NAV

Opaganib

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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
3D
Similar Structures
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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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ASphingosine kinase 2
inhibitor
Humans
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
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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
  1. RedHill Biopharma: Opaganib - COVID-19 [Link]
  2. Opaganib (Yeliva®, ABC294640) [Link]
Human Metabolome Database
HMDB0247745
PubChem Compound
15604015
PubChem Substance
347828950
ChemSpider
13079494
BindingDB
50393642
ChEBI
124965
ChEMBL
CHEMBL2158685
Wikipedia
Opaganib

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingTreatmentProstate Cancer1
2CompletedTreatmentCholangiocarcinoma / Extrahepatic Cholangiocarcinoma / Intrahepatic Cholangiocarcinoma / Non-Resectable Cholangiocarcinoma / Perihilar Cholangiocarcinoma1
2CompletedTreatmentCoronavirus Disease 2019 (COVID‑19) / Infections, Coronavirus1
2WithdrawnTreatmentHepatocellular Carcinoma1
2, 3CompletedTreatmentCoronavirus Disease 2019 (COVID‑19) / Pulmonary Infections1
1CompletedTreatmentPancreatic Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2TerminatedTreatmentMultiple Myeloma (MM)1
1, 2WithdrawnTreatmentCoronavirus Disease 2019 (COVID‑19) / Pulmonary Infections1
1, 2WithdrawnTreatmentDiffuse Large B-Cell Lymphoma (DLBCL) / Kaposi's Sarcoma1
Not AvailableAvailableNot AvailableCholangiocarcinoma / Extrahepatic Cholangiocarcinoma / Intrahepatic Cholangiocarcinoma / Non-Resectable Cholangiocarcinoma / Perihilar Cholangiocarcinoma1

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
PropertyValueSource
Water Solubility0.000215 mg/mLALOGPS
logP4.56ALOGPS
logP4.34Chemaxon
logS-6.2ALOGPS
pKa (Strongest Acidic)15.12Chemaxon
pKa (Strongest Basic)5.02Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.99 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity106.94 m3·mol-1Chemaxon
Polarizability42.19 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Sphingosine kinase 2
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