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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL535
CHEMBL535
Compound Name SUNITINIB
ChEMBL Synonyms SUTENT | SUNITINIB | Sutent | SU-11248 | SUNITINIB MALATE
Max Phase 4 (Approved)
Trade Names SUTENT | SUNITINIB MALATE
Molecular Formula C22H27FN4O2

Additional synonyms for CHEMBL535 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCN(CC)CCNC(=O)c1c(C)[nH]c(\C=C\2/C(=O)Nc3ccc(F)cc23)c1C
Standard InChI InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25 ...
Download InChI
Standard InChI Key WINHZLLDWRZWRT-ATVHPVEESA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL535

Molecule Features

CHEMBL535 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Macrophage colony stimulating factor receptor inhibitor Macrophage colony stimulating factor receptor DailyMed
Platelet-derived growth factor receptor inhibitor Platelet-derived growth factor receptor DailyMed
Stem cell growth factor receptor inhibitor Stem cell growth factor receptor DailyMed
Tyrosine-protein kinase receptor FLT3 inhibitor Tyrosine-protein kinase receptor FLT3 DailyMed
Tyrosine-protein kinase receptor RET inhibitor Tyrosine-protein kinase receptor RET DailyMed
Vascular endothelial growth factor receptor inhibitor Vascular endothelial growth factor receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AscitesD001201HP:0001541Ascites2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma2ClinicalTrials
Gastrointestinal Stromal TumorsD046152Orphanet:44890Gastrointestinal stromal tumor4ClinicalTrials
DailyMed
ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor2ClinicalTrials
ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma2ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma2ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
ClinicalTrials
Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm2ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia1ClinicalTrials
ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000196metastatic prostate cancer3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials
ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma2ClinicalTrials
ClinicalTrials
ThymomaD013945EFO:1000581Thymoma2ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma2ClinicalTrials
ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000349clear cell renal carcinoma4ClinicalTrials
ClinicalTrials
CholangiocarcinomaD018281EFO:0005221cholangiocarcinoma2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma2ClinicalTrials
ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma2ClinicalTrials
Inflammatory Breast NeoplasmsD058922EFO:1000984inflammatory breast carcinoma2ClinicalTrials
Kidney NeoplasmsD007680EFO:0003865kidney neoplasm3ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Urethral NeoplasmsD014523EFO:0003846urethral neoplasm2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma4ClinicalTrials
ClinicalTrials
DailyMed
MelanomaD008545EFO:0000756melanoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000640papillary renal cell carcinoma4ClinicalTrials
OligodendrogliomaD009837EFO:0000632oligodendroglioma2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
ClinicalTrials
Sarcoma, KaposiD012514EFO:0000558Kaposi's sarcoma2ClinicalTrials
Adrenocortical CarcinomaD018268EFO:0003093adrenocortical carcinoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
ClinicalTrials
Hemorrhagic Fever, EbolaD019142EFO:0007243Ebola hemorrhagic fever1ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma2ClinicalTrials
ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma2ClinicalTrials
Neuroendocrine TumorsD018358EFO:1000045pancreatic neuroendocrine tumor4DailyMed
AdenocarcinomaD000230EFO:0000228adenocarcinoma2ClinicalTrials
Carcinoid TumorD002276EFO:0004243carcinoid tumor2ClinicalTrials
Carcinoma, Islet CellD018273EFO:0007416pancreatic endocrine carcinoma3ClinicalTrials
ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma4ClinicalTrials
ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma2ClinicalTrials
ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma3ClinicalTrials
ClinicalTrials
Sarcoma, Alveolar Soft PartD018234EFO:0007143alveolar soft part sarcoma2ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000294bladder tumor2ClinicalTrials
von Hippel-Lindau DiseaseD006623Orphanet:892Von Hippel-Lindau disease2ClinicalTrials
ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Ovarian NeoplasmsD010051Orphanet:398934Malignant epithelial tumor of ovary2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Stomach NeoplasmsD013274EFO:0003897stomach neoplasm2ClinicalTrials
ClinicalTrials
Urogenital NeoplasmsD014565EFO:0003863urogenital neoplasm2ClinicalTrials
Adenocarcinoma, FollicularD018263EFO:0000501follicular thyroid carcinoma2ClinicalTrials
Fallopian Tube NeoplasmsD005185EFO:1000251Fallopian Tube Carcinoma2ClinicalTrials
OligodendrogliomaD009837EFO:0000630oligoastrocytoma2ClinicalTrials
Peritoneal NeoplasmsD010534EFO:1001100peritoneal neoplasm2ClinicalTrials
Thyroid NeoplasmsD013964EFO:0000641papillary thyroid carcinoma2ClinicalTrials

