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Compound Detail

CHEMBL1336

SORAFENIB
💊 Approved Drug
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💊 Approved Drug
CNC(=O)c1cc(Oc2ccc(NC(=O)Nc3ccc(Cl)c(C(F)(F)F)c3)cc2)ccn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1336
Name SORAFENIB
Phase Approved
Structure Type MOL
InChI Key MLDQJTXFUGDVEO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BAY 43-9006 BAY-43-9006 Sorafenib
522
Targets
2,059
Activities
4
Assay Types
14
PK Parameters
20
Publications
3
Known Names
20
Indications

Molecular Properties

464.8
MW (Da)
5.55
ALogP
4
HBA
3
HBD
92.3
PSA (Ų)
0.46
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Stem -rafenib
USAN Year 2007

Extended Properties

Molecular Formula C21H16ClF3N4O3
MW 464.83
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.46

Indications

Breast Neoplasms Carcinoma Carcinoma, Hepatocellular Carcinoma, Non-Small-Cell Lung Carcinoma, Renal Cell Hepatoblastoma Kidney Neoplasms Kidney Neoplasms Liver Neoplasms Liver Neoplasms Liver Neoplasms Liver Neoplasms Melanoma Neoplasms Neoplasms Thyroid Neoplasms Thyroid Neoplasms Thyroid Neoplasms Thyroid Neoplasms Adenocarcinoma

