BMS-509744
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 524484

CAS#: 439575-02-7

Description: 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

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BMS-509744
CAS# 439575-02-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 524484
Name: BMS-509744
CAS#: 439575-02-7
Chemical Formula: C32H41N5O4S2
Exact Mass: 623.26
Molecular Weight: 623.830
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 2 Weeks
10mg USD 530 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:
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 26.6 42.56

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.

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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.