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Identification
NameXimelagatran
Accession NumberDB04898
TypeSmall Molecule
GroupsApproved, Investigational, Withdrawn
DescriptionXimelagatran (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.
Structure
Thumb
Synonyms
Ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate
Exanta
Exarta
H 376-95
H 376/95
H 37695
Ximelagatranum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ExantaNot Available
ExartaNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII49HFB70472
CAS number192939-46-1
WeightAverage: 473.5652
Monoisotopic: 473.263819255
Chemical FormulaC24H35N5O5
InChI KeyInChIKey=ZXIBCJHYVWYIKI-PZJWPPBQSA-N
InChI
InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1
IUPAC Name
ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate
SMILES
CCOC(=O)CN[C@@H](C(=O)N1CC[[email protected]]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Alpha-amino acid amide
  • Phenylmethylamine
  • Benzylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Amidoxime
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Azetidine
  • Amidoxime group
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid amide
  • Amidine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of acute deep vein thrombosis.
PharmacodynamicsNot Available
Mechanism of actionXimelagatran 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.
Related Articles
AbsorptionRapidly absorbed by the small intestine with an oral bioavailability of 20%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. Ximelagatran is a prodrug, being converted in vivo to the active agent melagatran. This conversion takes place in the liver and many other tissues through dealkylation and dehydroxylation (replacing the ethyl and hydroxyl groups with hydrogen).

Route of eliminationNot Available
Half life3-5 hours
ClearanceNot Available
ToxicityHepatotoxicity (liver damage) was reported during trials.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Ximelagatran Action PathwayDrug actionSMP00279
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6065
Blood Brain Barrier-0.7499
Caco-2 permeable-0.7534
P-glycoprotein substrateSubstrate0.84
P-glycoprotein inhibitor INon-inhibitor0.755
P-glycoprotein inhibitor IINon-inhibitor0.947
Renal organic cation transporterNon-inhibitor0.7588
CYP450 2C9 substrateNon-substrate0.8632
CYP450 2D6 substrateNon-substrate0.8163
CYP450 3A4 substrateNon-substrate0.597
CYP450 1A2 substrateNon-inhibitor0.8409
CYP450 2C9 inhibitorNon-inhibitor0.7261
CYP450 2D6 inhibitorNon-inhibitor0.844
CYP450 2C19 inhibitorNon-inhibitor0.669
CYP450 3A4 inhibitorNon-inhibitor0.6775
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9157
Ames testNon AMES toxic0.6238
CarcinogenicityNon-carcinogens0.7863
BiodegradationNot ready biodegradable0.8515
Rat acute toxicity2.4109 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9654
hERG inhibition (predictor II)Inhibitor0.6003
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0845 mg/mLALOGPS
logP1.35ALOGPS
logP0.87ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.35 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity126.57 m3·mol-1ChemAxon
Polarizability52.15 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. 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:12871538 ]
  2. Weitz JI: New anticoagulants for treatment of venous thromboembolism. Circulation. 2004 Aug 31;110(9 Suppl 1):I19-26. [PubMed:15339877 ]
  3. 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:14585938 ]
  4. 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:17516699 ]
  5. 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:17636192 ]
External Links
ATC CodesB01AE05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Ximelagatran.
AbciximabAbciximab may increase the anticoagulant activities of Ximelagatran.
AbirateroneThe metabolism of Ximelagatran can be decreased when combined with Abiraterone.
AceclofenacAceclofenac may increase the anticoagulant activities of Ximelagatran.
AcenocoumarolAcenocoumarol may increase the anticoagulant activities of Ximelagatran.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Ximelagatran.
AdapaleneAdapalene may increase the anticoagulant activities of Ximelagatran.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Ximelagatran.
AllylestrenolThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Allylestrenol.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Ximelagatran.
AlprostadilAlprostadil may increase the anticoagulant activities of Ximelagatran.
AlteplaseAlteplase may increase the anticoagulant activities of Ximelagatran.
AltrenogestThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Altrenogest.
ALX-0081ALX-0081 may increase the anticoagulant activities of Ximelagatran.
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Ximelagatran.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Ximelagatran.
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Ximelagatran.
AmiodaroneThe metabolism of Ximelagatran can be decreased when combined with Amiodarone.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Ximelagatran.
AnagrelideAnagrelide may increase the anticoagulant activities of Ximelagatran.
AncrodXimelagatran may increase the anticoagulant activities of Ancrod.
AnistreplaseAnistreplase may increase the anticoagulant activities of Ximelagatran.
AntipyrineAntipyrine may increase the anticoagulant activities of Ximelagatran.
