Dabigatran etexilate

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 inhibitor dabigatran^Label,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

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Dabigatran etexilate (DB06695)

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Synonyms

• Dabigatran etexilate

External IDs

BIBR 1048 / BIBR 1048 BS RS1 / BIBR-1048 / BIBR-1048-BS-RS1

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

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Pradaxa	Capsule	150 mg/1	Oral	Rebel Distributors	2010-10-26	Not applicable
Pradaxa	Capsule	110 mg	Oral	Boehringer Ingelheim	2008-03-18	Not applicable
Pradaxa	Capsule	150 mg	Oral	Boehringer Ingelheim	2008-03-18	Not applicable
Pradaxa	Capsule	150 mg/1	Oral	A-S Medication Solutions	2017-07-28	Not applicable
Pradaxa	Capsule	75 mg	Oral	Boehringer Ingelheim	2008-03-18	Not applicable
Pradaxa	Capsule	150 mg/1	Oral	Boehringer Ingelheim	2010-10-26	Not applicable
Pradaxa	Capsule	150 mg	Oral	Boehringer Ingelheim	2008-03-18	Not applicable
Pradaxa	Capsule	110 mg	Oral	Boehringer Ingelheim	2008-03-18	Not applicable
Pradaxa	Capsule	150 mg	Oral	Boehringer Ingelheim (Canada) Ltd Ltee	2010-11-03	Not applicable
Pradaxa	Capsule	110 mg	Oral	Boehringer Ingelheim	2008-03-18	Not applicable

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Apo-dabigatran	Capsule		Oral	Apotex Corporation	2019-02-04	Not applicable
Apo-dabigatran	Capsule		Oral	Apotex Corporation	2019-08-14	Not applicable
Apo-dabigatran	Capsule		Oral	Apotex Corporation	2019-02-04	Not applicable
Teva-dabigatran	Capsule		Oral	TEVA Canada Limited	Not applicable	Not applicable
Teva-dabigatran	Capsule		Oral	TEVA Canada Limited	Not applicable	Not applicable

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

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

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

• Deep Venous Thrombosis
• Deep vein thrombosis recurrent
• Pulmonary Embolism
• Recurrent pulmonary embolism
• Strokes
• Systemic Embolism

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 hydrolysis^Label,4. Dabigatran and it's glucuronidated metabolites all share equal pharmacological activity^Label,4. Dabigatran and its metabolites inhibit thrombin, a serine protease^Label,4. This inhibition prevents the thrombin mediated conversion of fibrinogen to fibrin, an early step in the coagulation cascade^Label,4. With reduced conversion of fibrinogen to fibrin, clotting time increases.

Target	Actions	Organism
AProthrombin	inhibitor	Humans

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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 subjects^Label. When taken with a meal that is high in fat, the time to maximum concentration increases to 2 hours, though this does not affect dosing^Label,5. Dabigatran etexilate's bioavailability increases to 75% when taken without the capsule shell and so patients should not chew or crush the capsules^Label.

Volume of distribution

50-70L^Label.

Protein binding

Dabigatran is approximately 35% protein plasma bound^Label,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-acylglucuronide^Label,4.

• Dabigatran etexilate
  Dabigatran
  • Dabigatran
    Dabigatran 1-O-acylglucuronide metabolite
  • Dabigatran
    Dabigatran 2-O-acylglucuronide metabolite
  • Dabigatran
    Dabigatran 3-O-acylglucuronide metabolite
  • Dabigatran
    Dabigatran 4-O-acylglucuronide metabolite

Route of elimination

7% of the dose is recovered in urine and 86% is recovered in the feces^Label.

Half life

12 to 17 hours^Label,5.

Clearance

Not Available

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.

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

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.

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

Drug	Interaction
Unlock Additional Data
(1,2,6,7-3H)Testosterone	(1,2,6,7-3H)Testosterone may increase the anticoagulant activities of Dabigatran etexilate.
(R)-warfarin	Dabigatran etexilate may increase the anticoagulant activities of (R)-warfarin.
(S)-Warfarin	Dabigatran etexilate may increase the anticoagulant activities of (S)-Warfarin.
1-Testosterone	1-Testosterone may increase the anticoagulant activities of Dabigatran etexilate.
18-methyl-19-nortestosterone	18-methyl-19-nortestosterone may increase the anticoagulant activities of Dabigatran etexilate.
3,5-Diiodotyrosine	3,5-Diiodotyrosine may increase the anticoagulant activities of Dabigatran etexilate.
4-hydroxycoumarin	Dabigatran etexilate may increase the anticoagulant activities of 4-hydroxycoumarin.
4-Hydroxytestosterone	4-Hydroxytestosterone may increase the anticoagulant activities of Dabigatran etexilate.
5beta-dihydrotestosterone	5beta-dihydrotestosterone may increase the anticoagulant activities of Dabigatran etexilate.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of bleeding and hemorrhage can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Dabigatran etexilate.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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Evidence Level
Evidence Level
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Action
Action
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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

