253174-92-4

253174-92-4 structure

Name: BMS-262084
Chemical Name: (2S,3R)-1-[4-(tert-butylcarbamoyl)piperazine-1-carbonyl]-3-[3-(diaminomethylideneamino)propyl]-4-oxoazetidine-2-carboxylic acid
CAS Number: 253174-92-4
Molecular Formula: C₁₈H₃₁N₇O₅
Molecular Weight: 425.48300
Catalog: Signaling Pathways Metabolic Enzyme/Protease Factor Xa
Create Date: 2016-07-11 23:37:18
Modify Date: 2024-01-04 00:27:06
BMS-262084 is a potent, selective and irreversible inhibitor of factor XIa, with an IC50 of 2.8 nM against human factor XIa. BMS-262084 also inhibits human tryptase (IC50=5 nM). BMS-262084 exhibits antithrombotic effects[1][2].

Name	(2S,3R)-1-[4-(tert-butylcarbamoyl)piperazine-1-carbonyl]-3-[3-(diaminomethylideneamino)propyl]-4-oxoazetidine-2-carboxylic acid
Synonyms	2-Azetidinecarboxylic acid,3-(3-((aminoiminomethyl)amino)propyl)-1-((4-(((1,1-dimethylethyl)amino)carbonyl)-1-piperazinyl)carbonyl)-4-oxo-,(2S,3R)

Description	BMS-262084 is a potent, selective and irreversible inhibitor of factor XIa, with an IC50 of 2.8 nM against human factor XIa. BMS-262084 also inhibits human tryptase (IC50=5 nM). BMS-262084 exhibits antithrombotic effects[1][2].
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> Ser/Thr Protease Research Areas >> Cardiovascular Disease Signaling Pathways >> Metabolic Enzyme/Protease >> Factor Xa
Target	IC50: 2.8 nM (factor XIa), 5 nM (tryptase)[1]
In Vitro	BMS-262084 shows more than 70-fold selectivity for human factor XIa (IC50=2.8 nM) over tryptase, trypsin, urokinase, plasma kallikrein, plasmin, yhrombin (factor IIa) and Factor IXa (IC50=0.005, 0.05, 0.542, 0.55, 1.7,10.5, and 17.4 μM, respectively)[1]. BMS-262084 (1-100 μM) doubles the activated thromboplastin time in human and rat plasma at 0.14 and 2.2 μM, respectively[1].
In Vivo	BMS-262084 (2-12 mg/kg + 2-12 mg/kg/h; i.v.) reduces carotid artery thrombus weight and improves both vessel patency and integrated flow in rats[1]. Animal Model: Male Sprague Dawley rats (310-390 g) were induced venous thrombosis by FeCl2[1] Dosage: 2 mg/kg + 2 mg/kg/h, 6 mg/kg + 6 mg/kg/h, 12 mg/kg + 12 mg/kg/h Administration: I.v. 10 min before FeCl2 application Result: Reduced carotid artery thrombus weight by 73% at the dose of 12 mg/kg + 12 mg/kg/h. Improved both vessel patency and integrated flow.
References	[1]. Schumacher WA, et, al. Antithrombotic and hemostatic effects of a small molecule factor XIa inhibitor in rats. Eur J Pharmacol. 2007 Sep 10;570(1-3):167-74. [2]. Qian X, et, al. A stereoselective synthesis of BMS-262084, an azetidinone-based tryptase inhibitor. J Org Chem. 2002 May 31;67(11):3595-600.

Molecular Formula	C₁₈H₃₁N₇O₅
Molecular Weight	425.48300
Exact Mass	425.23900
PSA	175.65000
LogP	0.61600

Hazard Codes	Xi

253174-92-4	1549811-36-0
1675201-90-7	543730-41-2
1174046-72-0	918348-67-1
1059734-66-5	2691796-83-3
1272353-82-8	290315-45-6