Identification

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Name
Dabigatran etexilate
Accession Number
DB06695
Type
Small Molecule
Groups
Approved
Description

Dabigatran etexilate is an oral prodrug that is hydrolyzed to the competitive and reversible direct thrombin inhibitordabigatranLabel,5. Dabigatran etexilate may be used to decrease the risk of venous thromboembolic events in patients in whom anticoagulation therapy is indicated5. In contrast to warfarin, because its anticoagulant effects are predictable, lab monitoring is not necessary5. Dabigatran etexilate was approved by the FDA in 20106.

Structure
Thumb
Synonyms
  • Dabigatran etexilate
External IDs
BIBR 1048 / BIBR 1048 BS RS1 / BIBR-1048 / BIBR-1048-BS-RS1
Product Ingredients
IngredientUNIICASInChI Key
Dabigatran etexilate mesilateSC7NUW5IIT872728-81-9XETBXHPXHHOLOE-UHFFFAOYSA-N
Active Moieties
NameKindUNIICASInChI Key
DabigatranprodrugI0VM4M70GC211914-51-1YBSJFWOBGCMAKL-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PradaxaCapsule75 mg/1OralBoehringer Ingelheim Pharmaceuticals Inc.2010-11-082010-10-25Us
PradaxaCapsule110 mg/1OralBoehringer Ingelheim2015-11-23Not applicableUs
PradaxaCapsule110 mgOralBoehringer Ingelheim2008-03-18Not applicableEu
PradaxaCapsule150 mgOralBoehringer Ingelheim2008-03-18Not applicableEu
PradaxaCapsule110 mgOralBoehringer Ingelheim2008-03-18Not applicableEu
PradaxaCapsule75 mgOralBoehringer Ingelheim (Canada) Ltd Ltee2008-07-03Not applicableCanada
PradaxaCapsule75 mgOralBoehringer Ingelheim2008-03-18Not applicableEu
PradaxaCapsule110 mgOralBoehringer Ingelheim2008-03-18Not applicableEu
PradaxaCapsule75 mg/1OralBoehringer Ingelheim2011-08-08Not applicableUs
PradaxaCapsule150 mg/1OralBoehringer Ingelheim2017-07-28Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-dabigatranCapsule150 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-dabigatranCapsule110 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-dabigatranCapsule75 mgOralApotex CorporationNot applicableNot applicableCanada
Teva-dabigatranCapsule75 mgOralTevaNot applicableNot applicableCanada
Teva-dabigatranCapsule150 mgOralTevaNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Pradax (Boehringer Ingelheim) / Rendix
Categories
UNII
2E18WX195X
CAS number
211915-06-9
Weight
Average: 627.7332
Monoisotopic: 627.316917457
Chemical Formula
C34H41N7O5
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

Pharmacology

Indication

Dabigatran is indicated for the prevention of venous thromboembolic events in patients who have undergone elective hip or knee replacement surgery (based on RE-NOVATE, RE-MODEL, and RE-MOBILIZE trials)5,2,1. In 2010, it was approved in the US and Canada for prevention of stroke and systemic embolism in patients with atrial fibrillation (approval based on the RE-LY trial)Label,5.

Associated Conditions
Pharmacodynamics

Dabigatran directly inhibits thrombin in a concentration-dependent, reversible, specific, and competitive manner which results in a prolongation of aPTT (partial thromboplastin time), ECT (Ecarin clotting time), and TT (thrombin time)Label,5.

Mechanism of action

Dabigatran is hydrolysed to the active dabigatran by an esterase which induces hydrolysisLabel,4. Dabigatran and it's glucuronidated metabolites all share equal pharmacological activityLabel,4. Dabigatran and its metabolites inhibit thrombin, a serine proteaseLabel,4. This inhibition prevents the thrombin mediated conversion of fibrinogen to fibrin, an early step in the coagulation cascadeLabel,4. With reduced conversion of fibrinogen to fibrin, clotting time increases.

TargetActionsOrganism
AProthrombin
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Oral dabigatran is 3-7% bioavailable, reaching a maximum concentration 1 hour after administration in fasted subjectsLabel. When taken with a meal that is high in fat, the time to maximum concentration increases to 2 hours, though this does not affect dosingLabel,5. Dabigatran etexilate's bioavailability increases to 75% when taken without the capsule shell and so patients should not chew or crush the capsulesLabel.

