ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate
Pradaxa mesylate
CAS: 872728-81-9
Molecular Formula: C35H45N7O8S
ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate - Names and Identifiers
| Name | Pradaxa mesylate |
| Synonyms | Pradaxa mesylate Dabigatran mesylate Dabigatran etexilate mesylate Dabigatran Mesylate Reference Dabigatran etexilate mesylate,Pradaxa Ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin- ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate (Z)-ethyl 3-(2-(((4-(N'-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate N-[[2-[[[4-[[[(Hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine ethyl ester monomethanesulfonat N-[[2-[[[4-[[[(Hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine ethyl ester monomethanesulfonat supplier in Chin |
| CAS | 872728-81-9 |
| EINECS | 828-727-6 |
ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate - Physico-chemical Properties
| Molecular Formula | C35H45N7O8S |
| Molar Mass | 723.85 |
| Melting Point | >125°C |
| Solubility | DMSO (Slightly, Heated), Methanol (Slightly) |
| Appearance | Solid |
| Color | White to Pale Yellow |
| Storage Condition | Refrigerator |
ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 1.382 ml | 6.908 ml | 13.815 ml |
| 5 mM | 0.276 ml | 1.382 ml | 2.763 ml |
| 10 mM | 0.138 ml | 0.691 ml | 1.382 ml |
| 5 mM | 0.028 ml | 0.138 ml | 0.276 ml |
Last Update：2024-01-02 23:10:35
ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate - Reference Information
| Introduction | dabigatran mesylate is a direct thrombin inhibitor used in clinic, which is a new type of oral anticoagulant. The mechanism of action is to inhibit the formation of thrombus by reversibly and strongly competing for the specific binding site of fibrin to thrombin, so that the formation of fibrin is blocked. |
| mechanism of action | dabigatran mesylate is a prodrug of dabigatran, after metabolism in vivo, it is converted into active dabigatran. Compared with warfarin, dabigatran mesylate does not require frequent monitoring of coagulation function and adjustment of dosage during treatment, and has less drug interaction and is not affected by eating, thereby improving the medication compliance of patients. |
| preparation process | the preparation method of dabigatran mesylate, the operation process is described as follows:(1) 3-[[2-[[(4-amidinophenyl)] amino] methyl]-1-methyl -1H-benzimidazole-5-carbonyl] (pyridin-2-yl) amino]-Propionic Acid Ethyl Ester P-toluenesulfonate and potassium carbonate are added into the dissolving agent and mixed uniformly; specific dosage, 3-[[[2-[(4-amidinophenyl)] amino] methyl]-1-methyl -1H-benzimidazole-5-carbonyl] (pyridin-2-yl) amino] -Ethyl propionate p-toluenesulfonate dosage is 40g, potassium carbonate dosage is 56G; Mixing operation, the dissolving agent is acetone-water system; The acetone-water system, specifically, the solution is prepared by mixing 1000mL of acetone and 550ml of water. The 3-[[2-[[(4-amidinophenyl)] amino] methyl]-1-methyl -1H-benzimidazole-5-carbonyl] (pyridin-2-yl) amino]-Propionic Acid Ethyl Ester P-toluenesulfonate, prepared by the following steps, 3-[[2-[[(4-cyanophenyl)] amino] methyl]-1-methyl -1H-benzimidazol-5-yl] carbonyl] pyridin-2-ylamino] propionic acid ethyl ester, methanol into the reaction kettle; Specific dosage, Methanol 300G, 3-[[2-[(4-cyanophenyl)] amino] methyl]-1-methyl-1h-benzimidazol-5-yl] carbonyl] pyridin-2-ylamino] propionic acid ethyl ester was used in an amount of 50g, that is, the amount of methanol added is 3-[[[2-[(4-cyanophenyl)] 6 times the mass of ethyl amino] methyl]-1-methyl -1H-benzimidazol-5-yl] carbonyl] pyridin-2-ylamino] propanoate; B, hydrogen chloride gas to saturation, reaction at room temperature for 24 hours; C, after vacuum evaporation, add 300g of methanol to dissolve, enter ammonia to saturation, react at room temperature for 24 hours; D, then add P-toluenesulfonic acid, Crystallization was stirred, filtered, washed (washed with acetone) and dried to obtain 3-[[[2-[(4-amidinophenyl)] amino] methyl]-1-methyl -1H-benzimidazole-5-carbonyl] (pyridin-2-yl) amino]-Propionic Acid Ethyl Ester P-toluenesulfonate; Specific dosage, P-toluenesulfonic acid dosage 31G; final preparation of 3-[[2-[(4-amidinophenyl)] amino] methyl]-1-methyl -1H-benzimidazole-5-carbonyl] (pyridin-2-yl) amino]-Propionic Acid Ethyl Ester P-toluenesulfonate 42.0g. (2) Adding N-hexyl chloroformate to the reaction system mixed uniformly in step (1), reacting at room temperature (about 20 ℃) for about 3H; Then crystallizing at about 4 ℃, the crude product was