Compound Detail

CHEMBL377300

BRIVANIB

🧪 Phase III

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🧪 Phase III

Cc1cc2c(F)c(Oc3ncnn4cc(OC[C@@H](C)O)c(C)c34)ccc2[nH]1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL377300
Name	BRIVANIB
Phase	Phase III
Structure Type	MOL
InChI Key	WCWUXEGQKLTGDX-LLVKDONJSA-N

Known Names

BMS-540215 Brivanib

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

370.4

MW (Da)

3.52

ALogP

HBA

HBD

84.7

PSA (Å²)

0.56

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

USAN Stem	-anib
USAN Year	2008

Extended Properties

Molecular Formula	C19H19FN4O3
MW	370.38
Aromatic Rings	4
Heavy Atoms	27
NP-Likeness	-0.84

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Fibroblast growth factor receptor inhibitor	INHIBITOR	Fibroblast growth factor receptor	✓	✓
Vascular endothelial growth factor receptor inhibitor	INHIBITOR	Vascular endothelial growth factor receptor	✓	✓

Indications

Carcinoma Carcinoma, Hepatocellular Liver Neoplasms Colorectal Neoplasms Colorectal Neoplasms Uterine Cervical Neoplasms Neoplasm Metastasis Neoplasms Neoplasms Ovarian Neoplasms

Activity Summary

Kd 66 meas. best 8.3

IC50 19 meas. best 7.6

Ki 3 meas. best 7.58

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Vascular endothelial growth factor receptor 2 CHEMBL279	Kd	8.3	8.3	5.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	Kd	8.0	8.0	10.0	1
Platelet-derived growth factor receptor alpha CHEMBL2007	Kd	7.96	7.96	11.0	1
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	7.92	7.21	12.0	6
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	7.6	7.59	25.0	4
Serine/threonine-protein kinase 35 CHEMBL5651	Kd	7.58	7.58	26.0	1
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	7.58	7.58	26.0	1
Fibroblast growth factor receptor 1 CHEMBL3650	IC50	7.55	7.31	28.0	3
Vascular endothelial growth factor receptor 2 CHEMBL3337	Ki	7.55	7.55	28.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	7.3	6.45	50.0	2
Vascular endothelial growth factor receptor 3 CHEMBL1955	Kd	7.25	7.25	56.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	Ki	7.22	7.22	60.0	1
Vascular endothelial growth factor receptor 2 CHEMBL3337	IC50	7.05	7.05	89.0	1
Fibroblast growth factor receptor 1 CHEMBL3650	Kd	7.0	7.0	99.0	1
Fibroblast growth factor receptor 2 CHEMBL4142	Kd	6.96	6.96	110.0	1
