Structure via PubChem · Public domain (PubChem)
dabigatran
Sign in to saveAlso known as Pradaxa
Dabigatran, sold under the brand name Pradaxa among others, is an anticoagulant used to treat and prevent blood clots and to prevent stroke in people with atrial fibrillation. It is commonly used to prevent blood clots following hip or knee replacement and in those with a history of prior clots. and is used as an alternative to warfarin; it does not require monitoring by blood tests. In a meta-analysis of seven different studies, there was no benefit of dabigatran over warfarin in preventing ischemic stroke; however, dabigatran was associated with a lower hazard for intracranial bleeding compa
Key facts
- Drug.width
- 275
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 457472984
- Drug.drug_name
- Dabigatran etexilate
- Drug.image
- Dabigatran etexilate.svg
- Drug.image_class
- skin-invert-image
- Drug.caption
- Above: molecular structure of dabigatran etexilate Below: 3D representation of a dabigatran etexilate molecule
- Drug.image2
- Dabigatran 3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Pradaxa, Pradax, Prazaxa, others
- Drug.MedlinePlus
- a610024
- Drug.licence_EU
- yes
- Drug.DailyMedID
- Dabigatran
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth
- Drug.class
- Direct thrombin inhibitor
- Drug.ATC_prefix
- B01
via Wikipedia infobox
Chemical data
- Formula
- C25H25N7O3
- Molecular weight
- 471.5 g/mol
- IUPAC name
- 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid
- SMILES
- CN1C2=C(C=C(C=C2)C(=O)N(CCC(=O)O)C3=CC=CC=N3)N=C1CNC4=CC=C(C=C4)C(=N)N
- InChIKey
- YBSJFWOBGCMAKL-UHFFFAOYSA-N
- XLogP
- 1.7
- Polar surface area
- 150 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
7,397 papers- Dabigatran Etexilate: A Review in Pediatric Venous Thromboembolism.Paediatric drugs · 2022
- Dabigatran - Metabolism, Pharmacologic Properties and Drug Interactions.Current drug metabolism · 2017
- [Dabigatran-induced oesophagitis].Nederlands tijdschrift voor geneeskunde · 2019
- Dabigatran-induced esophagitis.Cleveland Clinic journal of medicine · 2019
- Dabigatran Etexilate: A Review in Nonvalvular Atrial Fibrillation.Drugs · 2017
via PubMed
Wikidata facts
- Mass
- 471.202
Show 5 more facts
- chemical formula
- C₂₅H₂₅N₇O₃
- canonical SMILES
- CN1C2=C(C=C(C=C2)C(=O)N(CCC(=O)O)C3=CC=CC=N3)N=C1CNC4=CC=C(C=C4)C(=N)N
- Commons category
- Dabigatran
- World Health Organisation international non-proprietary name
- dabigatran
- isomeric SMILES
- [H]/N=C(\c1ccc(cc1)NCc2nc3cc(ccc3n2C)C(=O)N(CCC(=O)O)c4ccccn4)/N
via Wikidata · CC0
~12 min read
Article
8 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- References
Dabigatran, sold under the brand name Pradaxa among others, is an anticoagulant used to treat and prevent blood clots and to prevent stroke in people with atrial fibrillation. It is commonly used to prevent blood clots following hip or knee replacement and in those with a history of prior clots. and is used as an alternative to warfarin; it does not require monitoring by blood tests. In a meta-analysis of seven different studies, there was no benefit of dabigatran over warfarin in preventing ischemic stroke; however, dabigatran was associated with a lower hazard for intracranial bleeding compared with warfarin, but also had a higher risk of gastrointestinal bleeding. It is taken by mouth.
Common side effects include bleeding and gastritis. Other side effects may include bleeding around the spine and allergic reactions such as anaphylaxis. In cases of severe bleeding, it can be reversed with the antidote, idarucizumab. Use is not recommended during pregnancy or breastfeeding. Compared to warfarin it has fewer interactions with other medications. It is a direct thrombin inhibitor.