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
- External Links
- Predicted Properties
Property Value Source Water Solubility 0.0128 mg/mL ALOGPS logP 2.77 ALOGPS logP 3.83 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 8.51 Chemaxon pKa (Strongest Basic) 7.18 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 106.51 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 133.08 m3·mol-1 Chemaxon Polarizability 52.12 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon