catequentinib   Click here for help

GtoPdb Ligand ID: 9601

Synonyms: AL-3818 | AL3818 | anlotinib
Approved drug
catequentinib is an approved drug (China (2018))
Compound class: Synthetic organic
Comment: Catequentinib (AL3818; anlotinib in China) is a non-selective inhibitor of multiple receptor tyrosine kinases, including vascular endothelial growth factor receptor type 2 (VEGFR-2, FLT1) and type 3 (VEGFR-3, FLT4). It is being investigated for antineoplastic and anti-angiogenic potential. The dihydrochloride has PubChem CID 57380530. Preparation and crystallisation of AL3818 is described in patent WO2016179123 [2].
Note that anlotinib appears to be a 'pseudo' INN, that uses the -tinib INN stem for tyrosine kinase inhibitors, but has not been submitted to the World Health Organisation for ratification, and in fact a genuine INN request for 'catequentinib' was submitted for this chemical structure to the WHO (in Proposed List 121) and this became the recommended INN in April 2020..
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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 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 82.39
Molecular weight 407.16
XLogP 3.48
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 COc1cc2c(ccnc2cc1OCC1(N)CC1)Oc1ccc2c(c1F)cc([nH]2)C
Isomeric SMILES COc1cc2c(ccnc2cc1OCC1(N)CC1)Oc1ccc2c(c1F)cc([nH]2)C
InChI InChI=1S/C23H22FN3O3/c1-13-9-15-16(27-13)3-4-19(22(15)24)30-18-5-8-26-17-11-21(20(28-2)10-14(17)18)29-12-23(25)6-7-23/h3-5,8-11,27H,6-7,12,25H2,1-2H3
InChI Key KSMZEXLVHXZPEF-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Catequentinib (AL3818) is a clinical candidate for a number of advanced solid tumour types. Click here to link to ClinicalTrials.gov's full list of AL3818 studies. In May 2018, the China National Medical Products Administration (NMPA) approved catequentinib/anlotinib, as a treatment for patients with advanced non-small cell lung cancer (NSCLC) who have progressed after treatment with two or more lines of prior systemic chemotherapy [3-4].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02072031 Phase II Study of Anlotinib Versus Sunitinib in Patients With Advanced Renal Cell Carcinoma（RCC） Phase 2 Interventional Chia Tai Tianqing Pharmaceutical Group Co., Ltd.
NCT02558348 Phase 1/2a Evaluation of AL3818 in Subjects With Recurrent or Metastatic Endometrial, Ovarian or Cervical Cancer (AL3818-US-001) Phase 1/Phase 2 Interventional Advenchen Laboratories, LLC
NCT02809534 A Study of Anlotinib in Patients With Hepatocellular Carcinoma Phase 2 Interventional Chia Tai Tianqing Pharmaceutical Group Co., Ltd.
NCT03016819 A Phase III Trial of Anlotinib in Metastatic or Advanced Alveolar Soft Part Sarcoma, Leiomyosarcoma and Synovial Sarcoma Phase 3 Interventional Advenchen Laboratories, LLC