fruquintinib   Click here for help

GtoPdb Ligand ID: 9428

Synonyms: Elunate® | Fruzaqla® | HMPL-013 | HMPL013
Approved drug
fruquintinib is an approved drug (China (2018), FDA (2023))
Compound class: Synthetic organic
Comment: Fruquintinib (HMPL-013) is a potent and selective inhibitor of VEGFR 1-3 tyrosine kinases, that was developed for antineoplastic activity [1] (preclinical data is reported in this reference).
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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 CDK toolkit. 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 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 95.71
Molecular weight 393.13
XLogP 2.46
No. Lipinski's rules broken 0
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.

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Canonical SMILES CNC(=O)c1c(C)oc2c1ccc(c2)Oc1ncnc2c1cc(OC)c(c2)OC
Isomeric SMILES CNC(=O)c1c(C)oc2c1ccc(c2)Oc1ncnc2c1cc(OC)c(c2)OC
InChI InChI=1S/C21H19N3O5/c1-11-19(20(25)22-2)13-6-5-12(7-16(13)28-11)29-21-14-8-17(26-3)18(27-4)9-15(14)23-10-24-21/h5-10H,1-4H3,(H,22,25)
InChI Key BALLNEJQLSTPIO-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
HMPL-013 (as fruquintinib) is in Phase 3 clinical trial as monotherapy in patients with advanced non-small cell lung cancer (NSCLC; see NCT02691299) and Phase 2 for the same indication but in combination with the approved EGFR inhibitor gefitinib (see NCT02976116). In 2018 China's drug regulatory agency (NMPA) approved the use of fruquintinib to treat metastatic colorectal cancer that has been prevoiusly treated with at least 2 prior chemotherapy regimens, including those treated with anti-VEGF or anti-EGFR (WT) drugs. In November 2023 the FDA approved fruquintinib to treat highly pre-treated metastatic colorectal cancer.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02691299 A Phase III Clinical Trial of Fruquintinib in Patients With Advanced Non-small Cell Lung Cancer Phase 3 Interventional Hutchison Medipharma Limited
NCT02976116 A Phase II Study of Fruquintinib in Combination With Gefitinib in Patients With Advanced Non-small Cell Lung Cancer Phase 2 Interventional Hutchison Medipharma Limited
NCT02314819 A Phase III Trial Evaluating Fruquintinib Efficacy and Safety in 3+ Line Colorectal Cancer Patients （FRESCO) Phase 3 Interventional Hutchison Medipharma Limited
NCT04322539 A Study of Efficacy and Safety of Fruquintinib (HMPL-013) in Patients With Metastatic Colorectal Cancer Phase 3 Interventional Hutchison Medipharma Limited Results from this study will inform the progress of fruquintinib's development outside of China.