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Namespace Prefixes

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Statements

Subject Item
n2:DB04898
rdf:type
n3:Drug
n3:description
Ximelagatran (Exanta® or Exarta®, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, its manufacturer AstraZeneca announced that it would not attempt to market ximelagatran after reports of hepatotoxicity (liver damage) during trials, and to discontinue its distribution in countries where the drug had been approved.
n3:generalReferences
# Eriksson H, Wahlander K, Gustafsson D, Welin LT, Frison L, Schulman S: A randomized, controlled, dose-guiding study of the oral direct thrombin inhibitor ximelagatran compared with standard therapy for the treatment of acute deep vein thrombosis: THRIVE I. J Thromb Haemost. 2003 Jan;1(1):41-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12871538 # Weitz JI: New anticoagulants for treatment of venous thromboembolism. Circulation. 2004 Aug 31;110(9 Suppl 1):I19-26. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15339877 # Francis CW, Berkowitz SD, Comp PC, Lieberman JR, Ginsberg JS, Paiement G, Peters GR, Roth AW, McElhattan J, Colwell CW Jr: Comparison of ximelagatran with warfarin for the prevention of venous thromboembolism after total knee replacement. N Engl J Med. 2003 Oct 30;349(18):1703-12. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/14585938 # Bergqvist D, Solhaug JH, Holmdahl L, Eriksson UG, Andersson M, Boberg B, Ogren M: Pharmacokinetics, preliminary efficacy and safety of subcutaneous melagatran and oral ximelagatran : a multicentre study of thromboprophylaxis in elective abdominal surgery. Clin Drug Investig. 2004;24(3):127-36. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17516699 # Koscielny J, Kiesewetter H, Jorg I, Harenberg J: Ximelagatran for treatment and prophylaxis of recurrent events in deep vein thrombosis. Clin Appl Thromb Hemost. 2007 Jul;13(3):299-307. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17636192
n3:group
approved withdrawn investigational
n3:halfLife
3-5 hours
n3:indication
For the treatment of acute deep vein thrombosis.
owl:sameAs
n8:DB04898 n9:DB04898
dcterms:title
Ximelagatran
adms:identifier
n11:7848559 n12:DB04898 n15:Ximelagatran n16:PA161748474 n18:9574101 n19:46509040
n3:mechanismOfAction
Ximelagatran was the first member of the drug class of direct thrombin inhibitors that can be taken orally. It acts solely by inhibiting the actions of thrombin. Ximelagatran is a prodrug, being converted in vivo to the active agent melagatran.
n3:synonym
H 376/95 Ximelagatranum Exanta H 376-95 Exarta H 37695 Ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate
n3:toxicity
Hepatotoxicity (liver damage) was reported during trials.
n5:hasConcept
n6:M0388208
n3:IUPAC-Name
n4:271B5E15-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5E1B-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5E1A-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5E17-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5E18-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5E19-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5E13-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5E11-363D-11E5-9242-09173F13E4C5 n4:271B5E14-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5E12-363D-11E5-9242-09173F13E4C5
n13:hasATCCode
n14:B01AE05
n3:H-Bond-Acceptor-Count
n4:271B5E21-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5E22-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5E1C-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5E1D-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5E1F-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5E1E-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5E20-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapidly absorbed by the small intestine with an oral bioavailability of 20%.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
192939-46-1
n3:category
n3:Bioavailability
n4:271B5E27-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5E29-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5E2A-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5E26-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5E25-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5E28-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5E16-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5E23-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5E24-363D-11E5-9242-09173F13E4C5