipid mediator with both intra- and extracellular functions. Also acts on D-erythro-dihydrosphingosine, D-erythro-sphingosine and L-threo-dihydrosphingosine. Binds phosphoinositides (PubMed:19168031, PubMed:12954646). In contrast to prosurvival SPHK1, has a positive effect on intracellular ceramide levels, inhibits cells growth and enhances apoptosis (PubMed:16118219). In mitochondria, is important for cytochrome-c oxidase assembly and mitochondrial respiration. The SPP produced in mitochondria binds PHB2 and modulates the regulation via PHB2 of complex IV assembly and respiration (PubMed:20959514). In nucleus, plays a role in epigenetic regulation of gene expression. Interacts with HDAC1 and HDAC2 and, through SPP production, inhibits their enzymatic activity, preventing the removal of acetyl groups from lysine residues with histones. Upregulates acetylation of histone H3-K9, histone H4-K5 and histone H2B-K12 (PubMed:19729656). In nucleus, may have an inhibitory effect on DNA synthesis and cell cycle (PubMed:12954646, PubMed:16103110). In mast cells, is the main regulator of SPP production which mediates calcium influx, NF-kappa-B activation, cytokine production, such as TNF and IL6, and degranulation of mast cells (By similarity). In dopaminergic neurons, is involved in promoting mitochondrial functions regulating ATP and ROS levels (By similarity). Also involved in the regulation of glucose and lipid metabolism (By similarity).
- Specific Function
- Atp binding
- Gene Name
- SPHK2
- Uniprot ID
- Q9NRA0
- Uniprot Name
- Sphingosine kinase 2
- Molecular Weight
- 69216.375 Da
Drug created at October 21, 2016 00:05 / Updated at December 01, 2022 11:27