Dabigatran etexilate

Identification

Summary

Dabigatran etexilate is an anticoagulant used for the prevention of venous thromboembolic events or stroke in patients with recent elective hip or knee replacement surgery and atrial fibrillation.

Brand Names

Pradaxa

Generic Name

Dabigatran etexilate

DrugBank Accession Number

DB06695

Background

Dabigatran etexilate is an oral prodrug that is hydrolyzed to the competitive and reversible direct thrombin inhibitor dabigatran.^5,16,18,19 Dabigatran etexilate may be used to decrease the risk of venous thromboembolic events in patients in whom anticoagulation therapy is indicated.⁵ In contrast to warfarin, because its anticoagulant effects are predictable, lab monitoring is not necessary.⁵ Dabigatran etexilate was approved by the FDA in 2010.¹⁷

Type

Small Molecule

Groups

Approved

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Dabigatran etexilate (DB06695)

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Weight

Average: 627.7332
Monoisotopic: 627.316917457

Chemical Formula

C₃₄H₄₁N₇O₅

Synonyms

• Dabigatran etexilate

External IDs

• BIBR 1048
• BIBR 1048 BS RS1
• BIBR-1048
• BIBR-1048-BS-RS1

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Pharmacology

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.¹⁸

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.¹⁹

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.²⁰

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Deep vein thrombosis		••••••••••••	•••••		•••••••
Prophylaxis of	Deep vein thrombosis		••••••••••••	•••••	••• ••••••••••• •••••••	•••••••
Prevention of	Deep vein thrombosis		••••••••••••	•••••	•••••••••• •••••••	•••••••
Prophylaxis of	Deep venous thrombosis		••••••••••••			•••••••
Treatment of	Pulmonary embolism		••••••••••••	•••••		•••••••

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Dabigatran etexilate is a double prodrug that is hydrolyzed to the active dabigatran by intestinal and hepatic carboxylesterases.^12,13,14 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.^4,7,8,18,19 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.^18,19

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.^18,19

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.⁶

Dabigatran is a univalent reversible direct thrombin inhibitor (DTI) that competitively inhibits thrombin with a K_i of 4.5 ± 0.2 nmol/L.^7,8,18,19 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.⁹ In addition, dabigatran has several glucuronidated metabolites, all of which have been shown to possess in vitro activity similar to the parent compound.⁴

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.^{8,10,11,18,19}

Target	Actions	Organism
AProthrombin	inhibitor	Humans

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 C_max 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.^18,19

Volume of distribution

Dabigatran has a volume of distribution of 50-70L.^18,19

Protein binding

Dabigatran is ~35% bound to plasma proteins, including human serum albumin.^15,18,19

Metabolism

Dabigatran is administered as the orally available prodrug dabigatran etexilate that is subsequently metabolized to the active form.^12,18,19 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.^13,14 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.^12,4,18,19

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.¹²

Hover over products below to view reaction partners

• Dabigatran etexilate
  • BIBR0951/M2
    • Dabigatran
      • Dabigatran 1-O-acylglucuronide metabolite
        • Dabigatran M636
        • Dabigatran M486-2
        • Dabigatran M690
        • Dabigatran 4-O-acylglucuronide metabolite
        • Dabigatran 3-O-acylglucuronide metabolite
        • Dabigatran 2-O-acylglucuronide metabolite
      • Dabigatran M355
        • Dabigatran M354
          • Dabigatran M396
        • Dabigatran M369
          • Dabigatran M325
      • Dabigatran M486
        • Dabigatran M369
          • Dabigatran M325
      • BIBR1151/M324
        • Dabigatran M500
      • Dabigatran M400
  • BIBR1087/M1
    • Dabigatran M630
      • Dabigatran M602
        • Dabigatran M574
    • Dabigatran

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.^18,19

Half-life

Dabigatran has a half-life of 12-17 hours in adult patients and 12-14 hours in pediatric patients.^18,19

Clearance

Following intravenous administration, renal clearance constitutes ~80% of total dabigatran clearance.^18,19

Adverse Effects

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Toxicity

No human studies involving pregnancy, labor and delivery, nursing, or pediatrics^Label. Geriatric patients are at higher risk of adverse effects than younger patients but the risk to benefit ratio is generally still favourable for older patients^Label. Patients with a creatinine clearance of 15-30mL/min should have their doses of dabigatran etexilate reduced, and no data is available for patients with a creatinine clearance below 15mL/min^Label.

