Dabigatran

Dabigatran etexilate
	Above: molecular structure of dabigatran etexilate Below: 3D representation of a dabigatran etexilate molecule
Clinical data
Trade names	Pradaxa, Pradax, Prazaxa, others
Other names	BIBR-953, BIBR-1048
AHFS/Drugs.com	Monograph
MedlinePlus	a610024
License data	EU EMA: by INN; US DailyMed: Dabigatran;
Pregnancy; category	AU: C;
Routes of; administration	By mouth
Drug class	Direct thrombin inhibitor
ATC code	B01AE07 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	3–7%
Protein binding	35%
Elimination half-life	12–17 hours
Identifiers
CAS Number	211914-51-1; as etexilate: 211915-06-9;
PubChem CID	216210; as etexilate: 135565674;
IUPHAR/BPS	6380; as etexilate: 6379;
DrugBank	DB14726; as etexilate: DB06695;
ChemSpider	187412; as etexilate: 4948999;
UNII	as etexilate: 2E18WX195X;
KEGG	D09707; as etexilate: D07144;
ChEBI	CHEBI:70752; as etexilate: CHEBI:70746;
ChEMBL	ChEMBL48361; as etexilate: ChEMBL539697;
PDB ligand	4CC (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID50175419 ;
Chemical and physical data
Formula	C25H25N7O3
Molar mass	471.521 g·mol−1
3D model (JSmol)	Interactive image; as etexilate: Interactive image;
	SMILES 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 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;
	(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] It is commonly used to prevent blood clots following hip or knee replacement and in those with a history of prior clots.^[6] and is used as an alternative to warfarin; it does not require monitoring by blood tests.^[6] 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.^[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 US 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]

^ "Dabigatran (Pradaxa) Use During Pregnancy". Drugs.com. American Society of Health-System Pharmacists. 27 December 2018. Archived from the original on 1 October 2020. Retrieved 16 May 2020.
^ "Pradaxa Product information". health-products.canada.ca. 22 October 2009. Retrieved 13 November 2023.
^ "Summary of Product Characteristics (SmPC)". medicines.org.uk. 15 September 2022. Archived from the original on 21 April 2023. Retrieved 13 November 2023.
^ Cite error: The named reference Pradaxa FDA label was invoked but never defined (see the help page).
^ "Pradaxa EPAR". ema.europa.eu. European Medicines Agency. 22 March 2023. Archived from the original on 5 June 2023. Retrieved 13 November 2023.
^ ^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.
^ ^a ^b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 135–137. ISBN 9780857113382.
^ 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.
^ Kiser K (2017). Oral Anticoagulation Therapy: Cases and Clinical Correlation. Springer. p. 11. ISBN 9783319546438 – via Google Books.
^ Model list of essential medicines (21st ed.). Geneva: World Health Organization. 2019. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "Dabigatran - Drug Usage Statistics". ClinCalc.com. Archived from the original on 13 November 2022. Retrieved 7 October 2022.
^ "Office of Generic Drugs 2020 Annual Report". FDA.gov. US: Food and Drug Administration. Archived from the original on 12 February 2021. Retrieved 12 February 2021.
^ "Dabigatran Etexilate Accord". ema.europa.eu. European Medicines Agency. 31 May 2023. Retrieved 2 June 2023.

[Drugs.com_pregnancy-1] "Dabigatran (Pradaxa) Use During Pregnancy". Drugs.com. American Society of Health-System Pharmacists. 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)". medicines.org.uk. 15 September 2022. Archived from the original on 21 April 2023. Retrieved 13 November 2023.

[Pradaxa_FDA_label-4] Cite error: The named reference Pradaxa FDA label was invoked but never defined (see the help page).

[Pradaxa_EPAR-5] "Pradaxa EPAR". ema.europa.eu. European Medicines Agency. 22 March 2023. Archived from the original on 5 June 2023. Retrieved 13 November 2023.

[AHFS2019-6] ^ ^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.

[BNF76-7] 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 – via Google Books.

[WHO21st-10] Model list of essential medicines (21st ed.). Geneva: World Health Organization. 2019. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[11] "Dabigatran - Drug Usage Statistics". ClinCalc.com. Archived from the original on 13 November 2022. Retrieved 7 October 2022.

[12] "Office of Generic Drugs 2020 Annual Report". FDA.gov. US: Food and Drug Administration. Archived from the original on 12 February 2021. Retrieved 12 February 2021.

[13] "Dabigatran Etexilate Accord". ema.europa.eu. European Medicines Agency. 31 May 2023. Retrieved 2 June 2023.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]