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Compound Detail

CHEMBL1200485

SORAFENIB TOSYLATE
💊 Approved Drug
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💊 Approved Drug
CNC(=O)c1cc(Oc2ccc(NC(=O)Nc3ccc(Cl)c(C(F)(F)F)c3)cc2)ccn1.Cc1ccc(S(=O)(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200485
Name SORAFENIB TOSYLATE
Phase Approved
Structure Type MOL
InChI Key IVDHYUQIDRJSTI-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL1336
Active Moiety CHEMBL1336

Known Names

BAY 54-9085 BAY-54-9085 Nexavar Sorafenib accord Sorafenib tosilate Sorafenib tosylate
14
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
20
Indications
7
Mechanisms

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 C28H24ClF3N4O6S
MW 637.04
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.46

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serine/threonine-protein kinase RAF inhibitor INHIBITOR RAF proto-oncogene serine/threonine-protein kinase ✓ ✓
Platelet-derived growth factor receptor beta inhibitor INHIBITOR Platelet-derived growth factor receptor beta ✓ ✓
Stem cell growth factor receptor inhibitor INHIBITOR Mast/stem cell growth factor receptor Kit ✓ ✓
Tyrosine-protein kinase receptor FLT3 inhibitor INHIBITOR Receptor-type tyrosine-protein kinase FLT3 ✓ ✓
Serine/threonine-protein kinase B-raf inhibitor INHIBITOR Serine/threonine-protein kinase B-raf ✓ ✓
Vascular endothelial growth factor receptor inhibitor INHIBITOR Vascular endothelial growth factor receptor ✓ ✓
Tyrosine-protein kinase receptor RET inhibitor INHIBITOR Proto-oncogene tyrosine-protein kinase receptor Ret ✓ ✓

Indications

Carcinoma, Hepatocellular Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Thyroid Neoplasms Thyroid Neoplasms Thyroid Neoplasms Desmoid Tumors Kidney Neoplasms Leukemia Leukemia, Myeloid, Acute Liver Neoplasms Liver Neoplasms Liver Neoplasms Melanoma Melanoma Pancreatic Neoplasms Sarcoma, Myeloid Adenocarcinoma, Follicular

Activity Summary

IC50 27 meas. best 8.38
EC50 2 meas. best 5.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.38 5.8493 4.2 14
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 8.07 7.8767 8.5 3
HepG2
CHEMBL395
 IC50 6.67 6.67 214.8 1
MDA-MB-231
CHEMBL400
 IC50 6.46 6.46 349.3 1
Mahlavu
CHEMBL4296473
 IC50 6.16 6.16 700.0 1
MCF7
CHEMBL387
 IC50 5.86 5.86 1384.0 1
Hep 3B2
CHEMBL4296437
 IC50 5.82 5.82 1500.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 5.81 5.81 1550.0 1
Huh-7
CHEMBL614039
 IC50 5.8 5.8 1600.0 1
Aurora kinase B
CHEMBL2185
 IC50 5.75 5.75 1800.0 1
HUVEC
CHEMBL613979
 IC50 5.71 5.71 1954.0 1
Melanocortin receptor 4
CHEMBL259
 IC50 5.35 5.35 4480.0 1
ADMET
CHEMBL612558
 EC50 5.26 5.26 5460.0 1
Neurotensin receptor type 1
CHEMBL4123
 EC50 4.84 4.84 14600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 4.21 nM 8.38 Inhibition of endothelial cord area formation in endothelial precursor cells by ... 22409666
Vascular endothelial growth factor receptor 2 IC50 = 8.5 nM 8.07 Inhibition of N-terminal GST-fused human VEGFR2 C-terminal fragment expressed in... 30108693
Vascular endothelial growth factor receptor 2 IC50 = 12.5 nM 7.9 Inhibition of GST-tagged recombinant human VEGFR2 expressed in Sf9 cells by radi... 24368209
Vascular endothelial growth factor receptor 2 IC50 = 22.0 nM 7.66 Inhibition of recombinant VEGFR2 using poly(Glu,Tyr)4 as substrate assessed as i... 22560627
Unchecked IC50 = 46.8 nM 7.33 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
HepG2 IC50 = 214.8 nM 6.67 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 33002846
MDA-MB-231 IC50 = 349.3 nM 6.46 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 33002846
Unchecked IC50 = 507.5 nM 6.29 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Mahlavu IC50 = 700.0 nM 6.16 Cytotoxicity against human Mahlavu cells assessed as growth inhibition after 72 ... 30108693
Unchecked IC50 = 933.9 nM 6.03 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 1181.3 nM 5.93 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1168.43 nM 5.93 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 1262.7 nM 5.9 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
MCF7 IC50 = 1384.0 nM 5.86 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 33002846
Unchecked IC50 = 1463.7 nM 5.83 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1508.9 nM 5.82 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Hep 3B2 IC50 = 1500.0 nM 5.82 Cytotoxicity against human Hep3B cells assessed as growth inhibition after 72 hr... 30108693
SARS-CoV-2 IC50 = 1550.0 nM 5.81 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
Huh-7 IC50 = 1600.0 nM 5.8 Cytotoxicity against human HuH7 cells assessed as growth inhibition after 72 hrs... 30108693
Aurora kinase B IC50 = 1800.0 nM 5.75 Inhibition of recombinant Aurora B using tetra(LRRWSLG) as substrate assessed as... 22560627

Literature References

PubMed DOI Target Context # Activities
30108693 10.1039/C6MD00392C Huh-7 4
33002846 10.1016/j.ejmech.2020.112851 Unchecked 3
33002846 10.1016/j.ejmech.2020.112851 HUVEC 3
20014752 10.1021/tx900326k Hepatotoxicity 3
30108693 10.1039/C6MD00392C Hep 3B2 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 2
22409666 10.1021/jm201649s Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
22560627 10.1016/j.ejmech.2012.04.007 MCF7 1
22409666 10.1021/jm201649s ADMET 1
38157838 10.1016/j.bmc.2023.117561 Unchecked 1
22560627 10.1016/j.ejmech.2012.04.007 SNB-19 1
22560627 10.1016/j.ejmech.2012.04.007 HT-29 1
22560627 10.1016/j.ejmech.2012.04.007 EKVX 1
22560627 10.1016/j.ejmech.2012.04.007 OVCAR-3 1
22560627 10.1016/j.ejmech.2012.04.007 MDA-MB-435 1
22560627 10.1016/j.ejmech.2012.04.007 Serine/threonine-protein kinase PLK1 1
22560627 10.1016/j.ejmech.2012.04.007 Vascular endothelial growth factor receptor 2 1
22560627 10.1016/j.ejmech.2012.04.007 Focal adhesion kinase 1 1
22560627 10.1016/j.ejmech.2012.04.007 Aurora kinase B 1

Data from ChEMBL 36 via Core Engine