acebilustat   Click here for help

GtoPdb Ligand ID: 11984

Synonyms: CTX-4430 | CTX4430
PDB Ligand
Compound class: Synthetic organic
Comment: Acebilustat (CTX-4430) is an oral leukotriene A4 hydrolase (LTA4H) inhibitor. Pharmacokinetic data indicate that it's suitable for one-daily administration. Acebilustat disrupts biosynthesis of the pro-inflammatory mediator leukotriene B4 (which is a chemoattractant and activator of inflammatory immune cells such as neutrophils), and thus has anti-inflammatory activity.
The chemical structure is claimed in Celtaxsys' patent WO2014164658A1 [2].

Acebilustat is under investigation for clinical utility as an inhibitor of COVID-19 inflammation.
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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
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 5
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 79.04
Molecular weight 481.2
XLogP 4.23
No. Lipinski's rules broken 0

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 OC(=O)c1ccc(cc1)CN1C[C@@H]2C[C@H]1CN2Cc1ccc(cc1)Oc1ccc(cc1)c1ncco1
Isomeric SMILES C1[C@H]2CN([C@@H]1CN2Cc1ccc(cc1)Oc1ccc(cc1)c1ncco1)Cc1ccc(cc1)C(=O)O
InChI InChI=1S/C29H27N3O4/c33-29(34)23-5-1-20(2-6-23)16-31-18-25-15-24(31)19-32(25)17-21-3-9-26(10-4-21)36-27-11-7-22(8-12-27)28-30-13-14-35-28/h1-14,24-25H,15-19H2,(H,33,34)/t24-,25-/m0/s1
InChI Key GERJIEKMNDGSCS-DQEYMECFSA-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
Acebilustat (CTX-4430) has been evaluated for clinical anti-inflammatory activity in lung inflammation (including in cystic fibrosis patients) and in acne vulgaris. The EMA and FDA granted orphan designation as a treatment for cystic fibrosis in 2014 and 2015 respectively.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04662086 COVID-19 Outpatient Pragmatic Platform Study (COPPS) - Master Protocol Phase 2 Interventional Stanford University
NCT05203835 Trial of Acebilustat for the Treatment of Upper Arm Lymphedema Phase 2 Interventional Stanford University
NCT02385760 CTX-4430 for the Treatment of Moderate to Severe Facial Acne Vulgaris Phase 2 Interventional Celtaxsys, Inc.
NCT02443688 EMPIRE CF: A Phase 2 Study to Evaluate the Efficacy, Safety, and Tolerability of CTX-4430 in Adult Cystic Fibrosis (CF) Patients Phase 2 Interventional Celtaxsys, Inc. Acebilustat did not improve lung function in CF patients in this study. Results suggest that it may be of some benefit in patients in earlier stages of lung disease, but further assessment would be required to confirm this. 1