In animal studies, dabigatran increases the rates of dead offspring and causes uterine and vaginal bleeding close to birth^Label. Dabigatran may or may not be excreted in breast milk so the risk and benefit of stopping the drug or stopping breast feeding must be considered^Label.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Dabigatran etexilate which could result in a higher serum level.
Abciximab	Dabigatran etexilate may increase the anticoagulant activities of Abciximab.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Dabigatran etexilate.
Abrocitinib	The serum concentration of Dabigatran etexilate can be increased when it is combined with Abrocitinib.
Aceclofenac	The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Dabigatran etexilate.

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.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dabigatran etexilate mesilate	SC7NUW5IIT	872728-81-9	XETBXHPXHHOLOE-UHFFFAOYSA-N

Active Moieties

Name	Kind	UNII	CAS	InChI Key
Dabigatran	prodrug	I0VM4M70GC	211914-51-1	YBSJFWOBGCMAKL-UHFFFAOYSA-N

International/Other Brands

Pradax (Boehringer Ingelheim) / Rendix

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dabigatran Etexilate Accord	Capsule	150 mg	Oral	Accord Healthcare S.L.U.	2023-06-20	Not applicable
Dabigatran Etexilate Accord	Capsule	75 mg	Oral	Accord Healthcare S.L.U.	2023-06-20	Not applicable
Dabigatran Etexilate Accord	Capsule	110 mg	Oral	Accord Healthcare S.L.U.	2023-06-20	Not applicable
Dabigatran Etexilate Accord	Capsule	75 mg	Oral	Accord Healthcare S.L.U.	2023-06-20	Not applicable
Dabigatran Etexilate Accord	Capsule	110 mg	Oral	Accord Healthcare S.L.U.	2023-06-20	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo-dabigatran	Capsule	75 mg	Oral	Apotex Corporation	2019-08-14	Not applicable
Apo-dabigatran	Capsule	110 mg	Oral	Apotex Corporation	2019-02-04	Not applicable
Apo-dabigatran	Capsule	150 mg	Oral	Apotex Corporation	2019-02-04	Not applicable
Dabigatran Etexilate	Capsule	75 mg/1	Oral	Apotex Corp.	2024-02-13	Not applicable
Dabigatran Etexilate	Capsule	150 mg/1	Oral	Camber Pharmaceuticals, Inc.	2020-05-06	Not applicable

Categories

ATC Codes

B01AE07 — Dabigatran etexilate

• B01AE — Direct thrombin inhibitors
• B01A — ANTITHROMBOTIC AGENTS
• B01 — ANTITHROMBOTIC AGENTS
• B — BLOOD AND BLOOD FORMING ORGANS

Drug Categories

• Anticoagulants
• Antithrombins
• Benzimidazoles
• Blood and Blood Forming Organs
• Drugs that are Mainly Renally Excreted
• Enzyme Inhibitors
• Hematologic Agents
• Heterocyclic Compounds, Fused-Ring
• P-glycoprotein substrates
• Protease Inhibitors
• Pyridines
• Serine Protease Inhibitors
• UGT1A9 Substrates
• UGT2B7 substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound 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).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Not Available

Direct Parent

Benzimidazoles

Alternative Parents

Phenylalkylamines / Aniline and substituted anilines / Secondary alkylarylamines / Pyridines and derivatives / N-substituted imidazoles / Imidolactams / Tertiary carboxylic acid amides / Heteroaromatic compounds / Amino acids and derivatives / Carboxylic acid esters / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Carboxamidines / Carboximidamides / Monocarboxylic acids and derivatives / Carbonyl compounds / Organic oxides / Organopnictogen compounds / Hydrocarbon derivatives

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Substituents

Amidine / Amine / Amino acid or derivatives / Aniline or substituted anilines / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Carbonic acid derivative / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid amidine / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidolactam / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / N-substituted imidazole / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenylalkylamine / Propargyl-type 1,3-dipolar organic compound / Pyridine / Secondary aliphatic/aromatic amine / Secondary amine / Tertiary carboxylic acid amide

show 27 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxylic ester, carboxamidine, beta-alanine derivative, pyridines, aromatic amide, benzimidazoles (CHEBI:70746)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

2E18WX195X

CAS number

211915-06-9

InChI Key

KSGXQBZTULBEEQ-UHFFFAOYSA-N

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)

