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Dabigatran Etexilate

PubChem CID
135565674
Structure
Dabigatran Etexilate_small.png
Molecular Formula
Synonyms
  • Dabigatran etexilate
  • 211915-06-9
  • Prazaxa
  • Pradax
  • BIBR 1048
Molecular Weight
627.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2019-01-15
  • Modify:
    2025-01-25
Description
Dabigatran etexilate is an oral prodrug that is hydrolyzed to the competitive and reversible direct thrombin inhibitor [dabigatran]. Dabigatran etexilate may be used to decrease the risk of venous thromboembolic events in patients in whom anticoagulation therapy is indicated. In contrast to warfarin, because its anticoagulant effects are predictable, lab monitoring is not necessary. Dabigatran etexilate was approved by the FDA in 2010.
A THROMBIN inhibitor which acts by binding and blocking thrombogenic activity and the prevention of thrombus formation. It is used to reduce the risk of stroke and systemic EMBOLISM in patients with nonvalvular atrial fibrillation.
See also: Dabigatran (has active moiety); Dabigatran Etexilate Mesylate (has salt form).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dabigatran Etexilate.png

1.2 3D Status

Conformer generation is disallowed since too flexible

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl 3-[[2-[[4-(N-hexoxycarbonylcarbamimidoyl)anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=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)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KSGXQBZTULBEEQ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCOC(=O)NC(=N)C1=CC=C(C=C1)NCC2=NC3=C(N2C)C=CC(=C3)C(=O)N(CCC(=O)OCC)C4=CC=CC=N4
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C34H41N7O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 DrugBank ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 Metabolomics Workbench ID

2.3.8 NCI Thesaurus Code

2.3.9 Pharos Ligand ID

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • BIBR 1048
  • dabigatran
  • dabigatran etexilate
  • dabigatran etexilate mesylate
  • Etexilate Mesylate, Dabigatran
  • Etexilate, Dabigatran
  • Mesylate, Dabigatran Etexilate
  • N-((2-(((4-(aminoiminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)-N-2-pyridinyl-beta-alanine
  • Pradaxa

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
627.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
18
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
627.31691743 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
627.31691743 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
152 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
46
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
991
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

132
180 °C

3.2.3 Solubility

1.8mg/ml, partly soluble
MSDS

3.2.4 LogP

3.8
Apotex Inc. Product Monograph: Dabigatran Etexilate
3.8

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> unsed in Switzerland 2014-2016
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 3
View All
Spectra ID
Instrument Type
LC-ESI-qTof
Ionization Mode
Positive
Top 5 Peaks

628.324646 21288

289.10733 20280

273.158752 9212

629.326416 7688

290.110931 5768

Thumbnail
Thumbnail
Notes
From GNPS Library
2 of 3
View All
Spectra ID
Ionization Mode
positive
Top 5 Peaks

289.108154 100

195.112625 73.81

217.612762 73

145.057159 67.42

434.219177 48.17

Thumbnail
Thumbnail
Notes
instrument=qTof

4.1.2 LC-MS

1 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+2H]+
Precursor m/z
314.666
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

289.108154 100

195.112625 73.81

217.612762 73

145.057159 67.42

434.219177 48.17

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
628.324
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

628.324646 100

289.107330 95.26

273.158752 43.27

629.326416 36.11

290.110931 27.10

Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Dabigatran etexilate is available in both oral pellet and capsule form. Dabigatran etexilate pellets are indicated for the treatment of venous thromboembolic events (VTE) in pediatric patients between three months and 12 years of age who have been treated with a parenteral anticoagulant for at least 5 days. They are also indicated in the same age group to reduce the risk of recurrence of VTE in patients who have been previously treated. In capsule form, dabigatran etexilate is indicated in adults to reduce the risk of stroke and systemic embolism associated with non-valvular atrial fibrillation and for the treatment of deep venous thrombosis (DVT) and pulmonary embolism (PE) in patients who have been treated with a parenteral anticoagulant for 5-10 days. It is also indicated in adults to reduce the risk of recurrence of DVT and PE in patients who have been previously treated and for the prophylaxis of DVT and PE in patients who have undergone hip replacement surgery. Lastly, it is indicated in pediatric patients between eight and 18 years of age for the treatment of venous thromboembolic events (VTE) in patients who have been treated with a parenteral anticoagulant for at least 5 days and to reduce the risk of recurrence of VTE in patients who have been previously treated. Dabigatran etexilate is also approved by the EMA to prevent VTE in adult patients. For pediatric patients, Dabigatran etexilate is used to treat TVE and prevent recurrent TVE for patients from birth to less than 18 years of age.