Volume of distribution

50-70LLabel.

Protein binding

Dabigatran is approximately 35% protein plasma boundLabel,5.

Metabolism

Dabigatran etexilate is metabolised by esterases, microsomal carboxylesterases, and uridine 5'-diphospho-glucuronosyltransferases(UGTs)Label,4. Dabigatran etexilate undergoes hydrolysis to create the active dabigatran which is then glucuronidated by UGTs to 1-O, 2-O, 3-O, or 4-O-acylglucuronideLabel,4.

Route of elimination

7% of the dose is recovered in urine and 86% is recovered in the fecesLabel.

Half life

12 to 17 hoursLabel,5.

Clearance
Not Available
Toxicity

No human studies involving pregnancy, labor and delivery, nursing, or pediatricsLabel. Geriatric patients are at higher risk of adverse effects than younger patients but the risk to benefit ratio is generally still favourable for older patientsLabel. 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/minLabel.

In animal studies, dabigatran increases the rates of dead offspring and causes uterine and vaginal bleeding close to birthLabel. 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 consideredLabel.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1,2,6,7-3H)TestosteroneThe therapeutic efficacy of Dabigatran etexilate can be increased when used in combination with (1,2,6,7-3H)Testosterone.
(R)-warfarinDabigatran etexilate may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinDabigatran etexilate may increase the anticoagulant activities of (S)-Warfarin.
1-TestosteroneThe therapeutic efficacy of Dabigatran etexilate can be increased when used in combination with 1-Testosterone.
18-methyl-19-nortestosteroneThe therapeutic efficacy of Dabigatran etexilate can be increased when used in combination with 18-methyl-19-nortestosterone.
3,5-diiodothyropropionic acid3,5-diiodothyropropionic acid may increase the anticoagulant activities of Dabigatran etexilate.
4-hydroxycoumarinDabigatran etexilate may increase the anticoagulant activities of 4-hydroxycoumarin.
4-HydroxytestosteroneThe therapeutic efficacy of Dabigatran etexilate can be increased when used in combination with 4-Hydroxytestosterone.
5beta-dihydrotestosteroneThe therapeutic efficacy of Dabigatran etexilate can be increased when used in combination with 5beta-dihydrotestosterone.
6-Deoxyerythronolide BThe metabolism of Dabigatran etexilate can be decreased when combined with 6-Deoxyerythronolide B.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
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Food Interactions
  • St. John's Wort