IUPAC Name

ethyl 3-(1-{2-[({4-[(1E)-amino({[(hexyloxy)carbonyl]imino})methyl]phenyl}amino)methyl]-1-methyl-1H-1,3-benzodiazol-5-yl}-N-(pyridin-2-yl)formamido)propanoate

SMILES

CCCCCCOC(=O)\N=C(\N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C3=NC=CC=C3)N2C)C=C1

References

Synthesis Reference

Christian Filser, Wolfgang Dersch, Rainer Hamm, Arndt Hausherr, Gunter Koch, Ulrich Scholz, Georg Zerban, "METHOD FOR PRODUCING AN INTERMEDIATE PRODUCT OF DABIGATRAN ETEXILATE." U.S. Patent US20110118471, issued May 19, 2011.

US20110118471

General References

1. 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. [Article]
2. 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. [Article]
3. 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. [Article]
4. Ebner T, Wagner K, Wienen W: Dabigatran acylglucuronide, the major human metabolite of dabigatran: in vitro formation, stability, and pharmacological activity. Drug Metab Dispos. 2010 Sep;38(9):1567-75. doi: 10.1124/dmd.110.033696. Epub 2010 Jun 15. [Article]
5. van Ryn J, Goss A, Hauel N, Wienen W, Priepke H, Nar H, Clemens A: The discovery of dabigatran etexilate. Front Pharmacol. 2013 Feb 12;4:12. doi: 10.3389/fphar.2013.00012. eCollection 2013. [Article]
6. Negrier C, Shima M, Hoffman M: The central role of thrombin in bleeding disorders. Blood Rev. 2019 Nov;38:100582. doi: 10.1016/j.blre.2019.05.006. Epub 2019 May 22. [Article]
7. Wienen W, Stassen JM, Priepke H, Ries UJ, Hauel N: In-vitro profile and ex-vivo anticoagulant activity of the direct thrombin inhibitor dabigatran and its orally active prodrug, dabigatran etexilate. Thromb Haemost. 2007 Jul;98(1):155-62. [Article]
8. Eisert WG, Hauel N, Stangier J, Wienen W, Clemens A, van Ryn J: Dabigatran: an oral novel potent reversible nonpeptide inhibitor of thrombin. Arterioscler Thromb Vasc Biol. 2010 Oct;30(10):1885-9. doi: 10.1161/ATVBAHA.110.203604. Epub 2010 Jul 29. [Article]
9. Stangier J: Clinical pharmacokinetics and pharmacodynamics of the oral direct thrombin inhibitor dabigatran etexilate. Clin Pharmacokinet. 2008;47(5):285-95. doi: 10.2165/00003088-200847050-00001. [Article]
10. Vinholt PJ, Nielsen C, Soderstrom AC, Brandes A, Nybo M: Dabigatran reduces thrombin-induced platelet aggregation and activation in a dose-dependent manner. J Thromb Thrombolysis. 2017 Aug;44(2):216-222. doi: 10.1007/s11239-017-1512-2. [Article]
11. Trabold K, Makhoul S, Gambaryan S, van Ryn J, Walter U, Jurk K: The Direct Thrombin Inhibitors Dabigatran and Lepirudin Inhibit GPIbalpha-Mediated Platelet Aggregation. Thromb Haemost. 2019 Jun;119(6):916-929. doi: 10.1055/s-0039-1685139. Epub 2019 Apr 20. [Article]
12. Blech S, Ebner T, Ludwig-Schwellinger E, Stangier J, Roth W: The metabolism and disposition of the oral direct thrombin inhibitor, dabigatran, in humans. Drug Metab Dispos. 2008 Feb;36(2):386-99. doi: 10.1124/dmd.107.019083. Epub 2007 Nov 15. [Article]
13. Hu ZY, Parker RB, Herring VL, Laizure SC: Conventional liquid chromatography/triple quadrupole mass spectrometry based metabolite identification and semi-quantitative estimation approach in the investigation of in vitro dabigatran etexilate metabolism. Anal Bioanal Chem. 2013 Feb;405(5):1695-704. doi: 10.1007/s00216-012-6576-4. Epub 2012 Dec 14. [Article]
14. Laizure SC, Parker RB, Herring VL, Hu ZY: Identification of carboxylesterase-dependent dabigatran etexilate hydrolysis. Drug Metab Dispos. 2014 Feb;42(2):201-6. doi: 10.1124/dmd.113.054353. Epub 2013 Nov 8. [Article]
15. De Simone G, Pasquadibisceglie A, di Masi A, Buzzelli V, Trezza V, Macari G, Polticelli F, Ascenzi P: Binding of direct oral anticoagulants to the FA1 site of human serum albumin. J Mol Recognit. 2021 Mar;34(3):e2877. doi: 10.1002/jmr.2877. Epub 2020 Oct 9. [Article]
16. Bauer KA: New oral anticoagulants in development: potential for improved safety profiles. Rev Neurol Dis. 2010;7(1):1-8. [Article]
17. FDA Drug Approval Package for Dabigatran Etexilate [Link]
18. FDA Approved Drug Products: PRADAXA (dabigatran) oral pellets [Link]
19. FDA Approved Drug Products: PRADAXA (dabigatran) oral capsules [Link]
20. EMA Approved Drug Products: Dabigatran etexilate capsules for oral use [Link]
21. FDA Approved Drug Products: Pradaxa (dabigatran etexilate) oral pellets (November 2023) [Link]
22. Apotex Inc. Product Monograph: Dabigatran Etexilate [File]