7.2 FDA National Drug Code Directory

7.3 Drug Labels

Drug and label

7.4 Clinical Trials

7.4.1 ClinicalTrials.gov

7.4.2 EU Clinical Trials Register

7.4.3 NIPH Clinical Trials Search of Japan

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Dabigatran etexilate is a double prodrug that is hydrolyzed to the active [dabigatran] by intestinal and hepatic carboxylesterases. Dabigatran is a reversible competitive thrombin inhibitor that directly inhibits the conversion by thrombin of fibrinogen to fibrin, impairing the clotting process and acting as an anticoagulant. Dabigatran use prolongs coagulation markers such as the activated partial thromboplastin time (aPTT), ecarin clotting time (ECT), thrombin time (TT), and dilute thrombin time (dTT), but not the international normalized ratio (INR), which cannot be used in this context as it can in [warfarin] monitoring. As with all anticoagulant therapies, dabigatran carries a risk of bleeding, which may increase with concomitant use of antiplatelet agents, fibrinolytic therapy, heparins, or chronic NSAID use, and should be monitored for. Premature discontinuation of dabigatran, in the absence of an alternative anticoagulant, also carries an increased risk of thromboembolic events. Due to the risk of an epidural or spinal hematoma, dabigatran should generally not be used in the context of neuraxial anesthesia or spinal puncture; if such use is unavoidable, careful monitoring should be employed. Dabigatran should not be used in patients with prosthetic heart valves due to an increased occurrence of major bleeding and thromboembolic events. Dabigatran is a substrate of the P-gp transporter and should generally not be administered together with P-gp inhibitors or inducers, especially in patients with impaired renal function. Lastly, dabigatran or any other direct-acting oral anticoagulant should not be administered in patients with triple-positive antiphospholipid syndrome (APS) due to an increased risk of recurrent thrombotic events. In case of the need for emergency reversal, [idarucizumab] is available for use in adult patients; the safety and efficacy of [idarucizumab] has not been established in pediatric patients yet, for whom reversal may be achieved through hemodialysis, prothrombin complex concentrates, or recombinant FVIIa. However, none of these have been sufficiently evaluated in clinical trials.

8.2 MeSH Pharmacological Classification

Antithrombins
Endogenous factors and drugs that directly inhibit the action of THROMBIN, usually by blocking its enzymatic activity. They are distinguished from INDIRECT THROMBIN INHIBITORS, such as HEPARIN, which act by enhancing the inhibitory effects of antithrombins. (See all compounds classified as Antithrombins.)

8.3 FDA Pharmacological Classification

Non-Proprietary Name
DABIGATRAN ETEXILATE
Pharmacological Classes
Direct Thrombin Inhibitor [EPC]; Thrombin Inhibitors [MoA]

8.4 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AE - Direct thrombin inhibitors

B01AE07 - Dabigatran etexilate

8.5 Absorption, Distribution and Excretion

Absorption
Oral dabigatran has a bioavailability of 3-7%, although the relative bioavailability of dabigatran pellets is 37% higher than that for capsules and the bioavailability increases to 75% when the capsule shell is removed; dabigatran capsules should not be tampered with in any way prior to administration. The Cmax is achieved by one hour following oral dosing, which is extended to two hours if accompanied by a high-fat meal. Dabigatran can be taken with or without food. Dabigatran pharmacokinetics are approximately linear over a range of 10-400 mg in healthy adults and adult patients and it has an accumulation factor of two in adult and pediatric patients.
Route of Elimination
Dabigatran is primarily eliminated in the urine. Following oral administration of radiolabeled dabigatran, 7% of the radioactivity is recovered in urine and 86% is recovered in feces.
Volume of Distribution
Dabigatran has a volume of distribution of 50-70L.
Clearance
Following intravenous administration, renal clearance constitutes ~80% of total dabigatran clearance.

8.6 Metabolism / Metabolites

Dabigatran is administered as the orally available prodrug dabigatran etexilate that is subsequently metabolized to the active form. _In vitro_ studies and observations regarding the oral bioavailability and levels of plasma prodrug suggest extensive first-pass metabolism by carboxylesterases, first by intestinal CES2 to form BIBR0951 (also known as M2) and then subsequently by hepatic CES1 to form [dabigatran]. Dabigatran etexilate can also first undergo CES1-mediated hydrolysis to BIBR1087 (M1) followed by CES2-mediated hydrolysis to [dabigatran], though it is hypothesized that the former pathway accounts for most of the active form in plasma. Dabigatran can undergo 1-_O_-acyl glucuronidation by UGT1A9, UGT2B7, and UGT2B15 followed by acyl migration to form the corresponding 2-_O_-, 3-_O_-, and 4-_O_-acyl glucuronides; all of these acyl glucuronides exhibit activity similar to [dabigatran] but account for a small fraction of recovered metabolites. In addition to these better characterized metabolic pathways, detailed LC/MS characterization suggests a wide variety of possible metabolites following oral or intravenous administration, most of which are present in only trace amounts in plasma, urine, or feces. These include a variety of oxidation, hydrolysis, and conjugation products, including through the addition of mannitol.