Fibroblast growth factor receptor 3 CHEMBL2742	Kd	6.82	6.81	150.0	2
TRAF2 and NCK-interacting protein kinase CHEMBL4527	Kd	6.8	6.8	160.0	1
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	Kd	6.8	6.395	160.0	2
STE20-like serine/threonine-protein kinase CHEMBL4202	Kd	6.77	6.165	170.0	2
Ephrin type-A receptor 6 CHEMBL4526	Kd	6.72	6.72	190.0	1
Serine/threonine-protein kinase 10 CHEMBL3981	Kd	6.66	5.825	220.0	2
Misshapen-like kinase 1 CHEMBL5518	Kd	6.51	6.51	310.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	6.44	6.13	360.0	3
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	6.42	6.42	380.0	1
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	6.41	6.0146	390.0	13
Angiopoietin-1 receptor CHEMBL4128	Kd	6.36	6.36	440.0	1
Mitogen-activated protein kinase kinase kinase 19 CHEMBL6191	Kd	6.3	6.3	500.0	1
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Kd	6.23	5.435	590.0	2
Fibroblast growth factor receptor 4 CHEMBL3973	Kd	6.22	6.22	600.0	1
HUVEC CHEMBL613979	IC50	6.21	6.15	618.0	3
Tyrosine-protein kinase Lck CHEMBL258	Kd	5.96	5.96	1100.0	1
Tyrosine-protein kinase receptor Tie-1 CHEMBL5274	Kd	5.96	5.96	1100.0	1
STE20-related kinase adapter protein alpha CHEMBL1795198	Kd	5.94	5.94	1137.0	1
Ephrin type-B receptor 6 CHEMBL5836	Kd	5.85	5.85	1400.0	1
Mitogen-activated protein kinase kinase kinase kinase 5 CHEMBL4852	Kd	5.85	5.85	1400.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	Kd	5.8	5.8	1600.0	1
Ephrin type-A receptor 7 CHEMBL4602	Kd	5.77	5.77	1700.0	1
Tyrosine-protein kinase ABL2 CHEMBL4014	Kd	5.75	5.75	1800.0	1
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	Kd	5.72	5.72	1900.0	1
Tyrosine-protein kinase Blk CHEMBL2250	Kd	5.7	5.7	2000.0	1
dengue virus type 2 CHEMBL613966	IC50	5.6	5.6	2500.0	1
Epidermal growth factor receptor CHEMBL203	Kd	5.58	5.4175	2600.0	4
Tyrosine-protein kinase HCK CHEMBL3234	Kd	5.57	5.57	2700.0	1
Receptor-interacting serine/threonine-protein kinase 2 CHEMBL5014	Kd	5.54	5.54	2900.0	1
Dual specificity mitogen-activated protein kinase kinase 5 CHEMBL4948	Kd	5.51	5.51	3100.0	1
Serine/threonine-protein kinase 33 CHEMBL6005	Kd	5.5	5.5	3200.0	1
Serine/threonine-protein kinase 32B CHEMBL5912	Kd	5.41	5.41	3900.0	1
ClpP1P2 CHEMBL4662931	IC50	5.16	4.89	6900.0	2
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	4.75	4.75	18000.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	4.75	4.6333	18000.0	3

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	50371.68	ng.hr.mL-1	Mus musculus
AUC	18148.62	ng.hr.mL-1	Mus musculus
AUC	82965.12	ng.hr.mL-1	Mus musculus
AUC	4963.09	ng.hr.mL-1	Rattus norvegicus
AUC	1240.77	ng.hr.mL-1	Rattus norvegicus
AUC	3122.3	ng.hr.mL-1	Rattus norvegicus
AUC	2818.59	ng.hr.mL-1	Rattus norvegicus
AUC	16667.1	ng.hr.mL-1	Mus musculus
AUC	19259.76	ng.hr.mL-1	Mus musculus
AUC	50371.68	ng.hr.mL-1	Mus musculus
AUC	30257.7	ugequiv/l.hr	Homo sapiens
AUC	7600.0	ng.hr.mL-1	Rattus norvegicus
AUC	6800.0	ng.hr.mL-1	Macaca fascicularis
AUC	21800.0	ng.hr.mL-1	Homo sapiens
AUC	35500.0	ng.hr.mL-1	Rattus norvegicus
AUC	45900.0	ng.hr.mL-1	Homo sapiens
AUC	49000.0	ng.hr.mL-1	Macaca fascicularis
AUC	23709.8	ugequiv/l.hr	Rattus norvegicus
AUC	42587.2	ugequiv/l.hr	Macaca fascicularis
CL	9.3	mL.min-1.kg-1	Mus musculus
CL	0.0031	mL.min-1.g-1	Homo sapiens
CL	0.016	uL/min	Homo sapiens
CL	0.031	uL/min	Homo sapiens
Cmax	41000.0	nM	Mus musculus
Cmax	6400.0	nM	Rattus norvegicus
Cmax	550.0	nM	Rattus norvegicus
Cmax	2050.0	nM	Rattus norvegicus
Cmax	1710.0	nM	Rattus norvegicus
Cmax	12000.0	nM	Mus musculus
Cmax	14000.0	nM	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Vascular endothelial growth factor receptor 2	Kd	=	5.0	nM	8.3	Binding constant for VEGFR2 kinase domain	22037378
Vascular endothelial growth factor receptor 1	Kd	=	10.0	nM	8.0	Binding constant for FLT1 kinase domain	22037378
Platelet-derived growth factor receptor alpha	Kd	=	11.0	nM	7.96	Binding constant for PDGFRA kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	12.0	nM	7.92	Binding constant for KIT(V559D,V654A) kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	17.0	nM	7.77	Binding constant for KIT(V559D,T670I) kinase domain	22037378
Vascular endothelial growth factor receptor 2	IC50	=	25.0	nM	7.6	Inhibitory activity against VEGFR2	16570908
Vascular endothelial growth factor receptor 2	IC50	=	25.0	nM	7.6	Inhibition of human VEGFR2	18395443
Vascular endothelial growth factor receptor 2	IC50	=	26.0	nM	7.58	Inhibition of recombinant VEGFR-2 (unknown origin)	22983304
Serine/threonine-protein kinase 35	Kd	=	26.0	nM	7.58	Binding constant for STK35 kinase domain	22037378
Vascular endothelial growth factor receptor 2	IC50	=	26.0	nM	7.58	Inhibition of human recombinant VEGFR-2	21289073
Vascular endothelial growth factor receptor 2	Ki	=	26.0	nM	7.58	Inhibitory activity against VEGFR2	16570908
Fibroblast growth factor receptor 1	IC50	=	28.0	nM	7.55	Inhibition of recombinant FGFR-1 (unknown origin)	22983304
Fibroblast growth factor receptor 1	IC50	=	28.0	nM	7.55	Inhibition of human recombinant FGFR-1	21289073
Vascular endothelial growth factor receptor 2	Ki	=	28.0	nM	7.55	Inhibitory activity against Flk1	16570908
Mast/stem cell growth factor receptor Kit	Kd	=	35.0	nM	7.46	Binding constant for KIT(V559D) kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	36.0	nM	7.44	Binding constant for KIT kinase domain	22037378
Platelet-derived growth factor receptor beta	Kd	=	50.0	nM	7.3	Binding constant for PDGFRB kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	54.0	nM	7.27	Binding constant for KIT(L576P) kinase domain	22037378
Vascular endothelial growth factor receptor 3	Kd	=	56.0	nM	7.25	Binding constant for FLT4 kinase domain	22037378
Vascular endothelial growth factor receptor 1	Ki	=	60.0	nM	7.22	Inhibitory activity against VEGFR1	16570908

Literature References

PubMed	DOI	Target Context	# Activities
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
21289073	10.1124/dmd.110.037341	Plasma	13
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
16570908	10.1021/jm051106d	Mus musculus	11
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
21289073	10.1124/dmd.110.037341	ADMET	8
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
16570908	10.1021/jm051106d	Rattus norvegicus	8
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
21989950	10.1124/dmd.111.042457	Cytochrome P450 1A2	6
21989950	10.1124/dmd.111.042457	Cytochrome P450 3A4	6
21289073	10.1124/dmd.110.037341	Rattus norvegicus	5
21289073	10.1124/dmd.110.037341	Cynomolgus monkey	5
21289073	10.1124/dmd.110.037341	Homo sapiens	5
18288793	10.1021/jm7013309	Mus musculus	5
22037378	10.1038/nbt.1990	Proto-oncogene tyrosine-protein kinase receptor Ret	4
21989950	10.1124/dmd.111.042457	ADMET	4
22983304	10.1124/dmd.112.047340	Liver cytosol	4
21989950	10.1124/dmd.111.042457	Liver microsome	4
16570908	10.1021/jm051106d	Vascular endothelial growth factor receptor 2	4

Data from ChEMBL 36 via Core Engine