Dasatinib (CED0001873)

Record Information
Version1.0
Creation Date2016-05-22 04:30:09 UTC
Update Date2026-08-21 22:25:15 UTC
Accession NumberCHEM017626
Identification
Common NameDasatinib
ClassSmall Molecule
Description
Dasatinib is an organic compound with the chemical formula C22H26ClN7O2S and an average molecular weight of 488.01 g/mol. Dasatinib belongs to the anilides, a subclass of benzene and substituted derivatives within the organic compounds. This compound is identified as being found in or released from five recorded sources. These include electrical and electronic equipment, specifically line transmission systems and electric hearing aids, as well as household cleaning and consumer products, including pipe accessories and non-electric simulated smoking devices. Additionally, it is found in healthcare, pharmaceuticals, and veterinary products as an antineoplastic agent. The recorded route of exposure for this substance is oral. Dasatinib acts upon 23 recorded protein targets. It functions as an antagonist, binder, or inhibitor, and is characterized as a multitarget of the proto-oncogene tyrosine-protein kinase Src (SRC), tyrosine-protein kinase ABL1, tyrosine-protein kinase ABL2, and tyrosine-protein kinase Fyn (FYN), along with 19 other proteins.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Anh. dasatinibChEBI
Anhydrous dasatinibChEBI
BMS DasatinibChEBI
BMS-354825ChEBI
Dasatinib (anh.)ChEBI
DasatinibumChEBI
N-(2-CHLORO-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamideChEBI
(18F)-N-(2-Chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamideHMDB
N-(2-Chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamideHMDB
SprycelHMDB
Chemical FormulaC22H26ClN7O2S
Average Molecular Mass488.006 g/mol
Monoisotopic Mass487.156 g/mol
CAS Registry Number302962-49-8
IUPAC NameN-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide
Traditional Namedasatinib
SMILESCC1=NC(NC2=NC=C(S2)C(=O)NC2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1
InChI IdentifierInChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
InChI KeyZBNZXTGUTAYRHI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • Phenylpropane
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.013 g/LALOGPS
logP2.77ALOGPS
logP3.82ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)7.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.51 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity133.08 m³·mol⁻¹ChemAxon
Polarizability51.58 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4j-3104900000-19c063b36c545a5eb85aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00r7-3101490000-d274cb5f2cc0589526f6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000m-0390000000-8a413cb9e53d14cbe10aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0011900000-4dac51b915117532ebe0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0521900000-f036db5f090dc721c061Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0945000000-1344a7f6fa72fda9679cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1941000000-7dd50ec0e4437edbdddbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06ri-0293600000-003749b25fb59315664fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066v-1292100000-f90b69c609d80d3f92a8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-3390000000-0e74e360d8dc98f4adc8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-e70e9316e0f943fd209dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0001900000-009c64fdb2ae58cfd0fbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f72-7395800000-2de6701f9f023ff4fc04Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-25ba0df4df3ee5cf8e03Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fs9-4112900000-d8d24063d0379ec5b337Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-4192000000-f29c2b38b827f08243f6Not 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
2432.0Log mg/kg[1400:4300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
Pathways
2 pathways
Dasatinib Inhibition of BCR-ABL Action Pathway
Dasatinib Inhibition of BCR-ABL Action Pathway
Dasatinib Drug Metabolism Action Pathway
Dasatinib Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)0.0778492
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)0.0778492
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)0.155698
Tyrosine-protein kinase Lyn structureClick to view 3D structureTyrosine-protein kinase LynP07948HumansPredicted (SEA)0.155698
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)0.544945
Tyrosine-protein kinase HCK structureClick to view 3D structureTyrosine-protein kinase HCKP08631HumansPredicted (SEA)0.778492
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)1.47914
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)1.08989
Click to view 3D structureSerine/threonine-protein kinase SIK2Q9H0K1HumansPredicted (SEA)0.544945
Serine/threonine-protein kinase SIK3 structureClick to view 3D structureSerine/threonine-protein kinase SIK3Q9Y2K2HumansPredicted (SEA)0.155698
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)5.29375
Tyrosine-protein kinase Yes structureClick to view 3D structureTyrosine-protein kinase YesP07947HumansPredicted (SEA)1.94623
Tyrosine-protein kinase Fgr structureClick to view 3D structureTyrosine-protein kinase FgrP09769HumansPredicted (SEA)0.544945
Click to view 3D structureSerine/threonine-protein kinase SIK1P57059HumansPredicted (SEA)0.233548
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)9.34191
Macrophage colony-stimulating factor 1 receptor structureClick to view 3D structureMacrophage colony-stimulating factor 1 receptorP07333HumansPredicted (SEA)10.0426
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)9.6533
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)12.5337
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)31.2175
Click to view 3D structureTyrosine-protein kinase BlkP51451HumansPredicted (SEA)13.3901
Click to view 3D structureTyrosine-protein kinase FRKP42685HumansPredicted (SEA)7.70707
Ephrin type-A receptor 2 structureClick to view 3D structureEphrin type-A receptor 2P29317HumansPredicted (SEA)8.48557
Mitogen-activated protein kinase kinase kinase 20 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase 20Q9NYL2HumansPredicted (SEA)5.2159
Protein-tyrosine kinase 6 structureClick to view 3D structureProtein-tyrosine kinase 6Q13882HumansPredicted (SEA)7.62922
Ephrin type-B receptor 4 structureClick to view 3D structureEphrin type-B receptor 4P54760HumansPredicted (SEA)6.15009
Concentrations
Not Available
External Links
DrugBank IDDB01254
HMDB IDHMDB0015384
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDasatinib
Chemspider ID2323020
ChEBI ID49375
PubChem Compound ID3062316
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Talpaz M, Shah NP, Kantarjian H, Donato N, Nicoll J, Paquette R, Cortes J, O'Brien S, Nicaise C, Bleickardt E, Blackwood-Chirchir MA, Iyer V, Chen TT, Huang F, Decillis AP, Sawyers CL: Dasatinib in imatinib-resistant Philadelphia chromosome-positive leukemias. N Engl J Med. 2006 Jun 15;354(24):2531-41.
2. Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, Pang S, Shen DR, Fang Q, de Fex HF, McIntyre KW, Shuster DJ, Gillooly KM, Behnia K, Schieven GL, Wityak J, Barrish JC: 2-aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1- piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J Med Chem. 2006 Nov 16;49(23):6819-32.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16775234
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17154512
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18020922
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18784745
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18797457
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18823558
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19494352
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19502192
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19640584
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21226671
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22411867
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22740998
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22992064
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23065516