Dabigatran

Dabigatran
Clinical data
Trade namesPradaxa, Pradax, Prazaxa, others
Other namesBIBR-953, BIBR-1048
AHFS/Drugs.comMonograph
MedlinePlusa610024
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classDirect thrombin inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability3–7%[6]
Protein binding35%[6]
Elimination half-life12–17 hours[6]
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25N7O3
Molar mass471.521 g·mol−1
3D model (JSmol)
  • CN1C=2C(=CC(C(N(CCC(O)=O)C3=CC=CC=N3)=O)=CC2)N=C1CNC4=CC=C(C(=N)N)C=C4

  • as etexilate: CN1C=2C(=CC(C(N(CCC(OCC)=O)C3=CC=CC=N3)=O)=CC2)N=C1CNC4=CC=C(C(NC(OCCCCCC)=O)=N)C=C4
  • InChI=1S/C25H25N7O3/c1-31-20-10-7-17(25(35)32(13-11-23(33)34)21-4-2-3-12-28-21)14-19(20)30-22(31)15-29-18-8-5-16(6-9-18)24(26)27/h2-10,12,14,29H,11,13,15H2,1H3,(H3,26,27)(H,33,34)
  • Key:YBSJFWOBGCMAKL-UHFFFAOYSA-N

  • as etexilate: 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)
  • Key:KSGXQBZTULBEEQ-UHFFFAOYSA-N
 ☒NcheckY (what is this?)  (verify)

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.[6][7] Specifically it is used to prevent blood clots following hip or knee replacement and in those with a history of prior clots.[6] It is used as an alternative to warfarin and does not require monitoring by blood tests.[6] In a meta analysis of 7 different studies, there was no benefit of dabigatran over warfarin in preventing ischemic stroke; however, dabigatran were associated with a lower hazard for intracranial bleeding compared with warfarin, but also had a higher risk of gastrointestinal bleeding relative to warfarin.[8] It is taken by mouth.[6]

Common side effects include bleeding and gastritis.[6] Other side effects may include bleeding around the spine and allergic reactions such as anaphylaxis.[6] In cases of severe bleeding, it can be reversed with the antidote, idarucizumab.[6] Use is not recommended during pregnancy or breastfeeding.[6] Compared to warfarin it has fewer interactions with other medications.[9] It is a direct thrombin inhibitor.[7]

Dabigatran was approved for medical use in the United States in 2010.[6] It is on the World Health Organization's List of Essential Medicines.[10] In 2020, it was the 306th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[11] Dabigatran is available a generic medication.[12][13]

  1. ^ "Dabigatran (Pradaxa) Use During Pregnancy". Drugs.com. 27 December 2018. Archived from the original on 1 October 2020. Retrieved 16 May 2020.
  2. ^ "Pradaxa Product information". health-products.canada.ca. 22 October 2009. Retrieved 13 November 2023.
  3. ^ "Summary of Product Characteristics (SmPC)". (emc). 15 September 2022. Archived from the original on 21 April 2023. Retrieved 13 November 2023.
  4. ^ Cite error: The named reference Pradaxa FDA label was invoked but never defined (see the help page).
  5. ^ "Pradaxa EPAR". European Medicines Agency. 22 March 2023. Archived from the original on 5 June 2023. Retrieved 13 November 2023.
  6. ^ a b c d e f g h i j k l "Dabigatran Etexilate Mesylate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 27 March 2019. Retrieved 27 March 2019.
  7. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 135–137. ISBN 9780857113382.
  8. ^ Romanelli RJ, Nolting L, Dolginsky M, Kym E, Orrico KB (March 2016). "Dabigatran Versus Warfarin for Atrial Fibrillation in Real-World Clinical Practice: A Systematic Review and Meta-Analysis". Circulation: Cardiovascular Quality and Outcomes. 9 (2): 126–134. doi:10.1161/CIRCOUTCOMES.115.002369. PMID 26812933. S2CID 6840541.
  9. ^ Kiser K (2017). Oral Anticoagulation Therapy: Cases and Clinical Correlation. Springer. p. 11. ISBN 9783319546438.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ "Dabigatran - Drug Usage Statistics". ClinCalc. Archived from the original on 13 November 2022. Retrieved 7 October 2022.
  12. ^ "Office of Generic Drugs 2020 Annual Report". U.S. Food and Drug Administration (FDA). Archived from the original on 12 February 2021. Retrieved 12 February 2021.
  13. ^ "Dabigatran Etexilate Accord". European Medicines Agency. 31 May 2023. Retrieved 2 June 2023.