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. [PubMed:17764540]
  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. [PubMed:17869635]
  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. [PubMed:23292752]
  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. [PubMed:20551237]
  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. [PubMed:23408233]
  6. FDA Drug Approval Package for Dabigatran Etexilate [Link]
  7. 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
ChEBI
70746
ChEMBL
CHEMBL539697
PharmGKB
PA165958369
Wikipedia
Dabigatran
ATC Codes
B01AE07 — Dabigatran etexilate
AHFS Codes
  • 20:12.04.12 — Direct Thrombin Inhibitors
FDA label
Download (731 KB)
MSDS
Download (99.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentHealthy Volunteers1
1CompletedNot AvailableCardiovascular Disease (CVD) / Chronic Renal Failure (CRF)1
1CompletedNot AvailableHealthy Volunteers2
1CompletedBasic ScienceDisorders, Blood Coagulation1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedOtherHealthy Volunteers2
1CompletedOtherProstatic Neoplasms1
1CompletedTreatmentHealthy Volunteers30
1CompletedTreatmentHepatic Insufficiency1
1CompletedTreatmentImpaired Renal Function1
1CompletedTreatmentInterstitial Lung Disease (ILD) / Scleroderma1
1CompletedTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD)1
1CompletedTreatmentRenal Insufficiency,Chronic1
1CompletedTreatmentThrombotic events1
1Not Yet RecruitingTreatmentAcute Pancreatitis (AP)1
1Not Yet RecruitingTreatmentMild Alzheimer's Disease / Mild Cognitive Impairment (MCI)1
1TerminatedTreatmentHealthy Volunteers1
2CompletedNot AvailableVenous Thromboembolism (VTE)2
2CompletedPreventionArthroplasty, Replacement, Knee / Thrombosis, Venous1
2CompletedPreventionNonvalvular Atrial Fibrillation1
2CompletedPreventionVenous Thromboembolism (VTE)1
2CompletedTreatmentCoronary Heart Disease (CHD)1
2CompletedTreatmentHeart Catheterization1
2CompletedTreatmentMinor Ischemic Stroke / Transient Ischaemic Attack (TIA)2
2CompletedTreatmentVenous Thromboembolism (VTE)3
2TerminatedPreventionHeart Valve Diseases1
2TerminatedPreventionHeart Valve Prosthesis / Thromboembolism1
2TerminatedPreventionNonvalvular Atrial Fibrillation / Strokes1
2TerminatedTreatmentBleeding / Thrombotic events1
2Unknown StatusTreatmentCerebral autosomal dominant arteriopathy with subcortical infarcts and leukoencephalopathy1
2WithdrawnTreatmentVenous Thromboembolism (VTE)1
2, 3TerminatedTreatmentPrimary Disease1
3Active Not RecruitingTreatmentMyocardial Injury After Noncardiac Surgery (MINS)1
3CompletedPreventionArthroplasty, Replacement, Hip / Thromboembolism1
3CompletedPreventionArthroplasty, Replacement, Knee / Thromboembolism2
3CompletedPreventionSecondary Preventions / Strokes1
3CompletedPreventionVenous Thromboembolism (VTE)2
3CompletedTreatmentHematoma1
3CompletedTreatmentNonvalvular Atrial Fibrillation / Percutaneous Coronary Intervention1
3CompletedTreatmentThromboembolism4
3Not Yet RecruitingPreventionNonvalvular Atrial Fibrillation / Thromboembolism1
3Not Yet RecruitingTreatmentNonvalvular Atrial Fibrillation1
3RecruitingPreventionAtrial Flutter / Intracranial Hemorrhage, Hypertensive / Intracranial Hemorrhages / Intraventricular Hemorrhage / Microhaemorrhage / Nonvalvular Atrial Fibrillation / Small Vessel Cerebrovascular Disease / Subarachnoid Hemorrhage / Subdural haematoma1
3RecruitingPreventionSecondary Preventions / Venous Thromboembolism (VTE)1
3RecruitingTreatmentCerebral Venous Thrombosis1
3RecruitingTreatmentDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE) / Venous Thromboembolism (VTE)1
3RecruitingTreatmentVenous Thromboembolism (VTE)1
4Active Not RecruitingPreventionNonvalvular Atrial Fibrillation1
4Active Not RecruitingSupportive CareAtrial Flutter / Nonvalvular Atrial Fibrillation1
4CompletedBasic ScienceVenous Thromboembolism (VTE)1
4CompletedPreventionArthroplasty, Replacement / Moderate Renal Impairment (CrCl 30-50 mL/Min) / Prevention of Venous Thromboembolism1
4CompletedPreventionNonvalvular Atrial Fibrillation2
4CompletedTreatmentCoronary Heart Disease (CHD)1
4CompletedTreatmentNonvalvular Atrial Fibrillation4
4Enrolling by InvitationPreventionDevice Related Thrombus / Left Atrial Appendage Thrombosis / Nonvalvular Atrial Fibrillation / Watchman LAA Closure Device1
4Enrolling by InvitationTreatmentNonvalvular Atrial Fibrillation1
4RecruitingOtherCerebral Ischemic Events / Cognition Disorders / Dementias1
4RecruitingPreventionNonvalvular Atrial Fibrillation2
4RecruitingTreatment(Atrial Fibrillation) or (Atrial Flutter) / Thrombosis of Left Atrial Appendage1
4RecruitingTreatmentAngiographically Confirmed Acute Massive Pulmonary Embolism Treated With Endovascular Mechanical Fragmentation and Thrombolytic Therapy / Dabigatran Etexilate / Pulmonary Embolism (PE) / Recurrence of DVT / Warfarin1
4RecruitingTreatmentCardioembolic Events / Nonvalvular Atrial Fibrillation / Oral Anticoagulation1
4RecruitingTreatmentCoronary Artery Disease / Nonvalvular Atrial Fibrillation1
4RecruitingTreatmentDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE)1
4RecruitingTreatmentDiabetes Mellitus (DM)1
