CAS 211914-50-0|Dabigatran (ethyl ester hydrochloride)
Introduction：Basic information about CAS 211914-50-0|Dabigatran (ethyl ester hydrochloride), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Dabigatran (ethyl ester hydrochloride) | ||
|---|---|---|---|
| CAS Number | 211914-50-0 | Molecular Weight | 536.025 |
| Density | / | Boiling Point | / |
| Molecular Formula | C27H30ClN7O3 | Melting Point | / |
| MSDS | / | Flash Point | / |
Names
| Name | ethyl 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate,hydrochloride |
|---|---|
| Synonym | More Synonyms |
Dabigatran (ethyl ester hydrochloride) BiologicalActivity
| 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. |
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| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>ThrombinResearch 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. |
Chemical & Physical Properties
| Molecular Formula | C27H30ClN7O3 |
|---|---|
| Molecular Weight | 536.025 |
| Exact Mass | 535.209839 |
| PSA | 139.22000 |
| LogP | 5.13950 |
| InChIKey | FHWBKCGBULSVFO-UHFFFAOYSA-N |
| SMILES | CCOC(=O)CCN(C(=O)c1ccc2c(c1)nc(CNc1ccc(C(=N)N)cc1)n2C)c1ccccn1.Cl |
| Storage condition | 2-8℃ |
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 |
