Details
Stereochemistry | ACHIRAL |
Molecular Formula | C34H41N7O5 |
Molecular Weight | 627.7332 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCOC(=O)NC(=N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)N2C)C=C1
InChI
InChIKey=KSGXQBZTULBEEQ-UHFFFAOYSA-N
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)
Molecular Formula | C34H41N7O5 |
Molecular Weight | 627.7332 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022512s007lbl.pdf
https://www.pradaxa.com/
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022512s007lbl.pdf
https://www.pradaxa.com/
Dabigatran (Pradaxa, Prazaxa) is an anticoagulant medication that can be taken by mouth. FDA approved on October 19, 2010. 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). It may increase INR but this laboratory parameter is relatively insensitive to the activity of dabigatran. 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). 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). Contraindications: severe renal impairment (CrCL < 30 ml/min); haemorrhagic manifestations, bleeding diathesis or spontaneous or pharmacologic impairment of haemostasis; lesions at risk of clinically significant bleeding (e.g. extensive cerebral infarction (haemorrhagic or ischemic) in the last 6 months, active peptic ulcer disease); concomitant treatment with P-glycoprotein inhibitors (e.g. oral ketoconazole, verapamil); and those with known hypersensitivity to dabigatran, dabigatran etexilate or any ingredient used in the formulation or component of the container. As of December 2012, dabigatran is contraindicated in patients with mechanical prosthetic heart valves.
CNS Activity
Sources: http://cardiobrief.org/2010/11/07/re-ly-substudy-finds-dabigatran-effective-in-secondary-stroke-prevention/
Curator's Comment: Dabigatran doesn’t cross the blood-brain barrier.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24212379 |
|||
Target ID: CHEMBL204 |
1.2 nM [IC50] | ||
Target ID: CHEMBL3959 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | PRADAXA Approved UsePRADAXA is a direct thrombin inhibitor indicated:
To reduce the risk of stroke and systemic embolism in patients with non-valvular atrial fibrillation (1.1)
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 (1.2)
To reduce the risk of recurrence of DVT and PE in patients who have been previously treated (1.3)
For the prophylaxis of DVT and PE in patients who have undergone hip replacement surgery Launch Date2010 |
|||
Primary | PRADAXA Approved UsePRADAXA is a direct thrombin inhibitor indicated:
To reduce the risk of stroke and systemic embolism in patients with non-valvular atrial fibrillation (1.1)
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 (1.2)
To reduce the risk of recurrence of DVT and PE in patients who have been previously treated (1.3)
For the prophylaxis of DVT and PE in patients who have undergone hip replacement surgery Launch Date2010 |
|||
Preventing | PRADAXA Approved UsePRADAXA is a direct thrombin inhibitor indicated:
To reduce the risk of stroke and systemic embolism in patients with non-valvular atrial fibrillation (1.1)
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 (1.2)
To reduce the risk of recurrence of DVT and PE in patients who have been previously treated (1.3)
For the prophylaxis of DVT and PE in patients who have undergone hip replacement surgery Launch Date2010 |
|||
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
348 ng/mL |
150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DABIGATRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2232 ng × h/mL |
150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DABIGATRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.3 h |
150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DABIGATRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
65% |
150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DABIGATRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
400 mg 3 times / day single, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: single Dose: 400 mg, 3 times / day Sources: |
healthy, 18–45 |
|
400 mg single, oral Highest studied dose |
healthy, 18–45 |
|
150 mg 6 times / day multiple, oral Recommended Dose: 150 mg, 6 times / day Route: oral Route: multiple Dose: 150 mg, 6 times / day Sources: |
healthy, 18–45 |
Disc. AE: C-reactive protein increased, Alanine aminotransferase increase... AEs leading to discontinuation/dose reduction: C-reactive protein increased (7.14%) Sources: Alanine aminotransferase increase (7.14%) Haematuria (7.14%) Epistaxis (7.14%) Haemorrhoidal haemorrhage (7.14%) |
150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Spinal epidural hematoma, Bleeding... AEs leading to discontinuation/dose reduction: Spinal epidural hematoma Sources: Bleeding (grade 3-5) |
150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Bleeding, Gastrointestinal disorder NOS... AEs leading to discontinuation/dose reduction: Bleeding Sources: Gastrointestinal disorder NOS |
