DABIGATRAN ETEXILATE

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

Structure Search

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)

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24212379https://www.drugbank.ca/drugs/DB06695
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Acyl coenzyme A:cholesterol acyltransferase 15 Target ID: CHEMBL2265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24212379	Substrate 661
Thrombin 21 Target ID: CHEMBL204 Sources: https://www.drugbank.ca/drugs/DB06695 \| http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022512s007lbl.pdf	Inhibitor 8504	1.2 nM [IC50]
Quinone reductase 2 12 Target ID: CHEMBL3959 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22494098 \|https://www.ncbi.nlm.nih.gov/pubmed/22494098	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Systemic embolism in patients with non-valvular atrial fibrillation 6 Sources: http://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Pradaxa/Pradaxa.pdf	Preventing	Approved 8583	PRADAXA Approved Use PRADAXA 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 Date 2010
Deep venous thrombosis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022512s007lbl.pdf	Primary	Approved 8583	PRADAXA Approved Use PRADAXA 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 Date 2010
Pulmonary embolism 19 Sources: http://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Pradaxa/Pradaxa.pdf	Preventing	Approved 8583	PRADAXA Approved Use PRADAXA 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 Date 2010
Unknown 2596

C_max

Value	Dose	Co-administered	Analyte	Population
348 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/18399711/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/18399711/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.3 h REVIEW https://pubmed.ncbi.nlm.nih.gov/18399711/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
65% REVIEW https://pubmed.ncbi.nlm.nih.gov/18399711/	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: https://pubmed.ncbi.nlm.nih.gov/17506785	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17506785	Sources: https://pubmed.ncbi.nlm.nih.gov/17506785
400 mg single, oral Highest studied dose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17506785	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17506785	Sources: https://pubmed.ncbi.nlm.nih.gov/17506785
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: https://pubmed.ncbi.nlm.nih.gov/32474728	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32474728	Disc. AE: C-reactive protein increased, Alanine aminotransferase increase... AEs leading to discontinuation/dose reduction: C-reactive protein increased (7.14%) Alanine aminotransferase increase (7.14%) Haematuria (7.14%) Epistaxis (7.14%) Haemorrhoidal haemorrhage (7.14%) Sources: https://pubmed.ncbi.nlm.nih.gov/32474728
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	Disc. AE: Spinal epidural hematoma, Bleeding... AEs leading to discontinuation/dose reduction: Spinal epidural hematoma Bleeding (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	Disc. AE: Bleeding, Gastrointestinal disorder NOS... AEs leading to discontinuation/dose reduction: Bleeding Gastrointestinal disorder NOS Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (grade 5, 0.07%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf

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: https://pubmed.ncbi.nlm.nih.gov/32474728	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32474728
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: https://pubmed.ncbi.nlm.nih.gov/32474728	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32474728
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: https://pubmed.ncbi.nlm.nih.gov/32474728	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32474728
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: https://pubmed.ncbi.nlm.nih.gov/32474728	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32474728
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: https://pubmed.ncbi.nlm.nih.gov/32474728	healthy, 18–45 Health Status: healthy Age Group: 18–45 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32474728
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022512s027lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 70 CYP2B6 926 CYP2C19 2057 CYP2E1 1060 CYP4A11 21 P-gp 1741	CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C19 1119 CYP2E1 729 CYP4A11 137 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 UGT2B17 237 P-gp 2052	CYP2B6 669 CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
CYP1A 122	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP4A11 25	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=68, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: 68-69, (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no [IC50 >100 uM]
CYP1A2 2333	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=110 Page: (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 110	no
CYP2B6 1160	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=110 Page: (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 110	no
CYP3A4 2633	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=110 Page: (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 110	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=55, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=34, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=68 Page: 54-56, 56-57, (PMDA_A100_1 Japanese) 34, (PMDA_I100-_ Japanese) 68	no

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A1 389	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no
CYP1A2 1197	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no
CYP2A6 626	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no
CYP2B6 776	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no
CYP2C19 1119	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no
CYP2E1 729	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no
CYP4A11 137	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (PMDA_A100_1 Japanese) 32, (PMDA_I100-_ Japanese) 33	no
UGT1A1 479	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT1A10 331	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT1A3 470	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT1A4 399	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT1A6 343	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT1A7 249	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT1A8 323	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT2B17 237	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
UGT2B4 278	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	no
CYP3A4 1946	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 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%. Sources: https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=32, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=33 Page: (ClinPharm) 13, (PMDA_A100_1 Japanese) 32, 40-41, (PMDA_I100_1 Japanese) 33
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=55, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000ClinPharmR_Corrrected%203.11.2011.pdf#page=12, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000ClinPharmR_Corrrected%203.11.2011.pdf#page=34, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=66, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_K103_1.pdf#page=154 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%. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=55, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000ClinPharmR_Corrrected%203.11.2011.pdf#page=12, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000ClinPharmR_Corrrected%203.11.2011.pdf#page=34, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=66, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_K103_1.pdf#page=154 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
UGT1A9 423	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	yes [Km 371.4 uM]
UGT2B15 236	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 Page: 70-71, (PMDA_A100_1 Japanese) 33, (PMDA_I100-_ Japanese) 101	yes [Km 511.7 uM]
UGT2B7 456	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=70, https://www.pmda.go.jp/drugs/2011/P201100019/530353000_22300AMX00433000_A100_1.pdf#page=33, https://www.pmda.go.jp/drugs/2011/P201100019/53035300_22300AMX00433000_I100_1.pdf#page=101 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
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022512Orig1s000PharmR_Corrrected%203.11.2011.pdf#page=47 Page: 15, 47

