Production Method 1

916327-75-8

75-75-2

211915-06-9

75-75-2

Reaction Conditions

1.1 Solvents: 2-Methyltetrahydrofuran ;  60 min, 25 °C; 1 h, 25 °C

Reference

Process for the preparation of ethyl 3-{[(2-{[(4-{N'-[(hexyloxy)carbonyl]carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](2-pyridinyl)amino}propanoate mesylate

Anonymous, IP.com Journal, 2011, 11,

Production Method 2

916327-75-8

75-75-2

211915-06-9

75-75-2

Reaction Conditions

1.1 Solvents: 1-Butanol ;  rt → 50 °C; 1.5 h, 50 °C; 2.5 h, 50 °C → 20 °C; 30 min, 20 °C

Reference

Process For The Preparation of Ethyl 3-[[(2-[[(4-[N'-[(hexyloxy)carbonyl]carbamimidoyl]phenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl)carbonyl](2-pyridinyl)amino]propanoate mesylate

Anonymous, IP.com Journal, 2012, 12,

Production Method 3

211915-06-9

75-75-2

211915-06-9

75-75-2

Reaction Conditions

1.1 Solvents: Acetone ,  Ethyl acetate ;  rt; 2 h, rt

Reference

An improved process for the preparation of Dabigatran Etexilate mesylate and synthesis of its impurities

Devarasetty, Sitaramaiah; et al, Pharma Chemica, 2018, 10(4), 127-148

Production Method 4

211915-06-9

211915-06-9

75-75-2

Reaction Conditions

1.1 Reagents: Methanesulfonic acid Solvents: Acetone ;  rt; 1 h, rt

Reference

Synthesis of dabigatran etexilate mesylate

Cheng, Qingfang; et al, Zhongguo Xinyao Zazhi, 2012, 21(1), 88-91

Production Method 5

1015167-27-7

1449760-91-1

75-75-2

6092-54-2

211915-06-9

75-75-2

Reaction Conditions

1.1 Solvents: Acetone ;  rt → 5 °C
1.2 5 °C → rt; 1 h, rt; cooled; 35 - 40 °C
1.3 Solvents: Acetone ;  20 min, 35 - 40 °C

Reference

Preparation of solid forms of Dabigatran etexilate and Dabigatran etexilate mesylate

Anonymous, IP.com Journal, 2012, 12,

Production Method 6

104-15-4

429658-95-7

75-75-2

6092-54-2

211915-06-9

75-75-2

Reaction Conditions

Reference

Identification, Synthesis, and Strategy for the Reduction of Potential Impurities Observed in Dabigatran Etexilate Mesylate Processes

Zheng, Yong-Yong; et al, Organic Process Research & Development, 2014, 18(6), 744-750

Production Method 7

104-15-4

211915-84-3

211915-06-9

75-75-2

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol
1.2 Reagents: Ammonium hydroxide Solvents: Water
2.1 -
2.2 -

Reference

Identification, Synthesis, and Strategy for the Reduction of Potential Impurities Observed in Dabigatran Etexilate Mesylate Processes

Zheng, Yong-Yong; et al, Organic Process Research & Development, 2014, 18(6), 744-750

Production Method 8

429658-95-7

530-62-1

111-27-3

211915-06-9

75-75-2

Reaction Conditions

1.1 Solvents: Dichloromethane ;  45 - 60 min, 20 - 25 °C; 2 - 3 h, 20 - 25 °C
1.2 Reagents: Potassium carbonate Solvents: Acetonitrile ,  Water ;  10 - 15 min, 30 - 35 °C; 1 - 2 h, 35 °C → 45 °C
2.1 Solvents: Ethanol ,  Ethyl acetate ;  3 - 4 h, 25 - 30 °C

Reference

An improved process for preparation of dabigatran etexilate mesylate

Sharif, S. D. Khasim; et al, Asian Journal of Chemistry, 2017, 29(6), 1253-1257

Dabigatran etexilate Raw materials

• 4-methylbenzene-1-sulfonic acid
• Dabigatran etexilate
• Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate
• Dabigatran Etexilate Tetrahydrate
• Dabigatran Impurity 148
• N,N'-Carbonyldiimidazole
• β-Alanine, N-2-pyridinyl-, ethyl ester, hydrochloride (1:1)
• Methanesulfonic acid
• Hexyl chloroformate
• 1-Hexanol
• Deacetamidine Cyano Dabigatran Ethyl Ester

Dabigatran etexilate Preparation Products

• Dabigatran etexilate (211915-06-9)
• Methanesulfonic acid (75-75-2)

