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
No information available.
Summary of Clinical Use
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 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].
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