150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (grade 5, 0.07%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Alanine aminotransferase increase | 7.14% Disc. AE |
150 mg 6 times / day multiple, oral Recommended Dose: 150 mg, 6 times / day Route: oral Route: multiple Dose: 150 mg, 6 times / day Sources: |
healthy, 18–45 |
C-reactive protein increased | 7.14% Disc. AE |
150 mg 6 times / day multiple, oral Recommended Dose: 150 mg, 6 times / day Route: oral Route: multiple Dose: 150 mg, 6 times / day Sources: |
healthy, 18–45 |
Epistaxis | 7.14% Disc. AE |
150 mg 6 times / day multiple, oral Recommended Dose: 150 mg, 6 times / day Route: oral Route: multiple Dose: 150 mg, 6 times / day Sources: |
healthy, 18–45 |
Haematuria | 7.14% Disc. AE |
150 mg 6 times / day multiple, oral Recommended Dose: 150 mg, 6 times / day Route: oral Route: multiple Dose: 150 mg, 6 times / day Sources: |
healthy, 18–45 |
Haemorrhoidal haemorrhage | 7.14% Disc. AE |
150 mg 6 times / day multiple, oral Recommended Dose: 150 mg, 6 times / day Route: oral Route: multiple Dose: 150 mg, 6 times / day Sources: |
healthy, 18–45 |
Spinal epidural hematoma | Disc. AE | 150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Bleeding | grade 3-5 Disc. AE |
150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Bleeding | Disc. AE | 150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Gastrointestinal disorder NOS | Disc. AE | 150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Bleeding | grade 5, 0.07% Disc. AE |
150 mg 2 times / day multiple, oral Recommended Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no [IC50 >100 uM] | |||
Page: (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 110 |
no | |||
Page: (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 110 |
no | |||
Page: (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 110 |
no | |||
Page: 54-56, 56-57, (PMDA_A100_1 Japanese) 34, (PMDA_I100-_ Japanese) 68 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no | |||
Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no | |||
Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no | |||
Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no | |||
Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no | |||
Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no | |||
Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
no | |||
Page: (ClinPharm) 13, (PMDA_A100_1 Japanese) 32, 40-41, (PMDA_I100_1 Japanese) 33 |
no | no (co-administration study) Comment: Coadministration of Atorvastatin (CYP3A4 & P-gp inhibitor, 400 mg QD x 4 days) with Dabigatran metexilate mesylate (150 mg BID x 3 days and 150 mg QD on Day 4) decreased total Dabigatran AUCtau,ss by 58% and Cmax,ss by 50%., Coadministration of Clarithromycin (CYP3A4 & P-gp inhibitor, 500 mg BID x 5 days & 500 mg QD on Day 6) with Dabigatran metexilate mesylate (150 mg QD on Day 6) increased total Dabigatran AUCinf by 19% and Cmax by 15%., Coadministration of Rifampicin (CYP3A4 & P-gp inducer, 600 mg QD x 7 days in the night) with Dabigatran metexilate mesylate (150 mg QD on Day 8 morning) decreased total Dabigatran AUCinf by 67% and Cmax by 66%., Coadministration of Ketoconazole (CYP3A4 & P-gp inhibitor, 400mg QD ) with Dabigatran metexilate mesylate (150 mg QD) increased total Dabigatran AUCinf by 138% and Cmax by 135%. Page: (ClinPharm) 13, (PMDA_A100_1 Japanese) 32, 40-41, (PMDA_I100_1 Japanese) 33 |
||
Page: 54-55, 56-57, (ClinPharm) 12, 13, 33-36, (PMDA_A100_1 Japanese) 33, 39, 40-41, (PMDA_I100_1 Japanese) 66, (PMDA_K103_1 Japanese) 152-156 |
no | no (co-administration study) Comment: Caco-2 cells, Efflux ratio = 1.09 (3 mcM), 0.95 (300 mcM); MDR1-LLC-PK1 cells, Efflux ratio = 1.35 (10 mcM); Coadministration of Amiodarone (P-gp & CYP2C9 inhibitor, 600 mg QD on Day 4) with Dabigatran metexilate mesylate (150 mg BID x 3 days and 150 mg QD on Day 4) increased total Dabigatran AUCtau,ss by 58% and Cmax by 50%., Coadministration of Verapamil (P-gp inhibitor, 120 mg single or multiple doses, or 240 mg single dose) with Dabigatran metexilate mesylate (150 mg single dose) increased total Dabigatran AUCinf by 39~143% and Cmax by 12~179%., Coadministration of Quinidine (200 mg every 2 hr x 5 on Day 3 (3 hr after the first Dabigatran dose), P-gp inhibitor) with Dabigatran metexilate mesylate (150 mg BID x 3 days (2nd dose on Day 3 was administrated 1 hr after the final Quinidine dose) increased total Dabigatran AUCtau,ss by 53% and Cmax,ss by 56%., Coadministration of Ketoconazole (CYP3A4 & P-gp inhibitor, 400mg QD ) with Dabigatran metexilate mesylate (150 mg QD) increased total Dabigatran AUCinf by 138% and Cmax by 135%., Coadministration of Atorvastatin (CYP3A4 & P-gp inhibitor, 400 mg QD x 4 days) with Dabigatran metexilate mesylate (150 mg BID x 3 days and 150 mg QD on Day 4) decreased total Dabigatran AUCtau,ss by 58% and Cmax,ss by 50%., Coadministration of Clarithromycin (CYP3A4 & P-gp inhibitor, 500 mg BID x 5 days & 500 mg QD on Day 6) with Dabigatran metexilate mesylate (150 mg QD on Day 6) increased total Dabigatran AUCinf by 19% and Cmax by 15%., Coadministration of Rifampicin (CYP3A4 & P-gp inducer, 600 mg QD x 7 days in the night) with Dabigatran metexilate mesylate (150 mg QD on Day 8 morning) decreased total Dabigatran AUCinf by 67% and Cmax by 66%. Page: 54-55, 56-57, (ClinPharm) 12, 13, 33-36, (PMDA_A100_1 Japanese) 33, 39, 40-41, (PMDA_I100_1 Japanese) 66, (PMDA_K103_1 Japanese) 152-156 |
