cabozantinib   

GtoPdb Ligand ID: 5887

Synonyms: BMS907351 | Cabometyx® | Cometriq® | XL-184 | XL184
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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2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
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]