Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C32H41N5O4S2 |
| Molecular Weight | 623.829 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(C=C(SC2=CN=C(NC(=O)C3=CC=C(CNC(C)C(C)(C)C)C=C3)S2)C(C)=C1)C(=O)N4CCN(CC4)C(C)=O
InChI
InChIKey=ZHXNIYGJAOPMSO-UHFFFAOYSA-N
InChI=1S/C32H41N5O4S2/c1-20-16-26(41-7)25(30(40)37-14-12-36(13-15-37)22(3)38)17-27(20)42-28-19-34-31(43-28)35-29(39)24-10-8-23(9-11-24)18-33-21(2)32(4,5)6/h8-11,16-17,19,21,33H,12-15,18H2,1-7H3,(H,34,35,39)
| Molecular Formula | C32H41N5O4S2 |
| Molecular Weight | 623.829 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
BMS-509744 is a potent interleukin-2 inducible T cell kinase (ITK) inhibitor (IC50 = 19 nM). It displays 200-fold selectivity over Tec family kinases and 55-fold selectivity over other kinases tested. BMS-509744 reduces HIV infection of primary CD4+ T cells and attenuates the establishment of HIV infection in vitro. BMS-509744 also reduces T cell proliferation and IL-2 production in vitro. BMS-509744 reduces TCR-induced functions including PLCgamma1 tyrosine phosphorylation, calcium mobilization, IL-2 secretion, and T-cell proliferation in vitro in both human and mouse cells. BMS-509744 suppresses the production of IL-2 induced by anti-TCR antibody administered to mice. BMS-509744 also significantly diminishes lung inflammation in a mouse model of ovalbumin-induced allergy/asthma.
Originator
Sources: http://adisinsight.springer.com/drugs/800018631 | https://www.ncbi.nlm.nih.gov/pubmed/15323564
Curator's Comment: # Bristol-Myers Squibb
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Selective Itk inhibitors block T-cell activation and murine lung inflammation. | 2004 Aug 31 |
|
| Crystal structures of IL-2-inducible T cell kinase complexed with inhibitors: insights into rational drug design and activity regulation. | 2010 Aug |
|
| The accessory factor Nef links HIV-1 to Tec/Btk kinases in an Src homology 3 domain-dependent manner. | 2014 May 30 |
|
| Interleukin-2-inducible T-cell kinase (ITK) targeting by BMS-509744 does not affect cell viability in T-cell prolymphocytic leukemia (T-PLL). | 2015 Apr 17 |
Sample Use Guides
Murine Lung Inflammation Model: BMS-509744 dose-dependently reduced lung inflammation in these mice as a function of a reduction in both total cell and eosinophil infiltration into the lung. The reduction
reached statistical significance at doses of 25 mg/kg administered subcutaneously, twice daily for 3 days, starting
at the time of the ovalbumin inhalation challenge.
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:23:12 GMT 2023
by
admin
on
Sat Dec 16 09:23:12 GMT 2023
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| Record UNII |
5V7VG25953
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| Record Status |
Validated (UNII)
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| Record Version |
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