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Details

Stereochemistry ACHIRAL
Molecular Formula C16H14BrN3O3
Molecular Weight 376.205
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WHI-P 154

SMILES

COC1=C(OC)C=C2C(NC3=CC(Br)=C(O)C=C3)=NC=NC2=C1

InChI

InChIKey=CBIAKDAYHRWZCU-UHFFFAOYSA-N
InChI=1S/C16H14BrN3O3/c1-22-14-6-10-12(7-15(14)23-2)18-8-19-16(10)20-9-3-4-13(21)11(17)5-9/h3-8,21H,1-2H3,(H,18,19,20)

HIDE SMILES / InChI

Molecular Formula C16H14BrN3O3
Molecular Weight 376.205
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/9796979 | https://www.ncbi.nlm.nih.gov/pubmed/27119652

WHI-P154 is an inhibitor of Janus-activated kinase JAK3. Also this drug inhibits other common kinases including EGFR, Src, Abl, VEGFR and others. WHI-P154 is potent inhibitor of glioblastoma cell adhesion and migration. Further preclinical development of WHI-P154 may provide the basis for the design of more effective adjuvant chemotherapy programs for glioblastoma multiforme. Treatment of ALK inhibitor, WHI-P154 resulted in the down-regulation of aberrant anaplastic lymphoma kinase (ALK) signaling, shrinkage of tumor, and suppression of metastasis and significantly improved survival of ALK mutant-bearing mice.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
4-(3'-Bromo-4'hydroxylphenyl)-amino-6,7-dimethoxyquinazoline: a novel quinazoline derivative with potent cytotoxic activity against human glioblastoma cells.
1998 Jun
Inhibition of human glioblastoma cell adhesion and invasion by 4-(4'-hydroxylphenyl)-amino-6,7-dimethoxyquinazoline (WHI-P131) and 4-(3'-bromo-4'-hydroxylphenyl)-amino-6,7-dimethoxyquinazoline (WHI-P154).
1998 Oct
The specificity of JAK3 kinase inhibitors.
2008 Feb 15
Janus kinase 3 inhibitor WHI-P154 in macrophages activated by bacterial endotoxin: differential effects on the expression of iNOS, COX-2 and TNF-alpha.
2008 Jan
Differential regulation of proliferation and differentiation in neural precursor cells by the Jak pathway.
2010 Oct
Patents

Sample Use Guides

Mouse: 1 mg/kg per day
Route of Administration: Intravenous
In Vitro Use Guide
WHI-P154 exhibited significant cytotoxicity against the U373 human glioblastoma cell line in three of three independent experiments with a mean (± SE) IC50 of 167.4 uM and a composite survival curve IC50 of 158.5 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:57:11 GMT 2023
Edited
by admin
on Sat Dec 16 11:57:11 GMT 2023
Record UNII
PG8BT6T9MB
Record Status Validated (UNII)
Record Version
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Name Type Language
WHI-P 154
Common Name English
2-BROMO-4-((6,7-DIMETHOXY-4-QUINAZOLINYL)AMINO)PHENOL
Systematic Name English
JAK3 INHIBITOR II
Common Name English
PHENOL, 2-BROMO-4-((6,7-DIMETHOXY-4-QUINAZOLINYL)AMINO)-
Systematic Name English
4-(3'-BROMO-4'-HYDROXYPHENYL)AMINO-6,7-DIMETHOXYQUINAZOLINE
Systematic Name English
Code System Code Type Description
FDA UNII
PG8BT6T9MB
Created by admin on Sat Dec 16 11:57:11 GMT 2023 , Edited by admin on Sat Dec 16 11:57:11 GMT 2023
PRIMARY
PUBCHEM
3795
Created by admin on Sat Dec 16 11:57:11 GMT 2023 , Edited by admin on Sat Dec 16 11:57:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID60274407
Created by admin on Sat Dec 16 11:57:11 GMT 2023 , Edited by admin on Sat Dec 16 11:57:11 GMT 2023
PRIMARY
CAS
211555-04-3
Created by admin on Sat Dec 16 11:57:11 GMT 2023 , Edited by admin on Sat Dec 16 11:57:11 GMT 2023
PRIMARY
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IC50