Clinical Data

ClinicalTrials.gov SUNITINIB
The Cochrane Collaboration SUNITINIB

Metabolites for CHEMBL535

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL535. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1913 Platelet-derived growth factor receptor beta Homo sapiens 1.000
CHEMBL2007 Platelet-derived growth factor receptor alpha Homo sapiens 1.000
CHEMBL2073 Tyrosine-protein kinase YES Homo sapiens 1.000
CHEMBL1936 Stem cell growth factor receptor Homo sapiens 1.000
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 1.000
CHEMBL4525 Serine/threonine-protein kinase 17A Homo sapiens 1.000
CHEMBL3935 Serine/threonine-protein kinase Aurora-C Homo sapiens 1.000
CHEMBL3980 Serine/threonine-protein kinase 17B Homo sapiens 1.000
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 1.000
CHEMBL3650 Fibroblast growth factor receptor 1 Homo sapiens 1.000
CHEMBL2793 Casein kinase I alpha Homo sapiens 1.000
CHEMBL3788 Serine/threonine-protein kinase PLK4 Homo sapiens 1.000
CHEMBL3835 Serine/threonine-protein kinase NEK2 Homo sapiens 0.999
CHEMBL1974 Tyrosine-protein kinase receptor FLT3 Homo sapiens 0.998
CHEMBL6005 Serine/threonine-protein kinase 33 Homo sapiens 0.996
CHEMBL1955 Vascular endothelial growth factor receptor 3 Homo sapiens 0.993
CHEMBL2468 Death-associated protein kinase 3 Homo sapiens 0.992
CHEMBL4948 Dual specificity mitogen-activated protein kinase kinase 5 Homo sapiens 0.991
CHEMBL279 Vascular endothelial growth factor receptor 2 Homo sapiens 0.977
CHEMBL3055 Cyclin-dependent kinase 7 Homo sapiens 0.956



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1913 Platelet-derived growth factor receptor beta Homo sapiens 1.000
CHEMBL2007 Platelet-derived growth factor receptor alpha Homo sapiens 1.000
CHEMBL3516 Vascular endothelial growth factor receptor 1 Mus musculus 1.000
CHEMBL3650 Fibroblast growth factor receptor 1 Homo sapiens 1.000
CHEMBL2073 Tyrosine-protein kinase YES Homo sapiens 1.000
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 1.000
CHEMBL1936 Stem cell growth factor receptor Homo sapiens 1.000
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 1.000
CHEMBL4525 Serine/threonine-protein kinase 17A Homo sapiens 1.000
CHEMBL3935 Serine/threonine-protein kinase Aurora-C Homo sapiens 1.000
CHEMBL3788 Serine/threonine-protein kinase PLK4 Homo sapiens 1.000
CHEMBL4597 Serine/threonine-protein kinase PCTAIRE-1 Homo sapiens 1.000
CHEMBL3980 Serine/threonine-protein kinase 17B Homo sapiens 1.000
CHEMBL5785 Interferon-induced, double-stranded RNA-activated protein kinase Homo sapiens 1.000
CHEMBL2558 Death-associated protein kinase 1 Homo sapiens 0.999
CHEMBL2543 Casein kinase I gamma 2 Homo sapiens 0.999
CHEMBL3032 Protein kinase N2 Homo sapiens 0.998
CHEMBL2468 Death-associated protein kinase 3 Homo sapiens 0.997
CHEMBL3125 Ribosomal protein S6 kinase alpha 4 Homo sapiens 0.997
CHEMBL3830 Adaptor-associated kinase Homo sapiens 0.996

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
398.5 398.2118 3.33 7 77.23 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 3 0 6 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.7 9.09 2.27 .44 2 29 0.63

Structural Alerts

There are 4 structural alerts for CHEMBL535. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XE - Protein kinase inhibitors
L01XE04 - sunitinib

ChemSpider ChemSpider:WINHZLLDWRZWRT-ATVHPVEESA-N
DailyMed sunitinib malate
PubChem SID: 124893176 SID: 26758053 SID: 50100120
Wikipedia Sunitinib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL535



BindingDB 4814
Brenda 127384 40342 7646 25420
ChEBI 38940
ChemicalBook CB9728174
DrugBank DB01268
DrugCentral 2544
eMolecules 23296409 27524016
FDA SRS V99T50803M
Guide to Pharmacology 5713
Human Metabolome Database HMDB0015397
IBM Patent System E15A9C477969D7725F2513D18EAF49DF
LINCS LSM-42800
MolPort MolPort-006-167-758
Nikkaji J1.942.549E J2.036.576E
PDBe B49
PharmGKB PA162372840
PubChem 5329102
PubChem: Thomson Pharma 14830382
SureChEMBL SCHEMBL8081
ZINC ZINC000003964325

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/WINHZLLDWRZWRT-ATVHPVEESA-N spacer
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