ATC Classification

L01EX02
sorafenib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 1,568 meas. best 10.22
Kd 416 meas. best 8.82
Ki 52 meas. best 10.68
EC50 23 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vascular endothelial growth factor receptor 2
CHEMBL279
 Ki 10.68 8.915 0.0 4
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 10.22 7.491 0.1 102
Ephrin type-B receptor 4
CHEMBL5147
 IC50 9.7 7.8338 0.2 8
Platelet-derived growth factor receptor beta
CHEMBL1913
 IC50 9.59 7.4246 0.3 13
Angiopoietin-1 receptor
CHEMBL4128
 IC50 9.41 8.2517 0.4 6
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 9.25 7.4775 0.6 4
HUVEC
CHEMBL613979
 IC50 9.23 5.3353 0.6 15
MV4-11
CHEMBL613835
 IC50 9.06 8.0158 0.9 12
PLC-PRF-5
CHEMBL1075561
 IC50 9.0 6.2133 1.0 3
SNU-387
CHEMBL1075583
 IC50 9.0 6.33 1.0 3
RAF proto-oncogene serine/threonine-protein kinase
CHEMBL1906
 IC50 9.0 7.46 1.0 38
K562
CHEMBL385
 IC50 9.0 5.6958 1.0 12
MCF7
CHEMBL387
 IC50 9.0 5.4425 1.0 36
PC-3
CHEMBL390
 IC50 9.0 5.4708 1.0 12
HepG2
CHEMBL395
 IC50 9.0 5.2456 1.0 68
SU-DHL-6
CHEMBL4296496
 IC50 9.0 7.21 1.0 2
Serine/threonine-protein kinase B-raf
CHEMBL5145
 IC50 9.0 7.3475 1.0 63
Huh-7
CHEMBL614039
 IC50 9.0 5.4086 1.0 14
MOLT-4
CHEMBL614177
 IC50 9.0 6.055 1.0 6
SNU-398
CHEMBL614454
 IC50 9.0 7.235 1.0 2
Raji
CHEMBL614628
 IC50 9.0 6.2167 1.0 3
Ramos
CHEMBL614629
 IC50 9.0 9.0 1.0 1
SK-HEP1
CHEMBL614912
 IC50 9.0 5.7043 1.0 7
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 8.89 7.6545 1.3 29
TT
CHEMBL2366083
 IC50 8.85 8.85 1.4 1
Epithelial discoidin domain-containing receptor 1
CHEMBL5319
 Kd 8.82 8.214 1.5 5
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.64 5.3907 2.3 67
Homeodomain-interacting protein kinase 4
CHEMBL1075167
 Kd 8.57 8.525 2.7 2
Epidermal growth factor receptor
CHEMBL203
 IC50 8.53 6.9369 3.0 13
Homeodomain-interacting protein kinase 4
CHEMBL1075167
 IC50 8.52 7.76 3.0 2
Vascular endothelial growth factor receptor 3
CHEMBL1955
 IC50 8.52 7.3675 3.0 8
Serine/threonine-protein kinase B-raf
CHEMBL5145
 EC50 8.52 8.52 3.0 1
Platelet-derived growth factor receptor beta
CHEMBL1913
 Ki 8.4 8.4 4.0 1
MONO-MAC-6
CHEMBL2366062
 IC50 8.38 8.38 4.2 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 Kd 8.35 7.4866 4.5 29
Fibroblast growth factor receptor 1
CHEMBL3650
 IC50 8.33 6.63 4.6 5
MOLM-13
CHEMBL3706572
 IC50 8.3 8.18 5.0 2
Proto-oncogene tyrosine-protein kinase receptor Ret
CHEMBL2041
 IC50 8.23 7.7096 5.9 24
RAF proto-oncogene serine/threonine-protein kinase
CHEMBL1906
 Ki 8.22 8.22 6.0 2
BaF3
CHEMBL614524
 IC50 8.22 6.255 6.0 16
Mitogen-activated protein kinase kinase kinase 20
CHEMBL3886
 Kd 8.2 7.685 6.3 4
Discoidin domain-containing receptor 2
CHEMBL5122
 Kd 8.18 7.5829 6.6 7
Serine/threonine-protein kinase A-Raf
CHEMBL1169596
 IC50 8.15 8.0733 7.1 3
Discoidin domain-containing receptor 2
CHEMBL5122
 IC50 8.15 7.795 7.0 2
Proto-oncogene tyrosine-protein kinase receptor Ret
CHEMBL2041
 Kd 8.13 7.695 7.4 12
Unchecked
CHEMBL612545
 IC50 8.1 5.7389 7.9 47
Homeodomain-interacting protein kinase 4
CHEMBL1075167
 Ki 8.0 8.0 10.0 1
Mast/stem cell growth factor receptor Kit
CHEMBL1936
 IC50 8.0 7.135 10.0 8
Mast/stem cell growth factor receptor Kit
CHEMBL1936
 Kd 7.96 7.153 11.0 23
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 7.92 7.92 12.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 111559.2 ng.hr.mL-1 Mus musculus
CL 4.38 uL/min/pmol Homo sapiens
Cmax 12000.0 nM Mus musculus
Cmax 132.0 nM Homo sapiens
T1/2 0.02667 hr Homo sapiens
T1/2 30.0 hr Homo sapiens
T1/2 4.833 hr Homo sapiens
T1/2 0.1333 hr Homo sapiens
T1/2 0.3 hr Homo sapiens
T1/2 5.6 hr Homo sapiens
T1/2 5.6 hr Homo sapiens
T1/2 6.8 hr Rattus norvegicus
T1/2 21.89 hr Rattus norvegicus
Tmax 3.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vascular endothelial growth factor receptor 2 Ki = 0.021 nM 10.68 Inhibition of human N-terminal His-tagged non-phosphorylated VEGFR2 after 60 min... 21885287
Vascular endothelial growth factor receptor 2 IC50 = 0.06 nM 10.22 Inhibition of VEGFR2 (unknown origin) using ULight-4E-BP1 peptide as substrate i... 33129590
Vascular endothelial growth factor receptor 2 Ki = 0.12 nM 9.92 Inhibition of human N-terminal His-tagged non-phosphorylated VEGFR2 after 60 min... 21885287
Vascular endothelial growth factor receptor 2 IC50 = 0.16 nM 9.8 Inhibition of human N-terminal His-tagged non-phosphorylated VEGFR2 preincubated... 21885287
Ephrin type-B receptor 4 IC50 = 0.2 nM 9.7 Inhibition of EphB4 (unknown origin) after 60 mins by ADP-Glo assay 28068599
Ephrin type-B receptor 4 IC50 = 0.22 nM 9.66 Inhibition of EphB4 (unknown origin) after 1 hrs by ADP-Glo luminescence assay 30616052
Ephrin type-B receptor 4 IC50 = 0.22 nM 9.66 Inhibition of EPHB4 (unknown origin) after 4 hrs by ADP-Glo reagent based lumine... 30503935
Platelet-derived growth factor receptor beta IC50 = 0.26 nM 9.59 In vitro kinase inhibition assay: An in vitro kinase assay was performed to eval... -
Vascular endothelial growth factor receptor 2 IC50 = 0.34 nM 9.47 In vitro kinase inhibition assay: An in vitro kinase assay was performed to eval... -
Angiopoietin-1 receptor IC50 = 0.39 nM 9.41 Inhibition of Tie-2 (unknown origin) after 1 hrs by ADP-Glo luminescence assay 30616052
Angiopoietin-1 receptor IC50 = 0.39 nM 9.41 Inhibition of TIE2 (unknown origin) after 4 hrs by ADP-Glo reagent based lumines... 30503935
Vascular endothelial growth factor receptor 2 IC50 = 0.45 nM 9.35 Inhibition of VEGFR2 (unknown origin) after 60 mins by ADP-Glo assay 28068599
Vascular endothelial growth factor receptor 2 IC50 = 0.48 nM 9.32 Inhibition of VEGFR-2 (unknown origin) after 1 hr by ADP-Glo assay 26342134
Vascular endothelial growth factor receptor 2 IC50 = 0.48 nM 9.32 Inhibition of VEGFR-2 (unknown origin) after 1 hr by ADP-Glo assay 25982075
Vascular endothelial growth factor receptor 2 IC50 = 0.55 nM 9.26 Inhibition of human VEGFR-2 37453330
Receptor tyrosine-protein kinase erbB-2 IC50 = 0.56 nM 9.25 In vitro kinase inhibition assay: An in vitro kinase assay was performed to eval... -
HUVEC IC50 = 0.59 nM 9.23 Antiangiogenic activity against HUVEC after 24 hrs by calcein AM staining-based ... 18849971
Angiopoietin-1 receptor IC50 = 0.83 nM 9.08 Inhibition of TIE-2 (unknown origin) after 60 mins by ADP-Glo assay 28068599
Vascular endothelial growth factor receptor 2 IC50 = 0.85 nM 9.07 Inhibition of VEGFR2 (unknown origin) using ATP measured luminescence by ADP-Glo... 25637123
Vascular endothelial growth factor receptor 2 IC50 = 0.85 nM 9.07 Inhibition of VEGFR-2 (unknown origin) after 60 mins by ADP-Glo luminescence ass... 29102175

