211914-50-0

211914-50-0 structure

Name: Dabigatran (ethyl ester hydrochloride)
Chemical Name: ethyl 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate,hydrochloride
CAS Number: 211914-50-0
Molecular Formula: C₂₇H₃₀ClN₇O₃
Molecular Weight: 536.025
Catalog: Biochemical Amino acids and their derivatives Alanine derivatives
Create Date: 2018-12-05 01:51:34
Modify Date: 2024-01-03 07:42:50
Dabigatran ethyl ester hydrochloride is a potent inhibitor of ribosyldihydronicotinamide dehydrogenase (NQO2) with an IC50 value of 0.8 μM and a thrombin inhibitor.

Name	ethyl 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate,hydrochloride
Synonyms	Ethyl N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-2-pyridinyl-β-alaninate hydrochloride (1:1) β-Alanine, N-[[2-[[[4-(aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-, ethyl ester, hydrochloride (1:1) Dabigatran (ethyl ester hydrochloride) N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride Dabigatran Ethyl Ester Hydrochloride Salt

Description	Dabigatran ethyl ester hydrochloride is a potent inhibitor of ribosyldihydronicotinamide dehydrogenase (NQO2) with an IC50 value of 0.8 μM and a thrombin inhibitor.
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> Thrombin Research Areas >> Cardiovascular Disease
Target	IC50: 0.8 μM (NQO2)[1]
In Vitro	The Ki of dabigatran (ethyl ester hydrochloride) toward NQO2 is 0.9 μM and the IC50 is 0.8 μM. The ethyl ester group of dabigatran (ethyl ester hydrochloride) significantly extends the interaction surface especially with hydrophobic amino acids such as Ile 128 and Met 154. Dabigatran ethyl ester has higher affinity than Dabigatran to both thrombin and NQO2[1]. Dabigatran is a highly selective, reversible, and potent thrombin inhibitor and is orally available as the prodrug, dabigatran etexilate[2].
In Vivo	Dabigatran (Ki=4.5 nM) could bind to human thrombin selectively, and reversibly to realize a strong and long-lasting anticoagulant effect[3].
Kinase Assay	NQO2 (0.5 μM) is incubated with the substrate mitomycin C (50 μM) and four different Dabigatran concentrations in 100 mM potassium phosphate buffer (pH 5.8) at room temperature for 5 min prior to the addition of NADH (in increasing concentrations) as a cosubstrate and photometric monitoring at 340 nm for 30 min at rt. Ki values are determined. Data generated are used to calculate the IC50 of inhibition of NQO2 activity[1].
References	[1]. Michaelis S, et al. Dabigatran and dabigatran ethyl ester: potent inhibitors of ribosyldihydronicotinamide dehydrogenase (NQO2). J Med Chem. 2012 Apr 26;55(8):3934-44. [2]. Eisert WG, et al. Dabigatran: an oral novel potent reversible nonpeptide inhibitor of thrombin. Arterioscler Thromb Vasc Biol. 2010 Oct;30(10):1885-9. [3]. Hauel NH, et al. Structure-based design of novel potent nonpeptide thrombin inhibitors. J Med Chem. 2002 Apr 25;45(9):1757-66.

Molecular Formula	C₂₇H₃₀ClN₇O₃
Molecular Weight	536.025
Exact Mass	535.209839
PSA	139.22000
LogP	5.13950
Storage condition	2-8℃

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