8.7 Biological Half-Life

Dabigatran has a half-life of 12-17 hours in adult patients and 12-14 hours in pediatric patients.

8.8 Mechanism of Action

Hemostasis is a complex process that balances coagulation to prevent excessive thrombus formation or excessive bleeding. Central to the coagulation process is the serine protease thrombin (FIIa), which is synthesized as inactive prothrombin (FII) and subsequently activated by FXa/FVa, leading to a positive feedback loop and the production of large quantities of thrombin; once enough thrombin is formed, it cleaves soluble fibrinogen to form insoluble fibrin fibres that, together with aggregated platelets, form a clot. Although beneficial in wound healing, aberrant thrombus formation can lead to serious health consequences. Dabigatran is a univalent reversible direct thrombin inhibitor (DTI) that competitively inhibits thrombin with a Ki of 4.5 ± 0.2 nmol/L. Furthermore, the reversible nature of the inhibition is believed to allow for some normal physiological thrombin function, which may help alleviate some adverse effects associated with anticoagulation therapy. In addition, dabigatran has several glucuronidated metabolites, all of which have been shown to possess _in vitro_ activity similar to the parent compound. In addition to a direct effect on thrombin activity, dabigatran has also been shown to inhibit platelet aggregation, another step in the coagulation pathway. However, the mechanism remains unclear as dabigatran inhibits platelet aggregation stimulated by thrombin and von Willebrand factor (vWF), but not by other pathways such as ADP- or thromboxane A2-induced aggregation.

8.9 Human Metabolite Information

8.9.1 Cellular Locations

  • Extracellular
  • Membrane

9 Use and Manufacturing

9.1 Uses

Use (kg; approx.) in Germany (2009): >50

Consumption (g per capita; approx.) in Germany (2009): 0.000611

Calculated removal (%): 95.4

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 85.7% (6 of 7) of all reports. Pictograms displayed are for 14.3% (1 of 7) of reports that indicate hazard statements.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (14.3%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (14.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (14.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 7 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 6 of 7 reports by companies. For more detailed information, please visit ECHA C&L website.

There is 1 notification provided by 1 of 7 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (14.3%)

Eye Irrit. 2A (14.3%)

STOT SE 3 (14.3%)

10.2 Regulatory Information

REACH Registered Substance

11 Toxicity

11.1 Toxicological Information

11.1.1 Protein Binding

Dabigatran is ~35% bound to plasma proteins, including human serum albumin.

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Chemical Co-Occurrences in Literature

13.4 Chemical-Gene Co-Occurrences in Literature

13.5 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

15.2 Drug-Drug Interactions

15.3 Drug-Food Interactions

  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
  • Avoid St. John's Wort. This herb induces PGP which may reduce the serum levels of dabigatran.
  • Take with a full glass of water.
  • Take with or without food.

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 WHO ATC Classification System

17.4 ChemIDplus

17.5 UN GHS Classification

17.6 NORMAN Suspect List Exchange Classification

17.7 EPA DSSTox Classification

18 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
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  3. DrugBank
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  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
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    https://echa.europa.eu/web/guest/legal-notice
    ß-Alanin,N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-ethylester
    https://chem.echa.europa.eu/100.126.485
    ß-Alanin,N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-ethylester (EC: 606-722-8)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/100550
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  8. ClinicalTrials.gov
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  9. Crystallography Open Database (COD)
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    https://creativecommons.org/publicdomain/zero/1.0/
  10. DailyMed
  11. EU Clinical Trials Register
  12. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  13. Metabolomics Workbench
  14. National Drug Code (NDC) Directory
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  15. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  16. NIPH Clinical Trials Search of Japan
  17. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    DABIGATRAN ETEXILATE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  18. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  19. Pharos
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    https://pharos.nih.gov/about
  20. Therapeutic Target Database (TTD)
  21. Wikidata
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  23. PubChem
  24. GHS Classification (UNECE)
  25. PATENTSCOPE (WIPO)
CONTENTS