Dasatinib monohydrateProduct ingredient for Dasatinib

Name
Dasatinib monohydrate
Drug Entry
Dasatinib

Dasatinib is an orally available multikinase inhibitor indicated for the treatment of Philadelphia chromosome (Ph)-positive leukemias.1,7 Ph is a chromosomal abnormality found in patients with chronic myelogenous leukemia (CML) and acute lymphocytic leukemia (ALL), where the ABL tyrosine kinase and the breakpoint cluster region (BCR) gene transcribe the chimeric protein BCR-ABL. BCR-ABL is associated with the uncontrolled activity of the ABL tyrosine kinase and is involved in the pathogenesis of CML and 15-30% of ALL cases.5,6 Dasatinib also inhibits a spectrum of kinases involved in cancer, including several SRC-family kinases.5

Unlike imatinib, another tyrosine kinase used for the treatment of CML and Ph-positive ALL, dasatinib inhibits the active and inactive conformations of the ABL kinase domain.2,5 Also, mutations in the kinase domain of BCR-ABL may lead to relapse during imatinib treatment. Since dasatinib does not interact with some of the residues involved in those mutations, the use of this drug represents a therapeutic alternative for patients with cancers that have developed imatinib-resistance.2 The use of dasatinib was first approved by the FDA in 2006.7,9

Accession Number
DBSALT001849
Structure
Synonyms
Dasatinib / Dasatinib hydrate
UNII
RBZ1571X5H
CAS Number
863127-77-9
Weight
Average: 506.02
Monoisotopic: 505.1662867
Chemical Formula
C22H28ClN7O3S
InChI Key
XHXFZZNHDVTMLI-UHFFFAOYSA-N
InChI
InChI=1S/C22H26ClN7O2S.H2O/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);1H2
IUPAC Name
N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide hydrate
SMILES
O.CC1=NC(NC2=NC=C(S2)C(=O)NC2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1
KEGG Drug
D06414
ChemSpider
9715466
ChEBI
70839
Predicted Properties
PropertyValueSource
Water Solubility0.0128 mg/mLALOGPS
logP2.77ALOGPS
logP3.83Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.51Chemaxon
pKa (Strongest Basic)7.18Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area106.51 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity133.08 m3·mol-1Chemaxon
Polarizability52.12 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon