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Encyclopedia > Dabigatran
Dabigatran chemical structure
Dabigatran
Systematic (IUPAC) name
ethyl 3-(((2-(((4-((((hexyloxy)carbonyl)amino)
iminomethyl)phenyl)amino)methyl)-
1-methyl-1H-benzimidazol-5-yl)carbonyl)
(pyridin-2-yl)amino)propanoate
Identifiers
CAS number 211915-06-9
211914-51-1
ATC code  ?
PubChem 6445226
Chemical data
Formula C34H41N7O5 
Mol. weight 627.734 (471.511 without etexilate)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules . ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance transparent (gas) very pale blue (liquid) Atomic mass 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms anggjgjhnd cell (b). ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ...

Legal status
Dependence Liability unknown
Routes oral

Dabigatran is an anticoagulant from the class of the direct thrombin inhibitors. It is being studied for various clinical indications, for some of which it may replace warfarin as the preferred anticoagulant. It is orally administered as the prodrug dabigatran etexilate (Rendix®). It was developed by pharmaceutical company Boehringer-Ingelheim. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An anticoagulant is a substance that prevents coagulation; that is, it stops blood from clotting. ... Warfarin (also known under the brand names of Coumadin®, Jantoven®, Marevan®, and Waran®) is an anticoagulant medication that is administered orally or, very rarely, by injection. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... Boehringer Ingelheim is a global pharmaceutical company based in Germany. ...

Contents


Development

Dabigatran (then compound BIBR 953) was discovered from a panel of chemicals with similar structure to benzamidine-based thrombin inhibitor α-NAPAP (N-alpha-(2-naphthylsulfonylglycyl)-4-amidinophenylalanine piperidide), which had been known since the 1980s as a powerful inhibitor of various serine proteases, specifically thrombin but also trypsin. Addition of a hydrophobic side chain led to the orally absorbed prodrug BIBR 1048 (dabigatran etexilate).[1] In biochemistry, serine proteases or serine endopeptidases (newer name) are a class of peptidases (enzymes that cleave peptide bonds in proteins) that are characterised by the presence of a serine residue in the active center of the enzyme. ... Trypsin(EC 3. ...


Dosing

A 2004 study showed a good safety profile at doses between 12.5 and 300 mg twice daily.[2]


In a phase II study comparing dabigatran with enoxaparin showed increased efficacy in preventing thrombosis in patients undergoing orthopedic surgery, but a possible increased bleeding risk in patients receiving higher doses of dabigatran.[3] Enoxaparin is a low molecular weight heparin manufactured by Sanofi-Aventis. ...


Absorption is unrelated to food but may be decreased with co-administration of proton pump inhibitors.[4] Proton pump inhibitors are a group of drugs whose main action is pronounced and long-lasting reduction of gastric acid production. ...


References

  1. ^ Hauel NH, Nar H, Priepke H, Ries U, Stassen JM, Wienen W. Structure-based design of novel potent nonpeptide thrombin inhibitors. J Med Chem 2002;45:1757-66. PMID 11960487.
  2. ^ Eriksson BI, Dahl OE, Ahnfelt L, Kalebo P, Stangier J, Nehmiz G, Hermansson K, Kohlbrenner V. Dose escalating safety study of a new oral direct thrombin inhibitor, dabigatran etexilate, in patients undergoing total hip replacement: BISTRO I. J Thromb Haemost 2004;2:1573-80. PMID 15333033.
  3. ^ Eriksson BI, Dahl OE, Buller HR, Hettiarachchi R, Rosencher N, Bravo ML, Ahnfelt L, Piovella F, Stangier J, Kalebo P, Reilly P; BISTRO II Study Group. A new oral direct thrombin inhibitor, dabigatran etexilate, compared with enoxaparin for prevention of thromboembolic events following total hip or knee replacement: the BISTRO II randomized trial. J Thromb Haemost 2005;3:103-11. PMID 15634273.
  4. ^ Stangier J, Eriksson BI, Dahl OE, Ahnfelt L, Nehmiz G, Stahle H, Rathgen K, Svard R. Pharmacokinetic profile of the oral direct thrombin inhibitor dabigatran etexilate in healthy volunteers and patients undergoing total hip replacement. J Clin Pharmacol 2005;45:555-63. PMID 15831779.

External links

  • Official site ("under construction")
  • Warfarinfo page on dabigatran


Antithrombotics (thrombolytics, anticoagulants, and antiplatelet drugs) (B01) edit
Vitamin K antagonists:

Acenocoumarol, Clorindione, Dicumarol (Dicoumarol}, Diphenadione, Ethyl biscoumacetate, Phenprocoumon, Phenindione, Tioclomarol, Warfarin Thrombolytic drugs are used in medicine to dissolve blood clots in a procedure termed thrombolysis. ... An anticoagulant is a substance that prevents coagulation; that is, it stops blood from clotting. ... An antiplatelet drug is a member of a class of pharmaceuticals that decreases platelet aggregation and inhibits thrombus formation. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Acenocoumarol is a anticoagulant that functions as a vitamin K antagonist (like warfarin). ... Warfarin (also known under the brand names of Coumadin®, Jantoven®, Marevan®, and Waran®) is an anticoagulant medication that is administered orally or, very rarely, by injection. ...

Heparin group (Platelet
aggregation inhibitors):

Antithrombin III, Bemiparin, Dalteparin, Danaparoid, Enoxaparin, Heparin, Nadroparin, Parnaparin, Reviparin, Sulodexide, Tinzaparin Antithrombin is a small molecule that inactivates several enzymes of the coagulation system. ... Dalteparin is a low molecular weight heparin. ... Danaparoid sodium (Orgaran®) is an anticoagulant that works by inhibiting thrombin. ... Enoxaparin is a low molecular weight heparin manufactured by Sanofi-Aventis. ... Heparin as a drug is used as an injectable anticoagulant. ... In medicine, low molecular weight heparin (LMWH) is a class of medication used as an anticoagulant in diseases that feature thrombosis, as well as for prophylaxis in situations that lead to a high risk of thrombosis. ...

Other Platelet
aggregation inhibitors:

Abciximab, Acetylsalicylic acid (Aspirin), Aloxiprin, Beraprost, Ditazole, Carbasalate calcium, Cloricromen, Clopidogrel, Dipyridamole, Epoprostenol, Eptifibatide, Indobufen, Iloprost, Picotamide, Prasugrel, Ticlopidine, Tirofiban, Treprostinil, Triflusal Abciximab (previously known as c7E3 Fab), distributed by Eli Lilly under the trade name ReoPro®, is a platelet aggregation inhibitor mainly used during and after coronary artery procedures like angioplasty to prevent platelets from sticking together and causing thrombus (blood clot) formation within the coronary artery. ... A very old bottle of Aspirin Aspirin or acetylsalicylic acid is a drug in the family of salicylates, often used as an analgesic (against minor pains and aches), antipyretic (against fever), and anti-inflammatory. ... Clopidogrel (IPA: ) is a potent oral antiplatelet agent often used in the treatment of coronary artery disease, peripheral vascular disease, and cerebrovascular disease. ... Dipyridamole is a drug that inhibits platelet aggregation and causes vasodilation. ... Prostacyclin is a member of the family of lipid molecules known as eicosanoids. ... Eptifibatide (Integrilin®, Millennium Pharmaceuticals) is a anti-coagulant that selectively blocks the platelet glycoprotein IIb/IIIa receptor. ... iloprost, an inhalation solution, is sold under the name Ventavis® and is used to treat pulmonary arterial hypertension (PAH). ... Prasugrel is a novel platelet inhibitor developed by Sankyo and produced by Ube and currently under clinical development in cooperation with Eli Lilly for acute coronary syndromes planned for PCI. Categories: Biochemistry stubs | Pharmacology stubs ... Ticlopidine is a drug used for its antiplatelet action. ... // Basic Chemical and Pharmacological Information Tirofiban is a synthetic, nonpeptide inhibitor acting at glycoprotein-(GP)-receptors, type IIb/IIIa, in human thrombocytes. ...

Enzymes:

Alteplase, Ancrod, Anistreplase, Brinase, Drotrecogin alfa, Fibrinolysin, Protein C, Reteplase, Saruplase, Streptokinase, Tenecteplase, Urokinase In blood coagulation, tissue plasminogen activator (tPA) is an enzyme (EC 3. ... // Basic Chemical, Pharmacological, and Marketing Information Ancrod (also known under its former brand name Arwin® and recently Viprinex®) is an anticoagulant with a triple mode of action. ... Anistreplase is a thrombolytic drug. ... // Basic Chemical, Pharmacological and Marketing Data Drotrecogin alpha (activated) is a recombinant form of human activated protein C that has antithrombotic, antiinflammatory, and profibrinolytic properties. ... Protein C is a major physiological anticoagulant. ... Reteplase (Retavase®) is a thrombolytic drug, used to treat heart attacks by breaking up the clots that cause them. ... Streptokinase is an extracellular metallo-enzyme produced by beta-haemolytic streptococcus and is used as an effective and cheap clot-dissolving medication in some cases of myocardial infarction (heart attack) and pulmonary embolism. ... Urokinase, also called urokinase-type Plasminogen Activator (uPA) is an enzyme (EC 3. ...

Direct thrombin inhibitors:

Argatroban, Bivalirudin, Desirudin, Lepirudin, Melagatran, Ximelagatran Argatroban is a small molecule direct thrombin inhibitor. ... Basic Chemical and Pharmacological Properties Bivalirudin is an anticoagulant and acts as direct thrombin antagonist. ... Ximelagatran (Exanta®, H 376/95) is an anticoagulant that has been investigated extensively but is awaiting approval by the Food and Drug Administration (FDA). ... Ximelagatran (Exanta®, H 376/95) is an anticoagulant that has been investigated extensively but is awaiting approval by the Food and Drug Administration (FDA). ...

Other antithrombotics:

Dabigatran, Defibrotide, Dermatan sulfate, Fondaparinux, Rivaroxaban Dermatan sulfate is a glycosaminoglycan, formerly called a mucopolysaccharide, found mostly in skin, but also in blood vessels, heart valves, tendons, and lungs. ... Fondaparinux (Arixtra) is a medication that is an anticoagulant. ... Rivaroxaban (also known as BAY 59-7939) is an oral anticoagulant under development by Bayer. ...

Non-medicinal:

Citrate, EDTA, Oxalate An anticoagulant is a substance that prevents coagulation; that is, it stops blood from clotting. ... Chemical strucutre of citric acid. ... EDTA is the chemical compound ethylenediaminetetraacetic acid. ... The oxalate (also ethanedioate) ion is (COO)22− (oxalic acid minus two hydrogen ions). ...



 
 

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