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Dabigatran

ATC Codes

B01AE07 — Dabigatran etexilate

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

AHFS Codes

• 20:12.04.12 — Direct Thrombin Inhibitors

FDA label

Download (731 KB)

MSDS

Download (99.2 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Active Not Recruiting	Treatment	Healthy Volunteers	1
1	Completed	Not Available	Cardiovascular Disease (CVD) / Chronic Renal Failure (CRF)	1
1	Completed	Not Available	Healthy Volunteers	1
1	Completed	Basic Science	Disorders, Blood Coagulation	1
1	Completed	Basic Science	Healthy Volunteers	2
1	Completed	Other	Healthy Volunteers	2
1	Completed	Other	Prostatic Neoplasms	1
1	Completed	Treatment	Healthy Volunteers	42
1	Completed	Treatment	Hepatic Insufficiency	1
1	Completed	Treatment	Impaired Renal Function	1
1	Completed	Treatment	Interstitial Lung Disease (ILD) / Scleroderma	1
1	Completed	Treatment	Non-Alcoholic Fatty Liver Disease (NAFLD)	1
1	Completed	Treatment	Renal Insufficiency,Chronic	1
1	Completed	Treatment	Thrombotic events	1
1	Not Yet Recruiting	Treatment	Mild Alzheimer's Disease / Mild Cognitive Impairment (MCI)	1
1	Recruiting	Treatment	Acute Pancreatitis (AP)	1
1	Terminated	Treatment	Healthy Volunteers	1
2	Completed	Not Available	Venous Thromboembolism (VTE)	1
2	Completed	Prevention	Arthroplasty, Replacement, Knee / Thrombosis, Venous	1
2	Completed	Prevention	Atrial Fibrillation (AF)	1
2	Completed	Prevention	Venous Thromboembolism (VTE)	1
2	Completed	Treatment	Coronary Heart Disease (CHD)	1
2	Completed	Treatment	Minor Ischemic Stroke / Transient Ischaemic Attack (TIA)	2
2	Completed	Treatment	Venous Thromboembolism (VTE)	3
2	Not Yet Recruiting	Treatment	Anticoagulant-induced Bleeding	1
2	Terminated	Prevention	Atrial Fibrillation (AF) / Strokes	1
2	Terminated	Prevention	Heart Valve Diseases	1
2	Terminated	Prevention	Heart Valve Prosthesis / Thromboembolism	1
2	Terminated	Treatment	(Atrial Fibrillation) or (Atrial Flutter) / Atrial Fibrillation or Atrial Flutter / Thrombosis of Left Atrial Appendage	1
2	Terminated	Treatment	Bleeding / Thrombotic events	1
2	Withdrawn	Treatment	Venous Thromboembolism (VTE)	1
2, 3	Terminated	Treatment	Primary Disease	1
3	Active Not Recruiting	Prevention	Secondary Preventions / Venous Thromboembolism (VTE)	1
3	Active Not Recruiting	Treatment	Myocardial Injury After Noncardiac Surgery (MINS)	1
3	Active Not Recruiting	Treatment	Venous Thromboembolism (VTE)	1
3	Completed	Prevention	Arthroplasty, Replacement, Hip / Thromboembolism	1
3	Completed	Prevention	Arthroplasty, Replacement, Knee / Thromboembolism	2
3	Completed	Prevention	Secondary Preventions / Strokes	1
3	Completed	Prevention	Venous Thromboembolism (VTE)	2
3	Completed	Treatment	Atrial Fibrillation (AF) / Percutaneous Coronary Intervention	1
3	Completed	Treatment	Hematoma	1
3	Completed	Treatment	Thromboembolism	3
3	Not Yet Recruiting	Prevention	Stroke, Ischemic	1
3	Not Yet Recruiting	Treatment	Atrial Fibrillation (AF)	1
3	Recruiting	Prevention	Atrial Fibrillation (AF) / Atrial Flutter / Intracranial Hemorrhage, Hypertensive / Intracranial Hemorrhages / Intraventricular Hemorrhage / Microhaemorrhage / Small Vessel Cerebrovascular Disease / Subarachnoid Hemorrhage / Subdural haematoma	1
3	Recruiting	Prevention	Atrial Fibrillation (AF) / Intracerebral Hemorrhage	1
3	Recruiting	Treatment	Cerebral Venous Thrombosis	1
3	Recruiting	Treatment	Deep Vein Thrombosis / Pulmonary Embolism / Venous Thromboembolism (VTE)	1
4	Active Not Recruiting	Prevention	Atrial Fibrillation (AF) / Device Related Thrombus / Left Atrial Appendage Thrombosis / Watchman LAA Closure Device	1
4	Active Not Recruiting	Supportive Care	Atrial Fibrillation (AF) / Atrial Flutter	1
4	Completed	Basic Science	Venous Thromboembolism (VTE)	1
4	Completed	Prevention	Arthroplasty, Replacement / Moderate Renal Impairment (CrCl 30-50 mL/Min) / Prevention of Venous Thromboembolism	1
4	Completed	Prevention	Atrial Fibrillation (AF)	2
4	Completed	Treatment	Atrial Fibrillation (AF)	4
4	Completed	Treatment	Coronary Heart Disease (CHD)	1
4	Enrolling by Invitation	Treatment	Atrial Fibrillation (AF)	1