filtered; The amount of N-hexyl chloroformate was 11G corresponding to the amount in step (1). (3) Add 300ml of refined solvent ethanol to the crude product obtained in step (2) and dissolve it at about 60 ° C. After complete dissolution, cool the reaction solution to about 4 ° C. For crystallization, filter it, dabigatran et al 25.0g. (4) The dabigatran etexilate obtained in step (3) was dissolved in 20.0g of reaction solvent acetone (3.2) at about 42 ° C. After complete dissolution, g of methanesulfonic acid was added dropwise, after sufficient reaction, the reaction solution was cooled to about 4 ° C. For crystallization, filtered, and the filter cake was dried for 7-8H to obtain dabigatran methanesulfonate, and a total of 21.4g was obtained. The final calculation and test results show that: 3-[[2-[[(4-amidinophenyl)] the weight yield of amino] methyl]-1-methyl-1h-benzimidazole-5-carbonyl] (pyridin-2-yl) amino]-Propionic Acid Ethyl Ester P-toluenesulfonate was 66.9%; the purity determined by high performance liquid chromatography (HPLC) was 99.8%, and the maximum single impurity was 0.08%. |
| oral anticoagulant drugs | Everyone must know that warfarin is currently the main drug for the prevention of stroke and systemic embolism in patients with atrial fibrillation, warfarin has been considered as the gold standard of antithrombotic therapy in this field. However, in clinical practice, it is found that Warfarin interacts with many drugs and diet, such as quinolone and macrolide antibiotics, and it is often impossible to ensure that the dose is always maintained in the therapeutic window, and increased risk of bleeding. In order to ensure the safety of drug use, routine monitoring of coagulation function and adjustment of drug dosage must be carried out. dabigatran group is another new oral anticoagulant drug approved by the U. S. Food and Drug Administration after warfarin, which is a non-peptide thrombin inhibitor, the anticoagulant effect is exerted by specifically and selectively blocking the activity of thrombin (free or bound). It has the characteristics of oral administration, strong effect, no need for special drug monitoring and little drug interaction. It is a major progress in the field of anticoagulant therapy and the prevention of potentially fatal thrombosis. After oral gastrointestinal absorption, it is converted into dabigatran with direct anticoagulant activity in vivo, which prevents fibrinogen from being cleaved into fibrin by binding to fibrin specific binding site of thrombin, thereby blocking the last step of the blood coagulation cascade network and thrombosis. Dabigatran can also dissociate from the fibrin-thrombin conjugate to exert a reversible anticoagulant effect. at the annual meeting of the European Society of Cardiology, 2009, for the first time, the German company Boehringer Ingelheim has published data from the largest atrial fibrillation outcome clinical trial to date-RE-LY (randomized evaluation of long-term anticoagulation therapy with the novel direct thrombin inhibitor dabigatran etexilate). Results: compared with the well-controlled warfarin group, dabigatran etexilate significantly reduced the risk of stroke and embolic disease (including hemorrhagic stroke) and significantly reduced bleeding (Including fatal bleeding and intracranial hemorrhage) occurs with a significant reduction in blood vessels of Mortality Rate. The results also show that dabigatran etexilate provides an effective and stable anticoagulant effect without routine monitoring of coagulation function and dose adjustment. chemical book JinLin edit |
| Application | dabigatran mesylate is a drug substance used in the blood system; Anticoagulant drug; it can be used to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation. dabigatran is a novel synthetic direct thrombin inhibitor and a prodrug of dabigatran, it is a non-peptide thrombin inhibitor. |
| biological activity | Dabigatran etexilate mesylate (BIBR 1048MS) is an orally active Dabigatran prodrug. Dabigatran etexilate mesylate has an anticoagulant effect and can prevent venous thromboembolism and stroke caused by atrial fibrillation. |
| Animal Model: | Male rats (280-350 g) and rhesus monkeys of either sex (3-8 kg) |
| Dosage: | 10, 20 and 50 mg/kg for rats and 1, 2.5 and 5 mg/kg for monkeys |
| Administration: | Oral |
| Result: | Had dose- and time-dependent anticoagulant effects. |
Last Update：2024-04-10 22:29:15
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ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate methanesulfonate
15690-25-2
15690-25-2