ifebemtinib   Click here for help

GtoPdb Ligand ID: 12369

Synonyms: BI-853520 | BI853520 | IN10018
Compound class: Synthetic organic
Comment: We mapped the structure for the INN ifebemtinib via PubChem to the research code BI-853520. BI-853520 is a selective, ATP-competitive inhibitor of focal adhesion kinase (FAK), that has anti-tumour effects in preclinical [3,5] and early clinical studies [1-2]. FAK inhibitors enhance effector T cell infiltration into the tumour microenvironment [4].
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 8
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 108.92
Molecular weight 588.21
XLogP 3.92
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 COc1cc(C(=O)NC2CCN(CC2)C)c(cc1Nc1ncc(c(n1)Oc1cccc2c1C(=O)N(C2)C)C(F)(F)F)F
Isomeric SMILES CN1CCC(CC1)NC(=O)c1cc(c(cc1F)Nc1ncc(c(n1)Oc1cccc2c1C(=O)N(C2)C)C(F)(F)F)OC
InChI InChI=1S/C28H28F4N6O4/c1-37-9-7-16(8-10-37)34-24(39)17-11-22(41-3)20(12-19(17)29)35-27-33-13-18(28(30,31)32)25(36-27)42-21-6-4-5-15-14-38(2)26(40)23(15)21/h4-6,11-13,16H,7-10,14H2,1-3H3,(H,34,39)(H,33,35,36)
InChI Key ULMMVBPTWVRPSI-UHFFFAOYSA-N
References
1. de Jonge MJA, Steeghs N, Lolkema MP, Hotte SJ, Hirte HW, van der Biessen DAJ, Abdul Razak AR, De Vos FYFL, Verheijen RB, Schnell D et al.. (2019)
Phase I Study of BI 853520, an Inhibitor of Focal Adhesion Kinase, in Patients with Advanced or Metastatic Nonhematologic Malignancies.
Target Oncol, 14 (1): 43-55. [PMID:30756308]
2. Doi T, Yang JC, Shitara K, Naito Y, Cheng AL, Sarashina A, Pronk LC, Takeuchi Y, Lin CC. (2019)
Phase I Study of the Focal Adhesion Kinase Inhibitor BI 853520 in Japanese and Taiwanese Patients with Advanced or Metastatic Solid Tumors.
Target Oncol, 14 (1): 57-65. [PMID:30725402]
3. Hirt UA, Waizenegger IC, Schweifer N, Haslinger C, Gerlach D, Braunger J, Weyer-Czernilofsky U, Stadtmüller H, Sapountzis I, Bader G et al.. (2018)
Efficacy of the highly selective focal adhesion kinase inhibitor BI 853520 in adenocarcinoma xenograft models is linked to a mesenchymal tumor phenotype.
Oncogenesis, 7 (2): 21. [PMID:29472531]
4. Osipov A, Blair AB, Liberto J, Wang J, Li K, Herbst B, Xu Y, Li S, Niu N, Rashid R et al.. (2021)
Inhibition of focal adhesion kinase enhances antitumor response of radiation therapy in pancreatic cancer through CD8+ T cells.
Cancer Biol Med, 18 (1): 206-214. [PMID:33628595]
5. Tiede S, Meyer-Schaller N, Kalathur RKR, Ivanek R, Fagiani E, Schmassmann P, Stillhard P, Häfliger S, Kraut N, Schweifer N et al.. (2018)
The FAK inhibitor BI 853520 exerts anti-tumor effects in breast cancer.
Oncogenesis, 7 (9): 73. [PMID:30237500]