External Links

Human Metabolome Database

HMDB0015641

KEGG Drug

D07144

PubChem Compound

6445226

PubChem Substance

99443249

ChemSpider

4948999

BindingDB

50432209

RxNav

1037042

ChEBI

70746

ChEMBL

CHEMBL539697

ZINC

ZINC000003943279

PharmGKB

PA165958369

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Dabigatran

FDA label

Download (731 KB)

MSDS

Download (99.2 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Arthroplasties, Replacement / Moderate Renal Impairment (CrCl 30-50 mL/Min) / Prevention of Venous Thromboembolism	1
4	Completed	Prevention	Atrial Fibrillation / Venous Thromboembolism	1
4	Completed	Treatment	Atrial Fibrillation	1
4	Recruiting	Basic Science	Chronic Kidney Disease (CKD)	1
4	Recruiting	Prevention	Atrial Fibrillation / Atrial Flutter	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Capsule, coated pellets	Oral	150 mg/1
Capsule, coated pellets	Oral	75 mg/1
Capsule	Oral
Capsule	Oral	110 mg/1
Capsule	Oral	150 mg/1
Capsule	Oral	20 mg
Capsule	Oral	30 mg
Capsule	Oral	40 mg
Capsule	Oral	50 mg
Capsule	Oral	6.25 mg/ml
Capsule	Oral	75 mg/1
Pellet	Oral	110 mg/1
Pellet	Oral	150 mg/1
Pellet	Oral	20 mg/1
Pellet	Oral	30 mg/1
Pellet	Oral	40 mg/1
Pellet	Oral	50 mg/1
Capsule	Oral	150.00 mg
Capsule, coated	Oral	150 mg
Capsule	Oral	86.4800 mg
Capsule	Oral	110 mg
Capsule	Oral	150 mg
Capsule	Oral	75 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US9034822	Yes	2015-05-19	2031-07-20
US6087380	Yes	2000-07-11	2022-06-28
US7932273	Yes	2011-04-26	2026-03-07
US7866474	Yes	2011-01-11	2028-03-02
US9925174	Yes	2018-03-27	2023-12-14

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	132	http://www.chemspider.com/Chemical-Structure.8615298.html
water solubility	1.8mg/ml, partly soluble	MSDS
logP	3.8	Apotex Inc. Product Monograph: Dabigatran Etexilate

Predicted Properties

Property	Value	Source
Water Solubility	0.00466 mg/mL	ALOGPS
logP	5.17	ALOGPS
logP	4.59	Chemaxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	17.89	Chemaxon
pKa (Strongest Basic)	4.48	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	154.03 Å2	Chemaxon
Rotatable Bond Count	17	Chemaxon
Refractivity	176.43 m3·mol-1	Chemaxon
Polarizability	70.65 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.942
Blood Brain Barrier	+	0.8673
Caco-2 permeable	-	0.7014
P-glycoprotein substrate	Substrate	0.7412
P-glycoprotein inhibitor I	Inhibitor	0.7539
P-glycoprotein inhibitor II	Inhibitor	0.8443
Renal organic cation transporter	Non-inhibitor	0.701
CYP450 2C9 substrate	Non-substrate	0.858
CYP450 2D6 substrate	Non-substrate	0.837
CYP450 3A4 substrate	Substrate	0.6154
CYP450 1A2 substrate	Non-inhibitor	0.6906
CYP450 2C9 inhibitor	Non-inhibitor	0.5102
CYP450 2D6 inhibitor	Non-inhibitor	0.8417
CYP450 2C19 inhibitor	Inhibitor	0.5157
CYP450 3A4 inhibitor	Inhibitor	0.781
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5789
Ames test	Non AMES toxic	0.6292
Carcinogenicity	Non-carcinogens	0.8065
Biodegradation	Not ready biodegradable	0.9931
Rat acute toxicity	2.7093 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9047
hERG inhibition (predictor II)	Inhibitor	0.6181

