Dabigatran etexilate (CHEM020679)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 07:19:04 UTC
Update Date2016-11-09 01:16:15 UTC
Accession NumberCHEM020679
Identification
Common NameDabigatran etexilate
ClassSmall Molecule
DescriptionAn aromatic amide obtained by formal condensation of the carboxy group of 2-{carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazole-5-carboxylic acid with the secondary amino group of ethyl N-pyridin-2-yl-beta-alaninate. A prodrug for dabigatran, a thrombin inhibitor and anticoagulant which is used for the prevention of stroke and systemic embolism.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PradaxaKegg
Dabigatran etexilic acidGenerator
DabigatranHMDB
Ethyl 3-[[[4-[[[(hexyloxyl)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino] propanoateHMDB
Etexilate mesylate, dabigatranHMDB
Etexilate, dabigatranHMDB
BIBR 1048HMDB
Mesylate, dabigatran etexilateHMDB
N-((2-(((4-(Aminoiminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)-N-2-pyridinyl-beta-alanineHMDB
Dabigatran etexilate mesylateHMDB
Chemical FormulaC34H41N7O5
Average Molecular Mass627.733 g/mol
Monoisotopic Mass627.317 g/mol
CAS Registry Number211915-06-9
IUPAC Nameethyl 3-(1-{2-[({4-[amino({[(hexyloxy)carbonyl]imino})methyl]phenyl}amino)methyl]-1-methyl-1H-1,3-benzodiazol-5-yl}-N-(pyridin-2-yl)formamido)propanoate
Traditional Namedabigatran etexilate
SMILESCCCCCCOC(=O)N=C(N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C3=CC=CC=N3)N2C)C=C1
InChI IdentifierInChI=1S/C34H41N7O5/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44)
InChI KeyKSGXQBZTULBEEQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Aralkylamine
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Pyridine
  • Benzenoid
  • Imidolactam
  • Azole
  • Imidazole
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Carboxamide group
  • Carbonic acid derivative
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Amidine
  • Carboxylic acid amidine
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Azacycle
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic oxygen compound
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0047 g/LALOGPS
logP5.17ALOGPS
logP4.59ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)17.89ChemAxon
pKa (Strongest Basic)3.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area154.03 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity176.43 m³·mol⁻¹ChemAxon
Polarizability71.11 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001v-3234390000-c2177c303cbef52afbdfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004r-0292116000-55b368cbe92da888e681Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00kk-0981100000-78856b63936cf67ebce2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004r-0292116000-55b368cbe92da888e681Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-4720194000-b25f304a4eefb48ffb14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uds-9634660000-7ac6e0cd9b01e5cd8430Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-4942200000-823214c2258288f41cbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-2200592000-91bb2cde7f5a1c074cffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008d-3500940000-5f6725f159c9fa1d9ac1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-4504930000-e756884bbf82c6cfced2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000019000-b01a3a5bf142faf27699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0001960000-f016ad334f1f10cd9561Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005i-3913404000-8193e59d4a4ff6967cd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000259000-c2af6ee3f89a87dfae64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1000921000-06293e9a87d653604565Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-1001900000-49277b2224b211f8de10Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06695
HMDB IDHMDB0015641
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDabigatran
Chemspider ID4948999
ChEBI ID70746
PubChem Compound ID213023
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21265583
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21429525
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21542663
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21748501
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21859976
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21881389
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22252796
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22276081
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22298812
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22318514
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22348256
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22422743
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22431533
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22488474
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22536678
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22552763
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22563715
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22564134
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22669799
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22782539
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22803489
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22995531
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23476049
24. Eriksson BI, Dahl OE, Buller HR, Hettiarachchi R, Rosencher N, Bravo ML, Ahnfelt L, Piovella F, Stangier J, Kalebo P, Reilly P: A new oral direct thrombin inhibitor, dabigatran etexilate, compared with enoxaparin for prevention of thromboembolic events following total hip or knee replacement: the BISTRO II randomized trial. J Thromb Haemost. 2005 Jan;3(1):103-11.
