BMS-935177 | CAS#1231889-53-4 | BTK inhibitor

MedKoo Cat#: 526843 | Name: BMS-935177

Description:

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

BMS-935177 a potent BTK inhibitor with improved kinase selectivity and superior oral exposure in multiple species. should provide useful clinical efficacy in autoimmune diseases. BMS-935177 inhibited calcium flux in human Ramos B cells (IC50 = 27 nM) and inhibited CD69 surface expression in peripheral B cells stimulated with anti-IgM and anti-IgG. On the basis of in vitro potency, in vivo activity, and pharmacokinetic profile, BMS-935177 was selected for further studies in support of clinical development.

Chemical Structure

BMS-935177

CAS#1231889-53-4

Theoretical Analysis

MedKoo Cat#: 526843

Name: BMS-935177

CAS#: 1231889-53-4

Chemical Formula: C31H26N4O3

Exact Mass: 502.2005

Molecular Weight: 502.57

Elemental Analysis: C, 74.09; H, 5.21; N, 11.15; O, 9.55

Price and Availability

Size	Price	Availability
100mg	USD 1,650.00	2 Weeks
200mg	USD 2,450.00	2 Weeks
500mg	USD 3,650.00	2 Weeks
1g	USD 4,850.00	2 Weeks
2g	USD 8,250.00	2 Weeks

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Synonym

BMS-935177; BMS 935177; BMS935177.

IUPAC/Chemical Name

7-(2-hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9H-carbazole-1-carboxamide

InChi Key

TVJRDCQUZMGBAB-UHFFFAOYSA-N

InChi Code

InChI=1S/C31H26N4O3/c1-17-19(8-6-10-26(17)35-16-33-24-9-5-4-7-22(24)30(35)37)20-13-14-23(29(32)36)28-27(20)21-12-11-18(31(2,3)38)15-25(21)34-28/h4-16,34,38H,1-3H3,(H2,32,36)

SMILES Code

O=C(C1=CC=C(C2=CC=CC(N3C(C4=C(C=CC=C4)N=C3)=O)=C2C)C5=C1NC6=C5C=CC(C(C)(O)C)=C6)N

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

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

Bruton’s tyrosine kinase (BTK) belongs to the TEC family of nonreceptor tyrosine kinases and plays a critical role in multiple cell types responsible for numerous autoimmune diseases.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

BMS-935177 is a potent and selective reversible inhibitor of Bruton’s tyrosine kinase (Btk) with an IC50 of 3 nM.

In vitro activity:

Compound 6 (BMS-935177) (inhibited calcium flux in human Ramos B cells (IC50 = 27 nM) and inhibited CD69 surface expression in peripheral B cells stimulated with anti-IgM and anti-IgG. Reference: J Med Chem. 2016 Sep 8;59(17):7915-35. https://pubmed.ncbi.nlm.nih.gov/27531604/

In vivo activity:

In the KLH assay, 6 (BMS-935177) (showed superior in vivo potency compared to 14. As shown in Figure 5A, when dosed orally once daily at 5, 20, and 45 mg/kg to mice, the compound inhibited anti-KLH antibodies of the IgG isotype at day 14, with statistically significant reductions at all doses. Reference: J Med Chem. 2016 Sep 8;59(17):7915-35. https://pubmed.ncbi.nlm.nih.gov/27531604/

	Solvent	mg/mL	mM
Solubility
	DMSO	115.0	228.82
	Ethanol	100.0	198.98

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 502.57 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.

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. De Lucca GV, Shi Q, Liu Q, Batt DG, Beaudoin Bertrand M, Rampulla R, Mathur A, Discenza L, D'Arienzo C, Dai J, Obermeier M, Vickery R, Zhang Y, Yang Z, Marathe P, Tebben AJ, Muckelbauer JK, Chang CJ, Zhang H, Gillooly K, Taylor T, Pattoli MA, Skala S, Kukral DW, McIntyre KW, Salter-Cid L, Fura A, Burke JR, Barrish JC, Carter PH, Tino JA. Small Molecule Reversible Inhibitors of Bruton's Tyrosine Kinase (BTK): Structure-Activity Relationships Leading to the Identification of 7-(2-Hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9H-carbazole-1-carboxamide (BMS-935177). J Med Chem. 2016 Sep 8;59(17):7915-35. doi: 10.1021/acs.jmedchem.6b00722. Epub 2016 Aug 26. PMID: 27531604.

In vitro protocol:

In vivo protocol:

Small Molecule Reversible Inhibitors of Bruton’s Tyrosine Kinase (BTK): Structure–Activity Relationships Leading to the Identification of 7-(2-Hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9H-carbazole-1-carboxamide (BMS-935177) George V. De Lucca, Qing Shi, Qingjie Liu, Douglas G. Batt, Myra Beaudoin Bertrand, Rick Rampulla, Arvind Mathur, Lorell Discenza, Celia D’Arienzo, Jun Dai, Mary Obermeier, Rodney Vickery, Yingru Zhang, Zheng Yang, Punit Marathe, Andrew J. Tebben, Jodi K. Muckelbauer, ChiehYing J. Chang, Huiping Zhang, Kathleen Gillooly, Tracy Taylor, Mark A. Pattoli, Stacey Skala, Daniel W. Kukral, Kim W. McIntyre, Luisa Salter-Cid, Aberra Fura, James R. Burke, Joel C. Barrish, Percy H. Carter, and Joseph A. Tino Publication Date (Web): August 17, 2016 (Article) DOI: 10.1021/acs.jmedchem.6b00722