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:70752	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:70752
ChemicalBook	CB61458206	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61458206
eMolecules	31592368	https://www.emolecules.com/cgi-bin/more?vid=31592368
MolPort	MolPort-008-155-829	https://www.molport.com/shop/molecule-link/MolPort-008-155-829
Selleck Chemicals	BIBR-953(Dabigatran)	http://www.selleckchem.com/products/BIBR-953(Dabigatran).html
ZINC	ZINC000001910616	http://zinc15.docking.org/substances/ZINC000001910616

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	15831779
Emerging anticoagulants: mechanism of action and future potential.	2006 Mar	16637459
[Clinical use of a new class of anticoagulant drugs: the direct thrombin inhibitors].	2006 Nov	17216915
[New antitoagulants].	2007 Mar	17404541
Population pharmacokinetic analysis of the new oral thrombin inhibitor dabigatran etexilate (BIBR 1048) in patients undergoing primary elective total hip replacement surgery.	2007 Mar	17322149
Clinical pharmacokinetics and pharmacodynamics of the oral direct thrombin inhibitor dabigatran etexilate.	2008	18399711
Advancement in antithrombotics for stroke prevention in atrial fibrillation.	2008 Aug	18425569
Use of emerging oral anticoagulants in clinical practice: translating results from clinical trials to orthopedic and general surgical patient populations.	2009 Aug	19638915
Recent developments in the use of oral anticoagulants.	2009 Aug	19548861
Favorable therapeutic index of the direct factor Xa inhibitors, apixaban and rivaroxaban, compared with the thrombin inhibitor dabigatran in rabbits.	2009 Aug	19500242
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	19926603
[New oral anticoagulants. Consequences for perioperative coagulation diagnostics and therapy].	2009 Dec	19823782
Oral thrombin inhibitor dabigatran etexilate vs North American enoxaparin regimen for prevention of venous thromboembolism after knee arthroplasty surgery.	2009 Jan	18534438
New anticoagulants: focus on venous thromboembolism.	2009 Jul	19601856
Dabigatran: new drug. Continue to use heparin, a better-known option.	2009 Jun	19637411
[Venous thromboembolism prophylaxis in orthopaedics and traumatology].	2009 Mar	19378847
The prevention of hospital-acquired venous thromboembolism in the United Kingdom.	2009 Mar	19076173
Replacing aspirin and warfarin for secondary stroke prevention: is it worth the costs?	2010 Feb	19949330
Comparative efficacy and safety of the novel oral anticoagulants dabigatran, rivaroxaban and apixaban in preclinical and clinical development.	2010 Mar	20135071
[Oral prevention of thromboembolism with rivaroxaban and dabigatran: are the newly approved drugs innovations in orthopaedic and trauma surgery? ].	2010 Sep	20135622
Dabigatran and dabigatran ethyl ester: potent inhibitors of ribosyldihydronicotinamide dehydrogenase (NQO2).	2012 Apr 26	22494098

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:29:43 GMT 2025` Edited by `admin` on `Mon Mar 31 18:29:43 GMT 2025`
Record UNII	2E18WX195X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRADAXA

Preferred Name

English

DABIGATRAN ETEXILATE

Official Name

English

DABIGATRAN ETEXILATE [MART.]

Common Name

English

BIBR-1048

Code

English

DABIGATRAN ETEXILATE [VANDF]

Common Name

English

PRADAXA (DABIGATRAN ETEXILATE)

Common Name

English

dabigatran etexilate [INN]

Common Name

English

BIBR1048

Code

English

ETHYL 3-(((2-(((4-((((HEXYLOXY)CARBONYL)AMINO)IMINOMETHYL)PHENYL)AMINO)METHYL)-1-METHYL-1H-BENZIMIDAZOL-5-YL)CARBONYL)(PYRIDIN-2-YL)AMINO)PROPANOATE

Systematic Name

English

Dabigatran etexilate [WHO-DD]

Common Name

English

.BETA.-ALANINE, N-((2-(((4-((((HEXYLOXY)CARBONYL)AMINO)IMINOMETHYL)PHENYL)AMINO)METHYL)-1-METHYL-1H-BENZIMIDAZOL-5-YL)CARBONYL)-N-2-PYRIDINYL-, ETHYL ESTER

Common Name

English

BIBR 1048 BS RS1

Code

English

PRAZAXA

Brand Name

English

DABIGATRAN ETEXILATE METHANESULFONATE [JAN]

Common Name

English

DABIGATRAN ETEXILATE [MI]

Common Name

English

DABIGATRAN ETEXILATE [USAN]

Common Name

English

BIBR-1048-BS-RS1

Code

English

Ethyl 3-{[(2-{[(4-{[(hexyloxy)carbonyl]carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](pyridin-2-yl)amino}propanoate

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C263