Dabigatran ethyl ester

• CAS: 429658-95-7
• Catalog Number: ACM429658957
• Category: Main Products
• Molecular Weight: 499.56
• Molecular Formula: C₂₇H₂₉N₇O₃
• Synonyms: Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate; N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine ethyl ester; C24; Dabigatran ethyl ester; Dabigatran ethyl AcOH Salt; 3-({2-[(4-CARBAMIMIDOYL-PHENYLAMINO)-METHYL]-3-METHYL-3H-BENZOIMIDAZOLE-5-CARBONYL}-PYRIDIN-2-YL-AMINO)-PROPIONIC ACID ETHYL ESTER
• IUPAC Name: ethyl3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate
• SMILES: CCOC(=O)CCN(C1=CC=CC=N1)C(=O)C2=CC3=C(C=C2)N(C(=N3)CNC4=CC=C(C=C4)C(=N)N)C
• InChI Key: BGLLICFSSKPUMR-UHFFFAOYSA-N
• Boiling Point: 774.5ºC at 760 mmHg
• Exact Mass: 499.23300

Case Study

Identification of the Inhibitory Effects of Dabigatran and Dabigatran Ethyl Ester on NQO2 Target

Michaelis, Simon, et al. Journal of medicinal chemistry 55.8 (2012): 3934-3944.

This case study demonstrated the identification of dabigatran and dabigatran ethyl ester as a high-affinity inhibitor of ribosyldihydronicotinamide dehydrogenase (NQO2) - an unexpected new target revealed through unbiased proteomic profiling of the thrombin inhibitor dabigatran.
Capture Compound Mass Spectrometry (CCMS) identified specific dabigatran binders. Molecular docking predicted binding modes to NQO2, and independent biological assays confirmed target engagement and inhibitory potency for both dabigatran and its ethyl ester prodrug.
Key Findings
· CCMS identified NQO2 as a specific binding partner. Functional assays confirmed both dabigatran and dabigatran ethyl ester inhibit NQO2 activity. Crucially, dabigatran ethyl ester demonstrated significantly stronger NQO2 inhibition than the parent compound, aligning with docking predictions of higher affinity.
· The identification of NQO2 inhibition reveals a novel potential aspect of dabigatran's mechanism. The enhanced affinity of the ethyl ester prodrug towards both thrombin and NQO2 highlights a dual advantage. This work validates a workflow (CCMS + modeling + assays) for mapping drug interactomes and rationally tuning binding properties. The role of NQO2 in detoxification and cell growth modulation warrants further investigation into the biological relevance of this interaction.

Custom Q&A

What is the molecular formula of Dabigatran ethyl ester?

The molecular formula of Dabigatran ethyl ester is C27H29N7O3.

What are the synonyms for Dabigatran ethyl ester?

Some synonyms for Dabigatran ethyl ester include BIBR-951, BIBR0951, and Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate.

What is the CAS number of Dabigatran ethyl ester?

The CAS number of Dabigatran ethyl ester is 429658-95-7.

What is the structure of Dabigatran ethyl ester?

The structure of Dabigatran ethyl ester is a molecular diagram consisting of carbon, hydrogen, nitrogen, and oxygen atoms.

What are some chemical safety considerations for Dabigatran ethyl ester?

The reference does not provide specific chemical safety information for Dabigatran ethyl ester.

Is Dabigatran ethyl ester a commonly used drug?

Dabigatran ethyl ester is not mentioned as a commonly used drug in the reference.

What are some of the other names for Dabigatran ethyl ester?

Some other names for Dabigatran ethyl ester are BIBR-951CL, BIBR-951, and BIBR 951.

What is the chemical formula of Dabigatran ethyl ester?

The chemical formula of Dabigatran ethyl ester is C27H29N7O3.

Is Dabigatran ethyl ester a controlled substance?

The reference does not indicate whether Dabigatran ethyl ester is a controlled substance.

What is the IUPAC name of Dabigatran ethyl ester?

The IUPAC name of Dabigatran ethyl ester is Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate.