Selumetinib (CED0003463)

Record Information
Version1.0
Creation Date2016-05-22 06:51:37 UTC
Update Date2026-08-19 18:45:15 UTC
Accession NumberCHEM020161
Identification
Common NameSelumetinib
ClassSmall Molecule
Description
Selumetinib belongs to the benzimidazoles, a class of organoheterocyclic compounds within the organic compounds. It has a chemical formula of C17H15BrClFN4O3 and an average molecular weight of 457.68 g/mol. This compound is found in or released from two recorded sources: electrical and electronic equipment, specifically electric hearing aids, and healthcare, pharmaceuticals and veterinary products, specifically antineoplastic agents. The recorded route of exposure for this substance is oral. At the molecular level, selumetinib acts on two recorded protein targets, serving as an inhibitor of dual specificity mitogen-activated protein kinase kinase 1 (MAP2K1) and dual specificity mitogen-activated protein kinase kinase 2 (MAP2K2). Regarding its health effects, selumetinib is used as a treatment for breast cancer (PMC11537572). Additionally, the compound is noted to have a therapeutic effect on pain (PMC7609673).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ARRY 142886ChEBI
ARRY-142886ChEBI
ARRY142886ChEBI
AZD 6244ChEBI
AZD-6244ChEBI
AZD6244ChEBI
SelumetinibumChEBI
SelumetinibMeSH
Chemical FormulaC17H15BrClFN4O3
Average Molecular Mass457.680 g/mol
Monoisotopic Mass456.000 g/mol
CAS Registry Number606143-52-6
IUPAC Name5-[(4-bromo-2-chlorophenyl)amino]-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-1,3-benzodiazole-6-carboximidic acid
Traditional Name6-[(4-bromo-2-chlorophenyl)amino]-7-fluoro-N-(2-hydroxyethoxy)-3-methyl-1,3-benzodiazole-5-carboximidic acid
SMILESCN1C=NC2=C1C=C(C(O)=NOCCO)C(NC1=C(Cl)C=C(Br)C=C1)=C2F
InChI IdentifierInChI=1S/C17H15BrClFN4O3/c1-24-8-21-16-13(24)7-10(17(26)23-27-5-4-25)15(14(16)20)22-12-3-2-9(18)6-11(12)19/h2-3,6-8,22,25H,4-5H2,1H3,(H,23,26)
InChI KeyCYOHGALHFOKKQC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Aniline or substituted anilines
  • Bromobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Secondary amine
  • Organooxygen compound
  • Primary alcohol
  • Organohalogen compound
  • Organobromide
  • Amine
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP3.73ALOGPS
logP3.41ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.49ChemAxon
pKa (Strongest Basic)5.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area91.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.13 m³·mol⁻¹ChemAxon
Polarizability41.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-5003900000-ad7092eb9e18e8c63f94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2009100000-3858abbf1afdf7e8f6f3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-9006000000-a56224b65db84bc5eb20Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1002900000-035bcb0c187f51cde944Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udl-4009400000-abdf560a6933bf91112dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ug0-4229000000-d09a5ee27c45ba878051Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000900000-73d7e6711f3af0f387fcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053r-0009800000-9075ace0cdf9bf6369a0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0139100000-acd888a1944907e50ac2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0001900000-37aa71a8f8f030f74806Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-4009500000-567c825d54ceb9e7e6a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-3009000000-6f51161796301c9b94b6Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3292.0Log mg/kg[1900:5900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
breast canceris_treatment_forNot AvailablePMC11537572
painhas_therapeutic_effect_onNot AvailablePMC7609673
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Selumetinib Drug Metabolism Action Pathway
Selumetinib Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Dual specificity mitogen-activated protein kinase kinase 1 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 1Q02750HumansPredicted (SEA)167.999
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)398.121
Serine/threonine-protein kinase B-raf structureClick to view 3D structureSerine/threonine-protein kinase B-rafP15056HumansPredicted (SEA)184.503
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)581.3
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)671.761
Dual specificity mitogen-activated protein kinase kinase 2 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 2P36507HumansPredicted (SEA)175.005
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)346.585
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)571.647
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)381.85
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)400.69
High affinity nerve growth factor receptor structureClick to view 3D structureHigh affinity nerve growth factor receptorP04629HumansPredicted (SEA)483.21
Mitogen-activated protein kinase 3 structureClick to view 3D structureMitogen-activated protein kinase 3P27361HumansPredicted (SEA)124.092
Dual specificity mitogen-activated protein kinase kinase 5 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 5Q13163HumansPredicted (SEA)124.948
Insulin receptor structureClick to view 3D structureInsulin receptorP06213HumansPredicted (SEA)427.159
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)594.067
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)656.658
BDNF/NT-3 growth factors receptor structureClick to view 3D structureBDNF/NT-3 growth factors receptorQ16620HumansPredicted (SEA)455.885
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)519.721
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)448.334
Tyrosine-protein kinase BTK structureClick to view 3D structureTyrosine-protein kinase BTKQ06187HumansPredicted (SEA)591.654
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)744.628
Dual specificity protein kinase TTK structureClick to view 3D structureDual specificity protein kinase TTKP33981HumansPredicted (SEA)156.944
Cyclin-dependent kinase 5 structureClick to view 3D structureCyclin-dependent kinase 5Q00535HumansPredicted (SEA)482.587
Mitogen-activated protein kinase kinase kinase kinase 1 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase kinase 1Q92918HumansPredicted (SEA)137.092
Structural maintenance of chromosomes protein 1A structureClick to view 3D structureStructural maintenance of chromosomes protein 1AQ14683HumansPredicted (SEA)0.311397
Concentrations
Not Available
External Links
DrugBank IDDB11689
HMDB IDHMDB0304858
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSelumetinib
Chemspider ID8303141
ChEBI ID90227
PubChem Compound ID10127622
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20407895
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20978926
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21594619
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22241789
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22343622
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22394161
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22565394
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22972589
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23372439
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23444215
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23942066
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=25322874
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25342139
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25379021
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25385055
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25498501
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25637165
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=25887099
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=26059332
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=26384399
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=26446942