211914-51-1

Basic information

• Product Name: Dabigatran
• Synonyms: 3-[[2-[[(4-carbaMiMidoylphenyl)aMino]Methyl]-1-Met;BIBR 953(Dabigatran);N-[[2-[[[4-(AMinoiMinoMethyl)phenyl]aMino]Methyl]-1-Methyl-1H-benzo[d]iMidazol-5-yl]carbonyl]-N-pyridin-2-yl-beta-alanine;N-[(2-{[(4-carbaMiMidoylphenyl)aMino]Methyl}-1-Methyl-1HbenziMidazol- 5-yl)carbonyl]-N-pyridin-2-yl-beta-alanine;BIBR 953 (Dabigatran, Pradaxa);3-[[2-[[(4-carbaMiMidoylphenyl)aMino]Methyl]-1-Methyl-benzoiMidazole-5-carbonyl]-pyridin-2-yl-aMino];BIB-953;BIBR 953ZW
• CAS NO: 211914-51-1
• Molecular Formula: C25H25N7O3
• Molecular Weight: 471.51
• Product Categories: Inhibitor;Other APIs;Inhibitors;benzimidazol;Dabigatran impurity;Aromatics;Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 211914-51-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 268-272°C
• Boiling Point: 797.1 °C at 760 mmHg
• Flash Point: 435.9 °C
• Appearance: Tan solid
• Density: 1.38 g/cm³
• Vapor Pressure: 8.45E-27mmHg at 25°C
• Refractive Index: 1.694
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Aqueous Acid
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: Dabigatran(CAS DataBase Reference)
• NIST Chemistry Reference: Dabigatran(211914-51-1)
• EPA Substance Registry System: Dabigatran(211914-51-1)

Safety Data

• Hazardous Substances Data: 211914-51-1(Hazardous Substances Data)

Usage

Chemical Properties

Tan Solid

Uses

Different sources of media describe the Uses of 211914-51-1 differently. You can refer to the following data:
1. BIBR 953 (Dabigatran, Pradaxa) is potent nonpeptide thrombin inhibitor with an IC50 of 9.3 nM
2. Nonpeptide, direct thrombin inhibitor. Antithrombotic.

Definition

ChEBI: An aromatic amide obtained by formal condensation of the carboxy group of 2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazole-5-carboxylic acid with the secondary amoino group of N-pyridin-2-yl-b ta-alanine. The active metabolite of the prodrug dabigatran etexilate, it acts as an anticoagulant which is used for the prevention of stroke and systemic embolism.

Biological Activity

bibr 953 is a potent, reversible, and direct inhibitor of thrombin with ic50 value of 9.3nm [1].bibr 953 shows a favorable selectivity profile and strong activity in vitro with a ki value of 4.5nm. it also exhibits the best activity profile in vivo following administration to rats. bibr 953 is designed to be converted into an orally active prodrug bibr 1048 due to its highly polar, zwitterionic nature and poor oral absorption. bibr 953 inhibits thrombin in a competitive fashion. this inhibition is rapid and reversible. bibr 953 inhibits both clot-bound and free thrombin. bibr 953 is demonstrated to have an anticoagulant efficacy both in vitro and ex vivo. since thrombin can affect cell behavior and response in various tissue types via par signaling, bibr 953 is found to be beneficial in many diseases including inflammation, infection, fibrosis and cancer.

references

[1] hauel nh, nar h, priepke h, ries u, stassen jm, wienen w. structure-based design of novel potent nonpeptide thrombin inhibitors. j med chem. 2002 apr 25;45(9):1757-66.[2] van ryn j, goss a, hauel n, wienen w, priepke h, nar h, clemens a. the discovery of dabigatran etexilate. front pharmacol. 2013 feb 12;4:12.

InChI:InChI=1/C25H25N7O3/c1-31-20-10-7-17(25(35)32(13-11-23(33)34)21-4-2-3-12-28-21)14-19(20)30-22(31)15-29-18-8-5-16(6-9-18)24(26)27/h2-10,12,14,29H,11,13,15H2,1H3,(H3,26,27)(H,33,34)