| Identification | Back Directory | [Name]
Dabigatran Etexilate Mesylate | [CAS]
872728-81-9 | [Synonyms]
Dabig
CS-900
Pradaxa
ate MesyL
BIBR 1048MS
atran EtexiL
Pradaxa Mesylate
Dabigatran EtexiL
Dabigatran mesylate
Dabigatran Mesylate Reference
Dabigatran etexilate mesylate
Dabigatran Etexilate Mesylate Pellet
Dabigatran etexilate Methanesulfonate
Dabigatran etexilate mesylate,Pradaxa
Dabigatran Etexilate Mesylate USP/EP/BP
Dabigatran etexilate Mesylate 872728-81-9
PRADAXA; BIBR 1048MS; DABIGATRAN ETEXILATE METHANESULFONATE
Ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-
N-[[2-[[[4-[[[(Hexyloxy)carbonyl]aMino]iMinoMethyl]phenyl]aMino]Methyl]-1-Methyl-1H-benziMidazol-5-y
3-([2-[[(4-(N-n-hexyloxycarbonylcarbamimidoyl)-phenylamino)-methyl]]-1-methyl-1H-benzimidazole-5-carbonyl]-pyridin-2-yl-amino)ethyl propionate mesylate
[[[(Hexyloxy)carbonyl]aMino]iMinoMethyl]phenyl]aMino]Methyl]-1-Methyl-1H-benziMidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanineethylesterMonoMethanesulfonat
Hexyl 2-(4-(((5-((3-ethoxy-3-oxopropyl)(pyridin-2-yl)carbaMoyl)-1-Methyl-1H-benzo[d]iMidazol-2-yl)Methyl)aMino)benzylidene)hydrazinecarboxylate Methanesulfonate
(E)-hexyl 2-(4-((5-((3-ethoxy-3-oxopropyl)(pyridin-2-yl)carbaMoyl)-1-Methyl-1H-benzo[d]iMidazol-2-yl)MethylaMino)benzylidene)hydrazinecarboxylate Methanesulfonate
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-β-alanine Ethyl Ester 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 | [EINECS(EC#)]
828-727-6 | [Molecular Formula]
C34H41N7O5.CH4O3S | [MDL Number]
MFCD17215180 | [MOL File]
872728-81-9.mol | [Molecular Weight]
723.84 |
| Chemical Properties | Back Directory | [Melting point ]
>125°C | [storage temp. ]
Refrigerator | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly) | [form ]
Solid | [color ]
White to Pale Yellow | [InChIKey]
XETBXHPXHHOLOE-UHFFFAOYSA-N | [SMILES]
S(O)(=O)(=O)C.CN1C(=NC2C=C(C(=O)N(C3N=CC=CC=3)CCC(=O)OCC)C=CC1=2)CNC1C=CC(C(=N)NC(=O)OCCCCCC)=CC=1 |
| Hazard Information | Back Directory | [Description]
Dabigatran etexilate mesylate(872728-81-9) is a clinical direct thrombin inhibitor and a new type of oral anticoagulant. It can inhibit the formation of thrombus by reversibly and potently competing with the fibrin-specific binding site of thrombin to block fibrin generation.
| [Chemical Properties]
Off-White to Pale Yellow Solid | [Clinical Use]
Dabigatran Etexilate Mesylate(872728-81-9) is a direct thrombin inhibitor indicated to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation.
| [Uses]
Nonpeptide, direct thrombin inhibitor. Antithrombotic. | [Definition]
ChEBI: A methanesulfonate salt obtained by reaction of dabigatran etexilate with one equivalent of dabigatran etexilate. A prodrug for dabigatran, a thrombin inhibitor and anticoagulant which is used for the prevention of stroke and systemic embolism. | [Brand name]
Pradaxa | [Biological Activity]
Dabigatran etexilate mesylate (BIBR 1048MS) is an orally active prodrug of Dabigatran. Dabigatran etexilate mesylate has anticoagulant properties and can prevent venous thromboembolism and stroke due to atrial fibrillation. | [Mechanism of action]
Dabigatran etexilate mesylate is a prodrug of dabigatran that is metabolized in the body and converted to the active dabigatran. Compared with warfarin, dabigatran etexilate mesylate does not require frequent monitoring of coagulation function and dose adjustment during treatment, and there are fewer interactions between drugs and is not affected by eating, thus improving patients' medication compliance. | [Side effects]
The most common adverse reactions to Dabigatran Etexilate Mesylate(872728-81-9) (150 mg) were bleeding and gastrointestinal events (i.e. dyspepsia, nausea, epigastric pain, gastrointestinal bleeding, and diarrhoea). Very few patients experienced drug hypersensitivity (including urticaria, rash and pruritus), anaphylactic oedema, anaphylactic reactions and anaphylaxis.
| [Synthesis]
Using ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate (52.6 kg, recommended to be pre-purified by recrystallization from ethyl acetate) and methanesulfonic acid as the raw material, the following steps were carried out:
1. add pre-purified ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionate to an inerted stirring apparatus.
2. 293 kg of acetone is added, stirred and heated to 40 °C to 46 °C until a clarified solution is formed.
3. the solution was filtered through a lens filter into a second stirring device and subsequently cooled to 30°C to 36°C.
4. in another vessel, 33 kg of acetone was pre-cooled to 0 °C to 5 °C, 7.9 kg of 99.5% methanesulfonic acid and 9 kg of acetone were added and mixed well.
5. The methanesulfonic acid solution was added stoichiometrically over 15 to 40 minutes to a solution of ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionate in a second apparatus, maintained at a temperature of 26° C. to 36° C. The ethyl 3-(2-(((4-(N-(hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benz[d]imidazole-5-carboxamide)propionate solution was added in a second apparatus, maintained at a temperature of 26° C. to 36° C.
6. After addition, stirring was continued at 26°C to 33°C for 40 to 60 minutes.
7. the mixture was cooled to 17°C to 23°C and stirred for an additional 40 to 80 minutes.
8. The crystal suspension was filtered and washed with a total of 270 L of acetone.
9. The product was dried under vacuum at not more than 50 °C for at least 4 hours.
Yield: 54.5-59.4 kg, based on a theoretical yield of 90%-98% for ethyl 3-(2-(((4-(N-((hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate. | [in vivo]
Dabigatran etexilate mesylate (BIBR 1048MS; oral; 10, 20 and 50 mg/kg for rats and 1, 2.5 and 5 mg/kg for monkeys) has dose- and time-dependent anticoagulant effects and has maximum effects between 30 and 120 min after administration, respectively.Dabigatran etexilate mesylate maximally and significantly prolongs partial thromboplastin time (aPTT) to 25.2, 38.4 and 78.3 s in 30 min after 10, 20 and 50 mg/kg oral doses, respectively.Dabigatran etexilate mesylate maximally prolongs the aPTT to 34.3 s, 44.0 s, and 63.0 s, respectively, 2h after 1, 2.5 or 5 mg/kg doses in the monkey. | [References]
[1] Patent: WO2012/44595, 2012, A1. Location in patent: Page/Page column 15
[2] Patent: WO2014/192030, 2014, A2. Location in patent: Page/Page column 26 |
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