25. Stangier J, Eriksson BI, Dahl OE, Ahnfelt L, Nehmiz G, Stahle H, Rathgen K, Svard R: Pharmacokinetic profile of the oral direct thrombin inhibitor dabigatran etexilate in healthy volunteers and patients undergoing total hip replacement. J Clin Pharmacol. 2005 May;45(5):555-63.
26. Di Nisio M, Middeldorp S, Buller HR: Direct thrombin inhibitors. N Engl J Med. 2005 Sep 8;353(10):1028-40.
27. Eriksson BI, Dahl OE, Rosencher N, Kurth AA, van Dijk CN, Frostick SP, Kalebo P, Christiansen AV, Hantel S, Hettiarachchi R, Schnee J, Buller HR: Oral dabigatran etexilate vs. subcutaneous enoxaparin for the prevention of venous thromboembolism after total knee replacement: the RE-MODEL randomized trial. J Thromb Haemost. 2007 Nov;5(11):2178-85.
28. Eriksson BI, Dahl OE, Rosencher N, Kurth AA, van Dijk CN, Frostick SP, Prins MH, Hettiarachchi R, Hantel S, Schnee J, Buller HR: Dabigatran etexilate versus enoxaparin for prevention of venous thromboembolism after total hip replacement: a randomised, double-blind, non-inferiority trial. Lancet. 2007 Sep 15;370(9591):949-56.
29. Ezekowitz MD, Reilly PA, Nehmiz G, Simmers TA, Nagarakanti R, Parcham-Azad K, Pedersen KE, Lionetti DA, Stangier J, Wallentin L: Dabigatran with or without concomitant aspirin compared with warfarin alone in patients with nonvalvular atrial fibrillation (PETRO Study). Am J Cardiol. 2007 Nov 1;100(9):1419-26. Epub 2007 Aug 17.
30. Ginsberg JS, Davidson BL, Comp PC, Francis CW, Friedman RJ, Huo MH, Lieberman JR, Muntz JE, Raskob GE, Clements ML, Hantel S, Schnee JM, Caprini JA: Oral thrombin inhibitor dabigatran etexilate vs North American enoxaparin regimen for prevention of venous thromboembolism after knee arthroplasty surgery. J Arthroplasty. 2009 Jan;24(1):1-9. doi: 10.1016/j.arth.2008.01.132. Epub 2008 Apr 14.
31. Wolowacz SE, Roskell NS, Plumb JM, Caprini JA, Eriksson BI: Efficacy and safety of dabigatran etexilate for the prevention of venous thromboembolism following total hip or knee arthroplasty. A meta-analysis. Thromb Haemost. 2009 Jan;101(1):77-85.
32. Connolly SJ, Ezekowitz MD, Yusuf S, Eikelboom J, Oldgren J, Parekh A, Pogue J, Reilly PA, Themeles E, Varrone J, Wang S, Alings M, Xavier D, Zhu J, Diaz R, Lewis BS, Darius H, Diener HC, Joyner CD, Wallentin L: Dabigatran versus warfarin in patients with atrial fibrillation. N Engl J Med. 2009 Sep 17;361(12):1139-51. doi: 10.1056/NEJMoa0905561. Epub 2009 Aug 30.
33. Bauer KA: New oral anticoagulants in development: potential for improved safety profiles. Rev Neurol Dis. 2010;7(1):1-8.
34. Scaglione F: New oral anticoagulants: comparative pharmacology with vitamin K antagonists. Clin Pharmacokinet. 2013 Feb;52(2):69-82. doi: 10.1007/s40262-012-0030-9.
35. European Medicines Agency: http://www.ema.europa.eu/humandocs/PDFs/EPAR/pradaxa/H-829-en6.pdf
36. Abrams P and Marzella N: Dabigatran (Rendix): A Promising New Oral Direct Thrombin Inhibitor. Drug Forecast. 2007;32(5):271-5.: http://www.pharmscope.com/ptjournal/fulltext/32/5/PTJ3205271.pdf