razuprotafib   Click here for help

GtoPdb Ligand ID: 11336

Synonyms: AKB-9778 | AKB9778 | Compound AA34 [US10220048]
Compound class: Synthetic organic
Comment: Razuprotafib (AKB-9778) is an inhibitor of protein tyrosine phosphatase receptor type B (PTPRB). It functions to activate Tie2 and this activity blocks neovascularisation [2].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

razuprotafib is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 10
Hydrogen bond donors 4
Rotatable bonds 14
Topological polar surface area 211.58
Molecular weight 586.1
XLogP 2.55
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)N[C@H](C(=O)N[C@H](c1csc(n1)c1cccs1)Cc1ccc(cc1)NS(=O)(=O)O)Cc1ccccc1
Isomeric SMILES COC(=O)N[C@H](C(=O)N[C@H](c1csc(n1)c1cccs1)Cc1ccc(cc1)NS(=O)(=O)O)Cc1ccccc1
InChI InChI=1S/C26H26N4O6S3/c1-36-26(32)29-21(15-17-6-3-2-4-7-17)24(31)27-20(22-16-38-25(28-22)23-8-5-13-37-23)14-18-9-11-19(12-10-18)30-39(33,34)35/h2-13,16,20-21,30H,14-15H2,1H3,(H,27,31)(H,29,32)(H,33,34,35)/t20-,21-/m0/s1
InChI Key KWJDHELCGJFUHW-SFTDATJTSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Razuprotafib (AKB-9778) was originally advanced to clinical trials as a potential treatment for opthalmic vascularisation disorders.
SARS-CoV-2 and COVID-19: In Phase 2 evaluation as a mechanism to combat vascular leak in ARDS in severe COVID-19.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04284514 Study to Evaluate the Safety, Tolerability, Pharmacokinetics and Pharmacodynamics of AKB-9778 Ophthalmic Solution Phase 1 Interventional Aerpio Therapeutics
NCT04405245 Study to Assess the Efficacy, Safety and Tolerability of AKB-9778 Ophthalmic Solution as and Adjunct to Latanoprost in Patients With Ocular Hypertension or Open Angle Glaucoma Phase 2 Interventional Aerpio Therapeutics
NCT03197870 The TIME-2b Study: A Study of AKB-9778, a Novel Tie 2 Activator, in Patients With Non-Proliferative Diabetic Retinopathy (NPDR) Phase 2 Interventional Aerpio Therapeutics
NCT02050828 The TIME-2 Study: A Phase 2 Study of AKB-9778, a Novel Tie-2 Activator, in Patients With Diabetic Macular Edema Phase 2 Interventional Aerpio Therapeutics
NCT04511650 A Study to Evaluate the Safety and Efficacy of Razuprotafib, a Novel Tie 2 Activator, in Hospitalized Subjects With Moderate to Severe Coronavirus Disease 2019 (COVID-19) Phase 2 Interventional Aerpio Therapeutics
NCT04488081 I-SPY COVID-19 TRIAL: An Adaptive Platform Trial for Critically Ill Patients Phase 2 Interventional QuantumLeap Healthcare Collaborative