GtoPdb Ligand ID: 9601

Synonyms: AL-3818 | AL3818 | anlotinib
catequentinib is an approved drug (China (2018))
Compound class: Synthetic organic
Comment: Catequentinib (AL3818; anlotinib) 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..
2D Structure
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Physico-chemical Properties
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
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
Bioactivity Comments
In vitro and in vivo anti-tumour activities of AL3818 (dihydrochloride) are reported in WO2016179123 [2]. Data were obtained from patent WO2008112407 [1] which claims this and many structurally related compounds.
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
fms related receptor tyrosine kinase 4 Hs Inhibitor Inhibition 9.0 pIC50 - 1
pIC50 9.0 (IC50 1x10-9 M) [1]
Description: In vitro activity
fms related receptor tyrosine kinase 1 Hs Inhibitor Inhibition 8.4 pIC50 - 1
pIC50 8.4 (IC50 4x10-9 M) [1]
Description: In vitro activity
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 7.7 pIC50 - 1
pIC50 7.7 (IC50 2x10-8 M) [1]
Description: in vitro activity
kinase insert domain receptor Hs Inhibitor Inhibition 7.3 pIC50 - 1
pIC50 7.3 (IC50 4.5x10-8 M) [1]
Description: In vitro activity