4RecruitingTreatmentLeft Atrial Thrombosis / Nonvalvular Atrial Fibrillation1
4RecruitingTreatmentNonvalvular Atrial Fibrillation2
4RecruitingTreatmentNonvalvular Atrial Fibrillation / Valve Heart Disease1
4RecruitingTreatmentPulmonary Embolism (PE)1
4TerminatedDiagnosticNonvalvular Atrial Fibrillation1
4TerminatedTreatmentAcute Coronary Syndromes (ACS) / Atherosclerosis / Coronary Heart Disease (CHD) / Nonvalvular Atrial Fibrillation1
4Unknown StatusNot AvailableAnticoagulant Overdosage / Anticoagulant-induced Bleeding / Hemorrhage / Thrombotic events1
4WithdrawnTreatmentCoronary Heart Disease (CHD) / Non ST Segment Elevation Myocardial Infarction (NSTEMI) / ST Elevation Myocardial Infarction (STEMI) / Stable Angina (SA) / Unstable Angina Pectoris1
4WithdrawnTreatmentThromboembolism1
Not AvailableActive Not RecruitingNot AvailableAnticoagulation1
Not AvailableActive Not RecruitingNot AvailableNon-valvular Atrial Fibrillation (NVAF)1
Not AvailableActive Not RecruitingNot AvailableNonvalvular Atrial Fibrillation3
Not AvailableCompletedNot AvailableAnticoagulants / Nonvalvular Atrial Fibrillation / Pharmacoepidemiology1
Not AvailableCompletedNot AvailableHemorrhage / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedNot AvailableMajor Bleeding / Myocardial Infarction / Nonvalvular Atrial Fibrillation / Stroke, Ischemic / Systemic Embolization / The Mortality Rate2
Not AvailableCompletedNot AvailableMajor Bleeding / Venous Thromboembolism (VTE)1
Not AvailableCompletedNot AvailableNonvalvular Atrial Fibrillation14
Not AvailableCompletedNot AvailableNonvalvular Atrial Fibrillation / Strokes Thrombotic1
Not AvailableCompletedNot AvailableStrokes1
Not AvailableCompletedNot AvailableStrokes / Transient Ischaemic Attack (TIA)1
Not AvailableCompletedNot AvailableUnsuspected Pulmonary Embolism1
Not AvailableCompletedTreatmentCoronary Artery Disease1
Not AvailableCompletedTreatmentNonvalvular Atrial Fibrillation1
Not AvailableEnrolling by InvitationTreatmentAnticoagulant Adverse Reaction / Hemorrhage / Nonvalvular Atrial Fibrillation / Thrombotic events1
Not AvailableNot Yet RecruitingNot AvailableCerebral Vein Thrombosis / Ovarian vein thrombosis / Renal Vein Thrombosis / Retinal Vein Thrombosis / Splanchnic Vein Thrombosis1
Not AvailableNot Yet RecruitingBasic ScienceIdiopathic Pulmonary Fibrosis (IPF) / Interstitial Lung Disease (ILD) / IPF1
Not AvailableNot Yet RecruitingTreatmentNonvalvular Atrial Fibrillation / Stroke, Acute1
Not AvailableRecruitingNot AvailableCardioembolic Stroke1
Not AvailableRecruitingHealth Services ResearchNeoplasms / Thrombosis, Venous1
Not AvailableRecruitingPreventionNonvalvular Atrial Fibrillation / Strokes1
Not AvailableRecruitingSupportive CareHemorrhage / Nonvalvular Atrial Fibrillation / Periodontal Diseases1
Not AvailableRecruitingTreatmentAcute DVT of Lower Extremity1
Not AvailableRecruitingTreatmentBlood Clots / Deep Vein Thrombosis (DVT) / Malignancies / Pulmonary Embolism (PE) / Venous Thromboembolism (VTE)1
Not AvailableTerminatedNot AvailableArthroplasty, Replacement / Venous Thromboembolism (VTE)1
Not AvailableUnknown StatusSupportive CareBlood Loss / Osteoarthritis, Hip1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral110 mg/1
CapsuleOral110 mg
CapsuleOral150 mg/1
CapsuleOral150 mg
CapsuleOral75 mg/1
CapsuleOral75 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US9034822No2015-05-192031-01-20Us
US6087380No2000-07-112018-02-18Us
US7932273No2011-04-262025-09-07Us
US7866474No2011-01-112027-08-31Us
US9925174No2018-03-272023-06-14Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)132http://www.chemspider.com/Chemical-Structure.8615298.html
water solubility1.8mg/ml, partly soluble MSDS
logP3.8Apotex Inc. Product Monograph: Dabigatran Etexilate
Predicted Properties
PropertyValueSource
Water Solubility0.00466 mg/mLALOGPS
logP5.17ALOGPS
logP4.59ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)17.89ChemAxon
pKa (Strongest Basic)4.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area154.03 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity176.43 m3·mol-1ChemAxon
Polarizability70.65 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.942
Blood Brain Barrier+0.8673
Caco-2 permeable-0.7014
P-glycoprotein substrateSubstrate0.7412
P-glycoprotein inhibitor IInhibitor0.7539
P-glycoprotein inhibitor IIInhibitor0.8443
Renal organic cation transporterNon-inhibitor0.701
CYP450 2C9 substrateNon-substrate0.858
CYP450 2D6 substrateNon-substrate0.837
CYP450 3A4 substrateSubstrate0.6154
CYP450 1A2 substrateNon-inhibitor0.6906
CYP450 2C9 inhibitorNon-inhibitor0.5102
CYP450 2D6 inhibitorNon-inhibitor0.8417
CYP450 2C19 inhibitorInhibitor0.5157
CYP450 3A4 inhibitorInhibitor0.781
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5789
Ames testNon AMES toxic0.6292
CarcinogenicityNon-carcinogens0.8065
BiodegradationNot ready biodegradable0.9931
Rat acute toxicity2.7093 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9047
hERG inhibition (predictor II)Inhibitor0.6181
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00kk-0981100000-78856b63936cf67ebce2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004r-0292116000-55b368cbe92da888e681

