P30

1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-{7-[2-(morpholin-4-yl)ethoxy]imidazo[2,1-b][1,3]benzothiazol-2-yl}phenyl)urea

Created:2014-11-14
Last modified:  2020-05-27

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Chemical Details

Formal Charge0
Atom Count72
Chiral Atom Count0
Bond Count77
Aromatic Bond Count25
2D diagram of P30

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Chemical Component Summary

Name1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-{7-[2-(morpholin-4-yl)ethoxy]imidazo[2,1-b][1,3]benzothiazol-2-yl}phenyl)urea
SynonymsQuizartinib; PLX3397
Systematic Name (OpenEye OEToolkits)1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[6-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl]urea
FormulaC29 H32 N6 O4 S
Molecular Weight560.667
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs12.01O=C(Nc1noc(c1)C(C)(C)C)Nc6ccc(c4nc5sc3c(ccc(OCCN2CCOCC2)c3)n5c4)cc6
SMILESCACTVS3.385CC(C)(C)c1onc(NC(=O)Nc2ccc(cc2)c3cn4c(sc5cc(OCCN6CCOCC6)ccc45)n3)c1
SMILESOpenEye OEToolkits1.7.6CC(C)(C)c1cc(no1)NC(=O)Nc2ccc(cc2)c3cn4c5ccc(cc5sc4n3)OCCN6CCOCC6
Canonical SMILESCACTVS3.385 CC(C)(C)c1onc(NC(=O)Nc2ccc(cc2)c3cn4c(sc5cc(OCCN6CCOCC6)ccc45)n3)c1
Canonical SMILESOpenEye OEToolkits1.7.6 CC(C)(C)c1cc(no1)NC(=O)Nc2ccc(cc2)c3cn4c5ccc(cc5sc4n3)OCCN6CCOCC6
InChIInChI1.03 InChI=1S/C29H32N6O4S/c1-29(2,3)25-17-26(33-39-25)32-27(36)30-20-6-4-19(5-7-20)22-18-35-23-9-8-21(16-24(23)40-28(35)31-22)38-15-12-34-10-13-37-14-11-34/h4-9,16-18H,10-15H2,1-3H3,(H2,30,32,33,36)
InChIKeyInChI1.03 CVWXJKQAOSCOAB-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB12874 
NameQuizartinib
Groups
  • investigational
  • approved
DescriptionQuizartinib is an oral and potent fms-like tyrosine kinase 3 (FLT3) inhibitor and it is the first drug developed specifically targeting FLT3, as other agents with FLT3 inhibition activities were investigated with other targets in mind.[A260641] Additionally, quizartinib also demonstrates inhibitory activity toward FLT3 with internal tandem duplication (ITD), although with a 10-fold lower affinity compared to wild-type FLT3.[L47426] FLT3-ITD mutation is present in 75% of FLT3-mutated AML, leading to constitutively active FLT3 and thus poorer overall survival and higher risk of relapse.[A260646] Multiple clinical trials have demonstrated quizartinib's efficacy in relapsed/refractory FLT3-ITD mutant AML.[A260651] Therefore, quizartinib is proven to be a beneficial addition to the current AML treatment regimen, although serious side effects such as QT prolongation necessitates further research to optimize quizartinib's addition to AML standard of care.[A260641] Quizartinib was approved by the FDA in July 2023 and developed under the brand name VANFLYTA by Daiichi Sankyo.[L47436] The FDA approval was based on positive results from the QuANTUM-First trial for FLT3-ITD positive AML, where quizartinib combined with standard cytarabine and anthracycline induction and standard cytarabine consolidation, followed by a maintenance monotherapy resulted in a 22% reduction in the risk of death.[L47436]
Synonyms
  • Quizartinib dihydrochloride
  • Quizartinib
  • Quizartinibum
  • N-(5-(1,1-Dimethylethyl)isoxazol-3-yl)-N'-(4-(7-(2-(morpholin-4-yl)ethoxy)imidazo(2,1-b)benzothiazol-2-yl)phenyl)urea
Brand NamesVanflyta
IndicationQuizartinib is indicated in combination with standard cytarabine and anthracycline induction and cytarabine consolidation, and as maintenance monotherapy following consolidation chemotherapy, for the treatment of adult patients with newly diagnosed acute myeloid leukemia (AML) that is FLT3 internal tandem duplication (ITD)-positive as detected by an FDA-approved test.[L47426]
Categories
  • Amides
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Inhibitors
  • Benzene Derivatives
ATC-CodeL01EX11
CAS number950769-58-1

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Receptor-type tyrosine-protein kinase FLT3MPALARDGGQLPLLVVFSAMIFGTITNQDLPVIKCVLINHKNNDSSVGKS...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
UDP-glucuronosyltransferase 1A1MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...unknowninhibitor
Cytochrome P450 3A7MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL576982
PubChem 24889392
ChEMBL CHEMBL576982
ChEBI CHEBI:90217