• 1. A comparative study of the molecular structure, lipophilicity, solubility, acidity, absorption and polar surface area of coumarinic anticoagulants and direct thrombin inhibitors
  Milan Remko,Ria Broer,Anna Remková RSC Adv. 2014 4 8072
• 2. A comparative study on the analytical performance of a charged aerosol detector and an ultraviolet detector for the RP-LC analysis of dabigatran etexilate in capsules
  Raquel M. Bernardi,Felipe B. D'Avila,Vítor Todeschini,Pedro E. Fr?ehlich,Ana M. Bergold Anal. Methods 2013 5 4777
• 3. Identification of dabigatran etexilate major degradation pathways by liquid chromatography coupled to multi stage high-resolution mass spectrometry
  Fatma Amrani,Philippe-Henri Secrétan,Hassane Sadou-Yayé,Caroline Aymes-Chodur,Mélisande Bernard,Audrey Solgadi,Najet Yagoubi,Bernard Do RSC Adv. 2015 5 45068
• 4. Design, synthesis, biological evaluation and molecular docking of novel dabigatran derivatives as potential thrombin inhibitors
  Chun-Lei Li,Ming-Hui Dong,Yu-Jie Ren,Li-Hua Li RSC Adv. 2015 5 23737
• 5. Discovery of AZD8165 – a clinical candidate from a novel series of neutral thrombin inhibitors
  K. Abrahamsson,P. Andersson,J. Bergman,U. Bredberg,J. Br?nalt,A.-C. Egnell,U. Eriksson,D. Gustafsson,K.-J. Hoffman,S. Nielsen,I. Nilsson,S. Pehrsson,M. O. Polla,T. Skjaeret,M. Strimfors,C. Wern,M. ?lweg?rd-Halvarsson,Y. ?rtengren Med. Chem. Commun. 2016 7 272

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzimidazoles Benzimidazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzimidazoles

Dabigatran etexilate (CAS No. 211915-06-9): A Comprehensive Overview in Modern Pharmaceutical Research

Dabigatran etexilate, a compound with the chemical identifier CAS No. 211915-06-9, represents a significant advancement in the field of anticoagulant therapy. As a direct oral anticoagulant (DOAC), it has garnered substantial attention for its efficacy and safety profile, particularly in the prevention of thromboembolic events. This introduction aims to provide an in-depth exploration of Dabigatran etexilate, encompassing its pharmacological mechanisms, clinical applications, and the latest research findings that underscore its importance in contemporary medicine.

The pharmacological action of Dabigatran etexilate is primarily attributed to its inhibition of thrombin, a serine protease essential for the formation of fibrin clots. Unlike traditional anticoagulants such as warfarin, which require routine monitoring due to their interaction with vitamin K-dependent clotting factors, Dabigatran etexilate operates through a more targeted mechanism. This specificity not only enhances its therapeutic efficacy but also minimizes the risk of bleeding complications, making it a preferred choice for many patients.

In recent years, numerous clinical trials have demonstrated the superiority of Dabigatran etexilate over conventional anticoagulants in various indications. For instance, studies have shown that it significantly reduces the risk of stroke and systemic embolism in patients with non-valvular atrial fibrillation (NVAF). The once-daily dosing regimen further enhances patient compliance, a critical factor in long-term therapeutic management.

The molecular structure of Dabigatran etexilate, characterized by its carboxylate and ethyl ester groups, contributes to its high bioavailability and rapid absorption after oral administration. This structural feature allows for predictable pharmacokinetic profiles, which are essential for consistent therapeutic outcomes. Additionally, the compound's stability under various physiological conditions ensures prolonged activity, reducing the need for frequent dosing adjustments.

One of the most compelling aspects of Dabigatran etexilate is its extensive research into potential off-label applications. Emerging studies suggest that it may have therapeutic benefits in conditions beyond its primary indication. For example, preliminary research has explored its potential role in reducing inflammation and improving outcomes in patients with acute coronary syndromes. These findings highlight the compound's versatility and open new avenues for further investigation.

The development of Dabigatran etexilate also exemplifies the growing trend towards personalized medicine. By leveraging advanced computational modeling and high-throughput screening techniques, researchers have been able to optimize its molecular structure for enhanced efficacy and reduced side effects. This approach aligns with the broader goal of tailoring therapeutic strategies to individual patient needs, thereby improving overall treatment outcomes.

Furthermore, the safety profile of Dabigatran etexilate has been extensively evaluated through rigorous clinical trials and post-marketing surveillance. These studies have consistently shown that it is well-tolerated across diverse patient populations, including elderly individuals and those with comorbidities. The absence of significant interactions with other commonly prescribed medications further underscores its clinical utility.

Recent advancements in pharmacogenomics have also shed light on genetic factors that influence Dabigatran etexilate's response among patients. By identifying specific genetic markers associated with variations in drug metabolism and efficacy, clinicians can better predict individual responses to therapy. This personalized approach not only enhances treatment effectiveness but also minimizes adverse effects.

The regulatory landscape for Dabigatran etexilate reflects its growing acceptance in global healthcare systems. Regulatory agencies such as the U.S. Food and Drug Administration (FDA) and the European Medicines Agency (EMA) have approved it for use in multiple indications based on robust clinical evidence. These approvals underscore the compound's validity and reliability as a therapeutic option.

As research continues to evolve, new insights into Dabigatran etexilate's mechanisms of action are being uncovered. For instance, studies have explored its interactions with platelets and other components of the coagulation cascade beyond thrombin inhibition. These findings contribute to a more comprehensive understanding of its therapeutic effects and may inform future drug development strategies.

The integration of digital health technologies has also transformed how Dabigatran etexilate is administered and monitored. Mobile applications and wearable devices enable patients to track their medication adherence and detect potential adverse events in real-time. This technology-driven approach enhances patient engagement and improves long-term treatment outcomes.

In conclusion, Dabigatran etexilate (CAS No. 211915-06-9) stands as a cornerstone in modern anticoagulant therapy due to its targeted mechanism of action, favorable safety profile, and broad clinical applications. The latest research findings continue to reinforce its importance in managing thromboembolic disorders while opening new possibilities for expanded use cases. As pharmaceutical science advances, Dabigatran etexilate will undoubtedly remain at the forefront of therapeutic innovation.

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