Taxonomy

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
show 10 more
Substituents
Benzimidazole / Aniline or substituted anilines / Phenylalkylamine / Secondary aliphatic/aromatic amine / Aralkylamine / Monocyclic benzene moiety / N-substituted imidazole / Pyridine / Benzenoid / Imidolactam
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carboxylic ester, carboxamidine, beta-alanine derivative, pyridines, aromatic amide, benzimidazoles (CHEBI:70746)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:19756950]
  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. [PubMed:17061960]
  3. Karthikeyan G, Eikelboom JW, Hirsh J: Dabigatran: ready for prime time? Pol Arch Med Wewn. 2010 Apr;120(4):137-42. [PubMed:20424539]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. 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. [PubMed:23239178]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Methylumbelliferyl-acetate deacetylase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and ...
Gene Name
CES2
Uniprot ID
O00748
Uniprot Name
Cocaine esterase
Molecular Weight
61806.41 Da
References
  1. 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. [PubMed:23239178]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. 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. [PubMed:20551237]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. 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. [PubMed:20551237]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. 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. [PubMed:20551237]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Nadph dehydrogenase (quinone) activity
Specific Function
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vi...
Gene Name
NQO2
Uniprot ID
P16083
Uniprot Name
Ribosyldihydronicotinamide dehydrogenase [quinone]
Molecular Weight
25918.4 Da
References
  1. Michaelis S, Marais A, Schrey AK, Graebner OY, Schaudt C, Sefkow M, Kroll F, Dreger M, Glinski M, Koester H, Metternich R, Fischer JJ: Dabigatran and dabigatran ethyl ester: potent inhibitors of ribosyldihydronicotinamide dehydrogenase (NQO2). J Med Chem. 2012 Apr 26;55(8):3934-44. doi: 10.1021/jm3001339. Epub 2012 Apr 17. [PubMed:22494098]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Galanis T, Thomson L, Palladino M, Merli GJ: New oral anticoagulants. J Thromb Thrombolysis. 2011 Apr;31(3):310-20. doi: 10.1007/s11239-011-0559-8. [PubMed:21327511]
  2. 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. [PubMed:23292752]

Drug created on May 03, 2010 12:25 / Updated on May 21, 2019 12:22