Literature References

PubMed DOI Target Context # Activities
18077425 10.1073/pnas.0707498104 NON-PROTEIN TARGET 232
27017549 10.1016/j.ejmech.2016.02.039 NON-PROTEIN TARGET 103
28342400 10.1016/j.ejmech.2017.03.034 Hep 3B2 70
26590508 10.1016/j.ejmech.2015.10.053 NON-PROTEIN TARGET 34
27208658 10.1016/j.ejmech.2016.03.015 NON-PROTEIN TARGET 20
18783202 10.1021/jm800539g Unchecked 18
26254279 10.18632/oncotarget.4214 Unchecked 18
26560049 10.1016/j.ejmech.2015.10.045 A549 17
22037378 10.1038/nbt.1990 Tyrosine-protein kinase ABL1 15
18077425 10.1073/pnas.0707498104 HeLa 14
36395650 10.1016/j.ejmech.2022.114912 UO-31 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18077425 10.1073/pnas.0707498104 COLO 14
21885287 10.1016/j.bmc.2011.08.002 Vascular endothelial growth factor receptor 2 13
35639640 10.1021/acs.jmedchem.2c00520 Huh-7 13
26629594 10.1021/acs.jmedchem.5b01582 BaF3 12
30826508 10.1016/j.ejmech.2019.02.050 A549 12
32827851 10.1016/j.ejmech.2020.112661 T-24 12
33761256 10.1021/acs.jmedchem.0c02253 Unchecked 12
22037378 10.1038/nbt.1990 Epidermal growth factor receptor 12

Data from ChEMBL 36 via Core Engine