4	Not Yet Recruiting	Prevention	Atrial Fibrillation (AF) / Mitral Valve Stenosis	1
4	Not Yet Recruiting	Prevention	Atrial Fibrillation (AF) / Venous Thromboembolism (VTE)	1
4	Recruiting	Other	Atrial Fibrillation (AF) / Chronic Kidney Disease (CKD) / T2D	1
4	Recruiting	Other	Cerebral Ischemic Events / Cognition Disorders / Dementias	1
4	Recruiting	Prevention	Atrial Fibrillation (AF)	3
4	Recruiting	Treatment	Angiographically Confirmed Acute Massive Pulmonary Embolism Treated With Endovascular Mechanical Fragmentation and Thrombolytic Therapy / Dabigatran Etexilate / Pulmonary Embolism / Recurrence of DVT / Warfarin	1
4	Recruiting	Treatment	Atrial Fibrillation (AF)	2
4	Recruiting	Treatment	Atrial Fibrillation (AF) / Left Atrial Thrombosis	1
4	Recruiting	Treatment	Atrial Fibrillation (AF) / Valve Heart Disease	1
4	Recruiting	Treatment	Deep Vein Thrombosis / Pulmonary Embolism	1
4	Recruiting	Treatment	Pulmonary Embolism	1
4	Terminated	Diagnostic	Atrial Fibrillation (AF)	1
4	Terminated	Treatment	Acute Coronary Syndromes (ACS) / Atherosclerosis / Atrial Fibrillation (AF) / Coronary Heart Disease (CHD)	1
4	Unknown Status	Not Available	Anticoagulant Overdosage / Anticoagulant-induced Bleeding / Hemorrhage / Thrombotic events	1
4	Withdrawn	Treatment	Coronary Heart Disease (CHD) / Non ST Segment Elevation Myocardial Infarction (NSTEMI) / ST Elevation Myocardial Infarction (STEMI) / Stable Angina (SA) / Unstable Angina Pectoris	1
4	Withdrawn	Treatment	Thromboembolism	1
Not Available	Active Not Recruiting	Not Available	Non-valvular Atrial Fibrillation (NVAF)	1
Not Available	Active Not Recruiting	Not Available	Venous Thromboembolism (VTE)	1
Not Available	Completed	Not Available	Atrial Fibrillation (AF)	11
Not Available	Completed	Not Available	Atrial Fibrillation (AF) / Major Bleeding / Myocardial Infarction / Stroke, Ischemic / Systemic Embolization / The Mortality Rate	2
Not Available	Completed	Not Available	Atrial Fibrillation (AF) / Strokes Thrombotic	1
Not Available	Completed	Not Available	Strokes / Transient Ischaemic Attack (TIA)	1
Not Available	Completed	Not Available	Unsuspected Pulmonary Embolism	1
Not Available	Completed	Treatment	Atrial Fibrillation (AF)	1
Not Available	Completed	Treatment	Coronary Artery Disease	1
Not Available	Enrolling by Invitation	Treatment	Anticoagulant Adverse Reaction / Atrial Fibrillation (AF) / Hemorrhage / Thrombotic events	1
Not Available	Recruiting	Not Available	Atrial Fibrillation (AF) / Recurrent Venous Thromboembolism	1
Not Available	Recruiting	Not Available	Intracranial Hemorrhages	1
Not Available	Recruiting	Supportive Care	Atrial Fibrillation (AF) / Hemorrhage / Periodontal Diseases	1
Not Available	Recruiting	Treatment	Acute DVT of Lower Extremity	1
Not Available	Recruiting	Treatment	Blood Clots / Deep Vein Thrombosis / Malignancies / Pulmonary Embolism / Venous Thromboembolism (VTE)	1
Not Available	Recruiting	Treatment	Ischaemic Stroke / Stroke, Ischemic	1
Not Available	Unknown Status	Not Available	Stroke, Ischemic	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Capsule	Oral	110 mg/1
Capsule	Oral	110 mg
Capsule	Oral	150 mg
Capsule	Oral	150 mg/1
Capsule	Oral	75 mg
Capsule	Oral	75 mg/1
Capsule	Oral

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US9034822	No	2015-05-19	2031-01-20
US6087380	No	2000-07-11	2018-02-18
US7932273	No	2011-04-26	2025-09-07
US7866474	No	2011-01-11	2027-08-31
US9925174	No	2018-03-27	2023-06-14

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

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	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00kk-0981100000-78856b63936cf67ebce2
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004r-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 estersOrganic 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

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

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Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

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

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Drug created on May 03, 2010 12:25 / Updated on November 12, 2019 22:48