cabozantinib   Click here for help

GtoPdb Ligand ID: 5887

Synonyms: BMS907351 | Cabometyx® | Cometriq® | XL-184 | XL184
Approved drug
cabozantinib is an approved drug (FDA (2012), EMA (2014))
Compound class: Synthetic organic
Comment: Cabozantinib is a Type-1, oral, small-molecule tyrosine kinase inhibitor.
Marketed formulations contain cabozantinib S-malate (PubChem CID 25102846).
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: cabozantinib

cabozantinib is commercially available from our sponsors

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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 5
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 98.78
Molecular weight 501.17
XLogP 4.58
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1cc2c(ccnc2cc1OC)Oc1ccc(cc1)NC(=O)C1(CC1)C(=O)Nc1ccc(cc1)F
Isomeric SMILES COc1cc2c(ccnc2cc1OC)Oc1ccc(cc1)NC(=O)C1(CC1)C(=O)Nc1ccc(cc1)F
InChI InChI=1S/C28H24FN3O5/c1-35-24-15-21-22(16-25(24)36-2)30-14-11-23(21)37-20-9-7-19(8-10-20)32-27(34)28(12-13-28)26(33)31-18-5-3-17(29)4-6-18/h3-11,14-16H,12-13H2,1-2H3,(H,31,33)(H,32,34)
InChI Key ONIQOQHATWINJY-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Abou-Alfa GK, Meyer T, Cheng AL, El-Khoueiry AB, Rimassa L, Ryoo BY, Cicin I, Merle P, Chen Y, Park JW et al.. (2018)
Cabozantinib in Patients with Advanced and Progressing Hepatocellular Carcinoma.
N Engl J Med, 379 (1): 54-63. [PMID:29972759]
2. Choueiri TK, Escudier B, Powles T, Mainwaring PN, Rini BI, Donskov F, Hammers H, Hutson TE, Lee JL, Peltola K et al.. (2015)
Cabozantinib versus Everolimus in Advanced Renal-Cell Carcinoma.
N Engl J Med, 373 (19): 1814-23. [PMID:26406150]
3. FDA. 
FDA approves cabozantinib for hepatocellular carcinoma.
Accessed on 16/01/2019. Modified on 16/01/2019. www.fda.gov, https://www.fda.gov/Drugs/InformationOnDrugs/ApprovedDrugs/ucm629512.htm?utm_campaign=Oncology%201%2F15%2F2019%20cabozantinib&utm_medium=email&utm_source=Eloqua&elqTrackId=f0cd47cbe0e04a7e88308645f7d66a61&elq=249a34ffaff94fdb97f2d843ed80fa79&elqaid=6487&elqat=1&elqCampaignId=5289
4. FDA. 
FDA grants regular approval to Cabometyx for first-line treatment of advanced renal cell carcinoma.
Accessed on 03/01/2018. Modified on 03/01/2018. fda.gov, https://www.fda.gov/Drugs/InformationOnDrugs/ApprovedDrugs/ucm589842.htm?utm_campaign=Oncology%2012%2F20&utm_medium=email&utm_source=Eloqua&elqTrackId=9bc32150b77e4929b686ed8a82ffbb6e&elq=70477587f45543ad83873a1367bab364&elqaid=1850&elqat=1&elqCampaignId=1227
5. Subbiah V, Gainor JF, Rahal R, Brubaker JD, Kim JL, Maynard M, Hu W, Cao Q, Sheets MP, Wilson D et al.. (2018)
Precision Targeted Therapy with BLU-667 for RET-Driven Cancers.
Cancer Discov, 8 (7): 836-849. [PMID:29657135]
6. Yakes FM, Chen J, Tan J, Yamaguchi K, Shi Y, Yu P, Qian F, Chu F, Bentzien F, Cancilla B et al.. (2011)
Cabozantinib (XL184), a novel MET and VEGFR2 inhibitor, simultaneously suppresses metastasis, angiogenesis, and tumor growth.
Mol Cancer Ther, 10 (12): 2298-308. [PMID:21926191]