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001v-3234390000-c2177c303cbef52afbdf
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-004r-0292116000-55b368cbe92da888e681
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00kk-0981100000-78856b63936cf67ebce2
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004r-0292116000-55b368cbe92da888e681
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01t9-0000159000-2d8b185a0771561c3686
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0uk9-3600961000-f67905cc6ad0480d8cdf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f9x-1001950000-83779297ca27ce33a867
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0089-0000910000-cbf91e3fbb1a3ab475f4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a59-4624951000-d2340320b9ee3ae4dc77
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0fk9-0001910000-9f92bb49c4ea986a5e97

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	288.6733835	predicted	DarkChem Lite v0.1.0
[M-H]-	286.9361835	predicted	DarkChem Lite v0.1.0
[M-H]-	244.78325	predicted	DeepCCS 1.0 (2019)
[M+H]+	288.4650835	predicted	DarkChem Lite v0.1.0
[M+H]+	287.0547835	predicted	DarkChem Lite v0.1.0
[M+H]+	246.60814	predicted	DeepCCS 1.0 (2019)
[M+Na]+	287.2686835	predicted	DarkChem Lite v0.1.0
[M+Na]+	286.4765835	predicted	DarkChem Lite v0.1.0
[M+Na]+	252.21405	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Prothrombin

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

Curator comments

Dabigatran is a reversible, dose-dependent, competitive thrombin inhibitor with a Ki of 4.5 ± 0.2 nmol/L. In addition, the various acyl glucuronide metabolites of dabigatran also display in vitro activity.

General Function

Thrombospondin receptor activity

Specific Function

Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostas...

Gene Name

F2

Uniprot ID

P00734

Uniprot Name

Prothrombin

Molecular Weight

70036.295 Da

References

1. Squizzato A, Dentali F, Steidl L, Ageno W: New direct thrombin inhibitors. Intern Emerg Med. 2009 Dec;4(6):479-84. doi: 10.1007/s11739-009-0314-8. Epub 2009 Sep 15. [Article]
2. Liesenfeld KH, Schafer HG, Troconiz IF, Tillmann C, Eriksson BI, Stangier J: Effects of the direct thrombin inhibitor dabigatran on ex vivo coagulation time in orthopaedic surgery patients: a population model analysis. Br J Clin Pharmacol. 2006 Nov;62(5):527-37. [Article]
3. Karthikeyan G, Eikelboom JW, Hirsh J: Dabigatran: ready for prime time? Pol Arch Med Wewn. 2010 Apr;120(4):137-42. [Article]
4. Wienen W, Stassen JM, Priepke H, Ries UJ, Hauel N: In-vitro profile and ex-vivo anticoagulant activity of the direct thrombin inhibitor dabigatran and its orally active prodrug, dabigatran etexilate. Thromb Haemost. 2007 Jul;98(1):155-62. [Article]
5. Ebner T, Wagner K, Wienen W: Dabigatran acylglucuronide, the major human metabolite of dabigatran: in vitro formation, stability, and pharmacological activity. Drug Metab Dispos. 2010 Sep;38(9):1567-75. doi: 10.1124/dmd.110.033696. Epub 2010 Jun 15. [Article]
6. Eisert WG, Hauel N, Stangier J, Wienen W, Clemens A, van Ryn J: Dabigatran: an oral novel potent reversible nonpeptide inhibitor of thrombin. Arterioscler Thromb Vasc Biol. 2010 Oct;30(10):1885-9. doi: 10.1161/ATVBAHA.110.203604. Epub 2010 Jul 29. [Article]
7. FDA Approved Drug Products: PRADAXA (dabigatran) oral pellets [Link]
8. FDA Approved Drug Products: PRADAXA (dabigatran) oral capsules [Link]

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Drug created at May 03, 2010 18:25 / Updated at February 20, 2024 23:54