catequentinib   

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
SMILES / InChI / InChIKey
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
References
1. Chen GP. (2008)
Spiro substituted compounds as angiogenesis inhibitors.
Patent number: WO2008112407 A1. Assignee: Advenchen Laboratories, Llc. Priority date: 14/03/2007. Publication date: 18/09/2008.
2. Chen GP, Yan C. (2016)
Process for preparing an anti-cancer agent, 1-((4-(4-fluoro-2-methyl-1h-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)methyl) cyclopropanamine, its crystalline form and its salts.
Patent number: WO2016179123. Assignee: Advenchen Pharmaceuticals, LLC. Priority date: 04/05/2015. Publication date: 10/11/2016.
3. Zhou M, Chen X, Zhang H, Xia L, Tong X, Zou L, Hao R, Pan J, Zhao X, Chen D et al.. (2019)
China National Medical Products Administration approval summary: anlotinib for the treatment of advanced non-small cell lung cancer after two lines of chemotherapy.
Cancer Commun (Lond), 39 (1): 36. [PMID:31221221]