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MedKoo Cat#: 524484 | Name: BMS-509744
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

BMS-509744
BMS-509744
CAS#439575-02-7

Theoretical Analysis

MedKoo Cat#: 524484

Name: BMS-509744

CAS#: 439575-02-7

Chemical Formula: C32H41N5O4S2

Exact Mass: 623.2600

Molecular Weight: 623.83

Elemental Analysis: C, 61.61; H, 6.62; N, 11.23; O, 10.26; S, 10.28

Price and Availability

Size Price Availability Quantity
5mg USD 340.00 2 Weeks
10mg USD 550.00 2 Weeks
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Synonym
BMS-509744; BMS 509744; BMS509744; CHEMBL209148.
IUPAC/Chemical Name
Benzamide, N-(5-((5-((4-acetyl-1-piperazinyl)carbonyl)-4-methoxy-2-methylphenyl)thio)-2-thiazolyl)-4-(((1,2,2-trimethylpropyl)amino)methyl)-
InChi Key
ZHXNIYGJAOPMSO-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
Cc1cc(c(cc1Sc2cnc(s2)NC(=O)c3ccc(cc3)CNC(C)C(C)(C)C)C(=O)N4CCN(CC4)C(=O)C)OC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
BMS-509744 is a potent, selective and ATP competitive Itk inhibitor with an IC50 of 19 nM.
In vitro activity:
Consistent with these results, treatment with the ITK inhibitor BMS-509744 also efficiently inhibited invasion and migration in malignant T cells in a dose- and time-dependent manner (Fig. 3c, d; Additional file 1: Figure S2B). Reference: Cancer Cell Int. 2019; 19: 32. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6376795/
In vivo activity:
Topical application of BMS-509744 to the IMQ-treated skin markedly reduced psoriasis-like skin lesions, such as redness, erythema, scaling, and thickening on day 5. Daily administration of IMQ on the left ear increased the ear thickness in a time-dependent manner (Fig. 1C), and topical application of BMS-509744 significantly reduced the increase in ear thickness on day 5 in IMQ-treated mice. Reference: Biol Pharm Bull. 2021 Apr 1;44(4):528-534. https://pubmed.ncbi.nlm.nih.gov/33473072/
Solvent mg/mL mM comments
Solubility
DMSO 26.6 42.56
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 623.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Liu Y, Wang X, Deng L, Ping L, Shi Y, Zheng W, Lin N, Wang X, Tu M, Xie Y, Liu W, Ying Z, Zhang C, Pan Z, Wang X, Ding N, Song Y, Zhu J. ITK inhibition induced in vitro and in vivo anti-tumor activity through downregulating TCR signaling pathway in malignant T cell lymphoma. Cancer Cell Int. 2019 Feb 14;19:32. doi: 10.1186/s12935-019-0754-9. PMID: 30814910; PMCID: PMC6376795. 2. Otake S, Otsubaki T, Uesato N, Ueda Y, Murayama T, Hayashi M. Topical Application of BMS-509744, a Selective Inhibitor of Interleukin-2-Inducible T Cell Kinase, Ameliorates Imiquimod-Induced Skin Inflammation in Mice. Biol Pharm Bull. 2021 Apr 1;44(4):528-534. doi: 10.1248/bpb.b20-00850. Epub 2021 Jan 20. PMID: 33473072. 3. Lin TA, McIntyre KW, Das J, Liu C, O'Day KD, Penhallow B, Hung CY, Whitney GS, Shuster DJ, Yang X, Townsend R, Postelnek J, Spergel SH, Lin J, Moquin RV, Furch JA, Kamath AV, Zhang H, Marathe PH, Perez-Villar JJ, Doweyko A, Killar L, Dodd JH, Barrish JC, Wityak J, Kanner SB. Selective Itk inhibitors block T-cell activation and murine lung inflammation. Biochemistry. 2004 Aug 31;43(34):11056-62. doi: 10.1021/bi049428r. PMID: 15323564.
In vitro protocol:
1. Liu Y, Wang X, Deng L, Ping L, Shi Y, Zheng W, Lin N, Wang X, Tu M, Xie Y, Liu W, Ying Z, Zhang C, Pan Z, Wang X, Ding N, Song Y, Zhu J. ITK inhibition induced in vitro and in vivo anti-tumor activity through downregulating TCR signaling pathway in malignant T cell lymphoma. Cancer Cell Int. 2019 Feb 14;19:32. doi: 10.1186/s12935-019-0754-9. PMID: 30814910; PMCID: PMC6376795.
In vivo protocol:
1. Otake S, Otsubaki T, Uesato N, Ueda Y, Murayama T, Hayashi M. Topical Application of BMS-509744, a Selective Inhibitor of Interleukin-2-Inducible T Cell Kinase, Ameliorates Imiquimod-Induced Skin Inflammation in Mice. Biol Pharm Bull. 2021 Apr 1;44(4):528-534. doi: 10.1248/bpb.b20-00850. Epub 2021 Jan 20. PMID: 33473072. 2. Lin TA, McIntyre KW, Das J, Liu C, O'Day KD, Penhallow B, Hung CY, Whitney GS, Shuster DJ, Yang X, Townsend R, Postelnek J, Spergel SH, Lin J, Moquin RV, Furch JA, Kamath AV, Zhang H, Marathe PH, Perez-Villar JJ, Doweyko A, Killar L, Dodd JH, Barrish JC, Wityak J, Kanner SB. Selective Itk inhibitors block T-cell activation and murine lung inflammation. Biochemistry. 2004 Aug 31;43(34):11056-62. doi: 10.1021/bi049428r. PMID: 15323564.
1: Dondorf S, Schrader A, Herling M. Interleukin-2-inducible T-cell kinase (ITK) targeting by BMS-509744 does not affect cell viability in T-cell prolymphocytic leukemia (T-PLL). J Biol Chem. 2015 Apr 17;290(16):10568-9. doi: 10.1074/jbc.L115.644641. PubMed PMID: 25888568; PubMed Central PMCID: PMC4400363. 2: Tarafdar S, Poe JA, Smithgall TE. The accessory factor Nef links HIV-1 to Tec/Btk kinases in an Src homology 3 domain-dependent manner. J Biol Chem. 2014 May 30;289(22):15718-28. doi: 10.1074/jbc.M114.572099. Epub 2014 Apr 10. PubMed PMID: 24722985; PubMed Central PMCID: PMC4140925. 3: Kutach AK, Villaseñor AG, Lam D, Belunis C, Janson C, Lok S, Hong LN, Liu CM, Deval J, Novak TJ, Barnett JW, Chu W, Shaw D, Kuglstatter A. Crystal structures of IL-2-inducible T cell kinase complexed with inhibitors: insights into rational drug design and activity regulation. Chem Biol Drug Des. 2010 Aug;76(2):154-63. doi: 10.1111/j.1747-0285.2010.00993.x. Epub 2010 Jun 9. PubMed PMID: 20545945. 4: Lin TA, McIntyre KW, Das J, Liu C, O'Day KD, Penhallow B, Hung CY, Whitney GS, Shuster DJ, Yang X, Townsend R, Postelnek J, Spergel SH, Lin J, Moquin RV, Furch JA, Kamath AV, Zhang H, Marathe PH, Perez-Villar JJ, Doweyko A, Killar L, Dodd JH, Barrish JC, Wityak J, Kanner SB. Selective Itk inhibitors block T-cell activation and murine lung inflammation. Biochemistry. 2004 Aug 31;43(34):11056-62. PubMed PMID: 15323564.