Dasatinib monolauryl sulfateProduct ingredient for Dasatinib

Name
Dasatinib monolauryl sulfate
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
DBSALT003471
Structure
Synonyms
Dasatinib laurylsulfate
External IDs
C078D
UNII
FY77PS0C4O
CAS Number
2398469-56-0
Weight
Average: 754.4
Monoisotopic: 753.3109025
Chemical Formula
C34H52ClN7O6S2
InChI Key
SWMPKFFMQAIAEW-UHFFFAOYSA-N
InChI
InChI=1S/C22H26ClN7O2S.C12H26O4S/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;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27);2-12H2,1H3,(H,13,14,15)
IUPAC Name
(Z)-N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboximidic acid; (dodecyloxy)sulfonic acid
SMILES
CCCCCCCCCCCCOS(O)(=O)=O.CC1=NC(NC2=NC=C(S2)C(\O)=N\C2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1
Not Available
Predicted Properties
PropertyValueSource
logP1.87Chemaxon
pKa (Strongest Acidic)2.89Chemaxon
pKa (Strongest Basic)8.14Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area110 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity133.83 m3·mol-1Chemaxon
Polarizability52.4 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon