Compound Detail

CHEMBL276711

SEMAXANIB

🧪 Phase III

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🧪 Phase III

Cc1cc(C)c(/C=C2\C(=O)Nc3ccccc32)[nH]1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL276711
Name	SEMAXANIB
Phase	Phase III
Structure Type	MOL
InChI Key	WUWDLXZGHZSWQZ-WQLSENKSSA-N

Known Names

NSC-696819 Semaxanib Semaxinib Su-5416 SU005416 SU5416

Targets

105

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

238.3

MW (Da)

3.12

ALogP

HBA

HBD

44.9

PSA (Å²)

0.74

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem	-anib
USAN Year	2000

Extended Properties

Molecular Formula	C15H14N2O
MW	238.29
Aromatic Rings	2
Heavy Atoms	18
NP-Likeness	-0.24

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Stem cell growth factor receptor inhibitor	INHIBITOR	Mast/stem cell growth factor receptor Kit	✓	✓
Vascular endothelial growth factor receptor inhibitor	INHIBITOR	Vascular endothelial growth factor receptor	✓	✓

Indications

Colorectal Neoplasms Colorectal Neoplasms Carcinoma, Renal Cell Kidney Neoplasms Melanoma Melanoma Mesothelioma Multiple Myeloma Neoplasms, Plasma Cell Prostatic Neoplasms, Castration-Resistant Sarcoma Uterine Cervical Neoplasms Breast Neoplasms Central Nervous System Neoplasms Colonic Neoplasms Head and Neck Neoplasms Neoplasms Rectal Neoplasms

Activity Summary

IC50 103 meas. best 8.51

EC50 2 meas. best 4.94

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MCF7 CHEMBL387	IC50	8.51	7.115	3.1	2
B16-F10 CHEMBL612656	IC50	8.44	8.44	3.6	1
PBMC CHEMBL613107	IC50	8.3	8.3	5.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	8.1	7.09	8.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.52	5.9514	30.0	7
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	7.46	6.68	35.0	3
HUVEC CHEMBL613979	IC50	7.4	5.68	40.0	3
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	7.4	5.6384	40.0	31
Vascular endothelial growth factor receptor 3 CHEMBL1955	IC50	7.3	6.8	50.0	2
Chorioallantoic membrane CHEMBL2367390	IC50	7.22	6.17	60.0	3
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	7.17	5.6042	68.0	12
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	IC50	7.08	7.08	84.0	1
A-431 CHEMBL614069	IC50	7.07	5.3075	85.0	4
Gallus gallus CHEMBL613109	IC50	7.07	7.07	85.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	6.8	6.8	160.0	2
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	IC50	6.77	6.77	170.0	1
Platelet-derived growth factor receptor alpha CHEMBL2007	IC50	6.7	6.7	200.0	1
Vascular endothelial growth factor receptor 2 CHEMBL3337	IC50	5.98	5.98	1040.0	1
Vascular endothelial growth factor receptor 1 CHEMBL3516	IC50	5.98	5.98	1040.0	1
Unchecked CHEMBL612545	IC50	5.98	5.98	1040.0	1
ALK tyrosine kinase receptor CHEMBL4247	IC50	5.92	5.83	1200.0	2
Platelet-derived growth factor receptor CHEMBL2096980	IC50	5.39	4.9233	4050.0	3
Fibroblast growth factor receptor 1 CHEMBL3650	IC50	5.38	4.995	4200.0	4
Fibroblast growth factor receptor CHEMBL2095217	IC50	5.3	5.3	5000.0	1
Plasmodium falciparum CHEMBL364	IC50	5.1	5.1	7943.3	1
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	4.96	4.96	11000.0	1
Oxytocin receptor CHEMBL2049	EC50	4.94	4.94	11468.0	1
Vasopressin V1a receptor CHEMBL1889	EC50	4.92	4.92	12070.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	4.79	4.79	16400.0	1
HeLa CHEMBL399	IC50	4.7	4.7	20000.0	1
Tyrosine-protein kinase ZAP-70 CHEMBL2803	IC50	4.68	4.68	20700.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	45.0	mL.min-1.kg-1	Rattus norvegicus
CL	52.0	mL.min-1.kg-1	Canis lupus familiaris
CL	14.0	mL.min-1.kg-1	Homo sapiens
CL	25.7	mL.min-1.kg-1	Macaca
Cmax	300000.0	nM	Mus musculus
Tmax	0.5	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MCF7	IC50	=	3.1	nM	8.51	Cytotoxicity against human MCF7 cells after 48 hrs by CCK8 assay	23777898
B16-F10	IC50	=	3.6	nM	8.44	Cytotoxicity against mouse B16F10 cells after 48 hrs by CCK8 assay	23777898
PBMC	IC50	=	5.0	nM	8.3	In vitro inhibitory concentration on the production of pro-inflammatory cytokine...	16107139
Vascular endothelial growth factor receptor 1	IC50	=	8.0	nM	8.1	Inhibition of VEGF-receptor 1, Flt-1	10882357
NON-PROTEIN TARGET	IC50	=	30.0	nM	7.52	Antiangiogenic activity in chicken embryo chorioallantoic membrane assessed as i...	19748785
Mast/stem cell growth factor receptor Kit	IC50	=	35.0	nM	7.46	In vitro inhibition of Mast/stem cell growth factor receptor (c-Kit kinase) expr...	12477352
HUVEC	IC50	=	40.0	nM	7.4	Evaluated for the inhibition of cell proliferation induced by VEGF in HUVEC or N...	10893303
Vascular endothelial growth factor receptor 2	IC50	=	40.0	nM	7.4	Inhibitory activity of compound against VEGF induced cell proliferation	10602697
NON-PROTEIN TARGET	IC50	=	40.0	nM	7.4	Antiangiogenic activity in fertilized chicken egg by CAM assay	20558072
NON-PROTEIN TARGET	IC50	=	40.0	nM	7.4	Antiangiogenic activity in VEGF/bFGF-stimulated chicken embryo after 48 hrs by C...	22739090
Vascular endothelial growth factor receptor 1	IC50	=	43.0	nM	7.37	In vitro inhibition of Vascular endothelial growth factor receptor 1 (VEGFR-1) e...	12477352
Vascular endothelial growth factor receptor 1	IC50	=	43.0	nM	7.37	Inhibition of VEGFR1 (unknown origin)	-
Vascular endothelial growth factor receptor 3	IC50	=	50.0	nM	7.3	In vitro inhibition of Vascular endothelial growth factor receptor 3 [VEGFR-3(Fl...	12477352
Chorioallantoic membrane	IC50	=	60.0	nM	7.22	Antiangiogenic activity in fertile leghorn chicken egg Chorioallantoic membrane ...	24890652
Platelet-derived growth factor receptor beta	IC50	=	68.0	nM	7.17	Inhibition of PDGFRbeta	16565716
Platelet-derived growth factor receptor beta	IC50	=	68.0	nM	7.17	Inhibition of PDGFRb (unknown origin)	-
Macrophage colony-stimulating factor 1 receptor	IC50	=	84.0	nM	7.08	In vitro inhibition of Colony stimulating factor 1 receptor (CSF-1R) expressed i...	12477352
Gallus gallus	IC50	=	85.0	nM	7.07	Antiangiogenic activity against fertile leghorn chicken eggs by CAM assay	18467105
Chorioallantoic membrane	IC50	=	85.0	nM	7.07	Inhibition of VEGF165/bFGF-induced angiogenesis in chicken chorioallantoic membr...	23375090
A-431	IC50	=	85.0	nM	7.07	Antiangiogenic activity against human A431 cells	20403693

Literature References

PubMed	DOI	Target Context	# Activities
16621936	10.1124/dmd.105.006619	ADMET	8
30098912	10.1016/j.bmc.2018.07.037	Danio rerio	5
23398362	10.1042/bj20121418	Insulin receptor	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
23398362	10.1042/bj20121418	cGMP-dependent protein kinase 1	4
23398362	10.1042/bj20121418	Serine/threonine-protein kinase mTOR	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase Lck	4
26318056	10.1016/j.ejmech.2015.08.027	Aorta	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase HCK	4
23398362	10.1042/bj20121418	Protein kinase C beta type	4
23398362	10.1042/bj20121418	Cyclin-dependent kinase 5/CDK5 activator 1	4
10893303	10.1021/jm9906116	HUVEC	4
23398362	10.1042/bj20121418	Insulin-like growth factor 1 receptor	4
10602697	10.1021/jm9904295	Vascular endothelial growth factor receptor 2	3
23124213	10.1016/j.ejmech.2012.10.001	NON-PROTEIN TARGET	3
-	10.6019/CHEMBL4808148	Histone deacetylase 6	3
12477352	10.1021/jm020899q	Vascular endothelial growth factor receptor 2	3
27894589	10.1016/j.bmc.2016.11.026	Unchecked	3
12477352	10.1021/jm020899q	Fibroblast growth factor receptor 1	3
20014752	10.1021/tx900326k	Hepatotoxicity	3

Data from ChEMBL 36 via Core Engine