||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
yes [Km 371.4 uM] | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
yes [Km 511.7 uM] | |||
Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101 |
yes [Km 987.3 uM] |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacokinetic profile of the oral direct thrombin inhibitor dabigatran etexilate in healthy volunteers and patients undergoing total hip replacement. | 2005 May |
|
Emerging anticoagulants: mechanism of action and future potential. | 2006 Mar |
|
[Clinical use of a new class of anticoagulant drugs: the direct thrombin inhibitors]. | 2006 Nov |
|
[New antitoagulants]. | 2007 Mar |
|
Population pharmacokinetic analysis of the new oral thrombin inhibitor dabigatran etexilate (BIBR 1048) in patients undergoing primary elective total hip replacement surgery. | 2007 Mar |
|
Clinical pharmacokinetics and pharmacodynamics of the oral direct thrombin inhibitor dabigatran etexilate. | 2008 |
|
Advancement in antithrombotics for stroke prevention in atrial fibrillation. | 2008 Aug |
|
Use of emerging oral anticoagulants in clinical practice: translating results from clinical trials to orthopedic and general surgical patient populations. | 2009 Aug |
|
Recent developments in the use of oral anticoagulants. | 2009 Aug |
|
Favorable therapeutic index of the direct factor Xa inhibitors, apixaban and rivaroxaban, compared with the thrombin inhibitor dabigatran in rabbits. | 2009 Aug |
|
Clinical trials update from the European Society of Cardiology Meeting 2009: AAA, RELY, PROTECT, ACTIVE-I, European CRT survey, German pre-SCD II registry, and MADIT-CRT. | 2009 Dec |
|
[New oral anticoagulants. Consequences for perioperative coagulation diagnostics and therapy]. | 2009 Dec |
|
Oral thrombin inhibitor dabigatran etexilate vs North American enoxaparin regimen for prevention of venous thromboembolism after knee arthroplasty surgery. | 2009 Jan |
|
New anticoagulants: focus on venous thromboembolism. | 2009 Jul |
|
Dabigatran: new drug. Continue to use heparin, a better-known option. | 2009 Jun |
|
[Venous thromboembolism prophylaxis in orthopaedics and traumatology]. | 2009 Mar |
|
The prevention of hospital-acquired venous thromboembolism in the United Kingdom. | 2009 Mar |
|
Replacing aspirin and warfarin for secondary stroke prevention: is it worth the costs? | 2010 Feb |
|
Comparative efficacy and safety of the novel oral anticoagulants dabigatran, rivaroxaban and apixaban in preclinical and clinical development. | 2010 Mar |
|
[Oral prevention of thromboembolism with rivaroxaban and dabigatran: are the newly approved drugs innovations in orthopaedic and trauma surgery? ]. | 2010 Sep |
|
Dabigatran and dabigatran ethyl ester: potent inhibitors of ribosyldihydronicotinamide dehydrogenase (NQO2). | 2012 Apr 26 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:29:43 GMT 2025
by
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on
Mon Mar 31 18:29:43 GMT 2025
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Record UNII |
2E18WX195X
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C263
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QB01AE07
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B01AE07
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1037042
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CHEMBL539697
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Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE -> PARENT |
after p.o. administration of 200 mg of 14C dabigatran etexilate in healthy volunteers
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
after p.o. administration of 200 mg of 14C dabigatran etexilate in healthy volunteers
FECAL
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METABOLITE ACTIVE -> PARENT |
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METABOLITE -> PARENT |
after p.o. administration of 200 mg of 14C dabigatran etexilate in healthy volunteers
FECAL
|
||
|
METABOLITE -> PARENT |
after p.o. administration of 200 mg of 14C dabigatran etexilate in healthy volunteers
TRACE AMOUNT
PLASMA; URINE
|
||
|
METABOLITE -> PARENT |
after p.o. administration of 200 mg of 14C dabigatran etexilate in healthy volunteers
FECAL
|
||
|
METABOLITE -> PARENT |
after p.o. administration of 200 mg of 14C dabigatran etexilate in healthy volunteers
TRACE AMOUNT
URINE
|
||
|
METABOLITE -> PARENT |
after p.o. administration of 200 mg of 14C dabigatran etexilate in healthy volunteers
TRACE AMOUNT
PLASMA
|
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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