212321-78-3

Basic information

• Product Name: Desethyl Dabigatran Etexilate
• Synonyms: Desethyl Dabigatran Etexilate;Desethyl Pradaxa;N-[[2-[[[4-[[[(Hexyloxy)carbonyl]aMino]iMinoMethyl]phenyl]aMino]Methyl]-1-Methyl-1H-benziMidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine;Dabigatran Etexilate O-Desethyl Impurity;3-[[2-[[4-[(Z)-N'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid;(E)-3-(2-(((4-(N'-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoic acid
• CAS NO: 212321-78-3
• Molecular Formula: C₃₂H₃₇N₇O₅
• Molecular Weight: 599.68008
• Product Categories: Aromatics;Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Nucleotides;Pharmaceuticals;Dabigatran impurity;benzimidazol
• Mol File: 212321-78-3.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Methanol
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: Desethyl Dabigatran Etexilate(CAS DataBase Reference)
• NIST Chemistry Reference: Desethyl Dabigatran Etexilate(212321-78-3)
• EPA Substance Registry System: Desethyl Dabigatran Etexilate(212321-78-3)

Safety Data

• Hazardous Substances Data: 212321-78-3(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

A metabolite of Dabigatran Etexilate (D100150).

Upstream product

• 211915-06-9 dabigatran etexilate 
• 6092-54-2 n-hexyl chloroformate 
• 211915-06-9 dabigatran etexilate 
• 429658-95-7 3-({2-[(4-carbamimidoylphenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid ethyl ester 
• 211915-84-3 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester 
• 42288-26-6 (4-cyanophenyl)glycine 
• 211915-06-9 dabigatran etexilate 
• 948551-71-1 3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate 

Downstream Products

• 1415901-76-6 C₄₀H₄₇N₉O₅ 
• 1408238-37-8 3-(2-(((4-(((hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionic acid 
• 211915-00-3 methyl-3-[[[2-[[[4-[amino[[[(hexyloxy)carbonyl]imino]methyl]]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionate 
• 1419178-59-8 3-({2-[(4-{amino-[(E)-hexyloxycarbonylimino]methyl}phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid {2-methoxy-4-[(E)-2-methoxycarbonylvinyl]phenyl} ester 

Relevant articles and documents

Identification of carboxylesterase-dependent dabigatran etexilate hydrolysis

Dabigatran etexilate (DABE) is an oral prodrug that is rapidly converted to the active thrombin inhibitor, dabigatran (DAB), by serine esterases. The aims of the present study were to investigate the in vitro kinetics and pathway of DABE hydrolysis by human carboxylesterase enzymes, and the effect of alcohol on these transformations. The kinetics of DABE hydrolysis in two human recombinant carboxylesterase enzymes (CES1 and CES2) and in human intestinal microsomes and human liver S9 fractions were determined. The effects of alcohol (a known CES1 inhibitor) on the formation of DABE metabolites in carboxylesterase enzymes and human liver S9 fractions were also examined. The inhibitory effect of bis(4-nitrophenyl) phosphate on the carboxylesterase-mediated metabolism of DABE and the effect of alcohol on the hydrolysis of a classic carboxylesterase substrate (cocaine) were studied to validate the in vitro model. The ethyl ester of DABE was hydrolyzed exclusively by CES1 to M1 (Km 24.9 6 2.9 μM, Vmax 676 6 26 pmol/min per milligram protein) and the carbamate ester of DABE was exclusively hydrolyzed by CES2 to M2 (Km 5.5 6 0.8 μM; Vmax 71.1 6 2.4 pmol/min per milligram protein). Sequential hydrolysis of DABE in human intestinal microsomes followed by hydrolysis in human liver S9 fractions resulted in complete conversion to DAB. These results suggest that after oral administration of DABE to humans, DABE is hydrolyzed by intestinal CES2 to the intermediate M2 metabolite followed by hydrolysis of M2 to DAB in the liver by CES1. Carboxylesterase-mediated hydrolysis of DABE was not inhibited by alcohol. Copyright

PROCESSES FOR THE PREPARATION OF DABIGATRAN ETEXILATE AND INTERMEDIATES THEREOF

The present invention relates to a process for the preparation of dabigatran etexilate of Formula (I), or a pharmaceutically acceptable salt thereof, to processes for the preparation of intermediates of dabigatran etexilate, and to dabigatran etexilate in substantially pure form.