Dabigatran

Dabigatran
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;
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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.

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