dasatinib   Click here for help

GtoPdb Ligand ID: 5678

Synonyms: BMS 345825 | BMS 354825 | BMS 35482513 | Sprycel®
Approved drug PDB Ligand Immunopharmacology Ligand
dasatinib is an approved drug (FDA & EMA (2006))
Compound class: Synthetic organic
Comment: Dasatinib is a Type-1 kinase inhibitor and was first approved by the FDA in 2006.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: dasatinib

dasatinib is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 134.75
Molecular weight 487.16
XLogP 1.99
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCCN1CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(C)cccc1Cl
Isomeric SMILES OCCN1CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(C)cccc1Cl
InChI InChI=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 Key ZBNZXTGUTAYRHI-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2006))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide
International Nonproprietary Names Click here for help
INN number INN
8712 dasatinib
Synonyms Click here for help
BMS 345825 | BMS 354825 | BMS 35482513 | Sprycel®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9669723
Reactome Reaction Reactome logo R-HSA-9674430, R-HSA-9674095, R-HSA-9669900, R-HSA-9669855, R-HSA-9669854
Other databases
CAS Registry No. 302962-49-8
ChEMBL Ligand CHEMBL1421
DrugBank Ligand DB01254
DrugCentral Ligand 785
GtoPdb PubChem SID 178102305
PubChem CID 3062316
RCSB PDB Ligand 1N1
Search Google for chemical match using the InChIKey ZBNZXTGUTAYRHI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ZBNZXTGUTAYRHI
Search PubMed clinical trials dasatinib
Search PubMed titles dasatinib
Search PubMed titles/abstracts dasatinib
SynPHARM 78746 (in complex with ABL proto-oncogene 1, non-receptor tyrosine kinase)
UniChem Compound Search for chemical match using the InChIKey ZBNZXTGUTAYRHI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZBNZXTGUTAYRHI-UHFFFAOYSA-N
Wikipedia Dasatinib

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Tocris
Dasatinib (links to external site)
Cat. No. 6793