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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H24FN3O5.C4H6O5
Molecular Weight 635.5931
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABOZANTINIB S-MALATE

SMILES

O[C@@H](CC(O)=O)C(O)=O.COC1=CC2=NC=CC(OC3=CC=C(NC(=O)C4(CC4)C(=O)NC5=CC=C(F)C=C5)C=C3)=C2C=C1OC

InChI

InChIKey=HFCFMRYTXDINDK-WNQIDUERSA-N
InChI=1S/C28H24FN3O5.C4H6O5/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;5-2(4(8)9)1-3(6)7/h3-11,14-16H,12-13H2,1-2H3,(H,31,33)(H,32,34);2,5H,1H2,(H,6,7)(H,8,9)/t;2-/m.0/s1

HIDE SMILES / InChI

Description

Cabozantinib (development code name XL184; marketed under the trade name Cometriq) is an orally bioavailable, small molecule receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. Cabozantinib strongly binds to and inhibits several RTKs, which are often overexpressed in a variety of cancer cell types, including hepatocyte growth factor receptor (MET), RET (rearranged during transfection), vascular endothelial growth factor receptor types 1 (VEGFR-1), 2 (VEGFR-2), and 3 (VEGFR-3), mast/stem cell growth factor (KIT), FMS-like tyrosine kinase 3 (FLT-3), TIE-2 (TEK tyrosine kinase, endothelial), tropomyosin-related kinase B (TRKB) and AXL. This may result in an inhibition of both tumor growth and angiogenesis, and eventually lead to tumor regression. Cabozantinib was granted orphan drug status by the U.S. Food and Drug Administration (FDA) in January 2011. It is currently undergoing clinical trials for the treatment of prostate, bladder, ovarian, brain, melanoma, breast, non-small cell lung, pancreatic, hepatocellular and kidney cancers.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Cabozantinib (XL184), a novel MET and VEGFR2 inhibitor, simultaneously suppresses metastasis, angiogenesis, and tumor growth.
2011 Dec
Cabozantinib versus Everolimus in Advanced Renal-Cell Carcinoma.
2015 Nov 5
Patents

Sample Use Guides

In Vivo Use Guide
Recommended Dose: 140 mg orally, once daily
Route of Administration: Oral
In Vitro Use Guide
For in vitro assays, 10 mM cabozantinib stock solutions were prepared in dimethyl sulfoxide (DMSO) and diluted in the appropriate media.
Name Type Language
CABOZANTINIB S-MALATE
ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
N-(4-((6,7-DIMETHOXYQUINOLIN-4-YL)OXY)PHENYL)-N'-(4-FLUOROPHENYL)CYCLOPROPANE-1,1-DICARBOXAMIDE MONO((2S)-2-HYDROXYBUTANEDIOATE)
Systematic Name English
XL-184
Code English
XL184
Code English
BMS-907351
Code English
CABOZANTINIB S-MALATE [ORANGE BOOK]
Common Name English
CABOZANTINIB S-MALATE [USAN]
Common Name English
CABOMETYX
Brand Name English
CABOZANTINIB S-MALATE [WHO-DD]
Common Name English
BUTANEDIOIC ACID, 2-HYDROXY-, (2S)-, COMPD. WITH N-(4-((6,7-DIMETHOXY-4-QUINOLINYL)OXY)PHENYL)-N'-(4-FLUOROPHENYL)-1,1-CYCLOPROPANEDICARBOXAMIDE (1:1)
Common Name English
COMETRIQ
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
EU-Orphan Drug EU/3/08/610
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
NCI_THESAURUS C1742
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
NCI_THESAURUS C129825
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL2105717
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
PRIMARY
CAS
1140909-48-3
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
PRIMARY
EVMPD
SUB176318
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
PRIMARY
PUBCHEM
25102846
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
PRIMARY
NCI_THESAURUS
C97938
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
PRIMARY
RXCUI
1363267
Created by admin on Mon Oct 21 19:58:22 UTC 2019 , Edited by admin on Mon Oct 21 19:58:22 UTC 2019
PRIMARY RxNorm