Antithrombin III humanXimelagatran may increase the anticoagulant activities of Antithrombin III human.
ApixabanApixaban may increase the anticoagulant activities of Ximelagatran.
ApremilastApremilast may increase the anticoagulant activities of Ximelagatran.
AprepitantThe metabolism of Ximelagatran can be increased when combined with Aprepitant.
AprotininThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Aprotinin.
ArdeparinArdeparin may increase the anticoagulant activities of Ximelagatran.
ArgatrobanArgatroban may increase the anticoagulant activities of Ximelagatran.
AstaxanthinAstaxanthin may increase the anticoagulant activities of Ximelagatran.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Ximelagatran.
AzapropazoneAzapropazone may increase the anticoagulant activities of Ximelagatran.
AzelastineAzelastine may increase the anticoagulant activities of Ximelagatran.
BalsalazideBalsalazide may increase the anticoagulant activities of Ximelagatran.
BatroxobinBatroxobin may increase the anticoagulant activities of Ximelagatran.
BazedoxifeneBazedoxifene may decrease the anticoagulant activities of Ximelagatran.
BecaplerminBecaplermin may increase the anticoagulant activities of Ximelagatran.
BemiparinBemiparin may increase the anticoagulant activities of Ximelagatran.
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Ximelagatran.
BeraprostBeraprost may increase the anticoagulant activities of Ximelagatran.
BivalirudinBivalirudin may increase the anticoagulant activities of Ximelagatran.
BoceprevirThe serum concentration of Ximelagatran can be decreased when it is combined with Boceprevir.
BromfenacBromfenac may increase the anticoagulant activities of Ximelagatran.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Ximelagatran.
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Ximelagatran.
CangrelorCangrelor may increase the anticoagulant activities of Ximelagatran.
CapecitabineThe metabolism of Ximelagatran can be decreased when combined with Capecitabine.
CarbamazepineThe metabolism of Ximelagatran can be increased when combined with Carbamazepine.
CarprofenCarprofen may increase the anticoagulant activities of Ximelagatran.
CastanospermineCastanospermine may increase the anticoagulant activities of Ximelagatran.
CelecoxibCelecoxib may increase the anticoagulant activities of Ximelagatran.
CeritinibThe serum concentration of Ximelagatran can be increased when it is combined with Ceritinib.
CertoparinXimelagatran may increase the anticoagulant activities of Certoparin.
ChloroquineChloroquine may increase the anticoagulant activities of Ximelagatran.
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Ximelagatran.
CholecalciferolThe metabolism of Ximelagatran can be decreased when combined with Cholecalciferol.
CilostazolCilostazol may increase the anticoagulant activities of Ximelagatran.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Ximelagatran.
Citric AcidCitric Acid may increase the anticoagulant activities of Ximelagatran.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Ximelagatran.
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Ximelagatran.
ClonixinClonixin may increase the anticoagulant activities of Ximelagatran.
ClopidogrelClopidogrel may increase the anticoagulant activities of Ximelagatran.
ClotrimazoleThe metabolism of Ximelagatran can be decreased when combined with Clotrimazole.
CollagenaseThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Collagenase.
Conjugated Equine EstrogensConjugated Equine Estrogens may decrease the anticoagulant activities of Ximelagatran.
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Ximelagatran.
CyclophosphamideThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Ximelagatran.
CyclosporineThe metabolism of Ximelagatran can be decreased when combined with Cyclosporine.
D-LimoneneD-Limonene may increase the anticoagulant activities of Ximelagatran.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Ximelagatran.
DabrafenibThe serum concentration of Ximelagatran can be decreased when it is combined with Dabrafenib.
DalteparinXimelagatran may increase the anticoagulant activities of Dalteparin.
DanaparoidXimelagatran may increase the anticoagulant activities of Danaparoid.
DasatinibDasatinib may increase the anticoagulant activities of Ximelagatran.
DeferasiroxThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Deferasirox.
DefibrotideDefibrotide may increase the anticoagulant activities of Ximelagatran.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Ximelagatran.
DelavirdineThe metabolism of Ximelagatran can be decreased when combined with Delavirdine.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Deoxycholic Acid.
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Ximelagatran.
DesirudinXimelagatran may increase the anticoagulant activities of Desirudin.
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Ximelagatran.
DesogestrelThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Desogestrel.
DextranXimelagatran may increase the anticoagulant activities of Dextran.
Dextran 40Ximelagatran may increase the anticoagulant activities of Dextran 40.
Dextran 70Ximelagatran may increase the anticoagulant activities of Dextran 70.
Dextran 75Ximelagatran may increase the anticoagulant activities of Dextran 75.
DiclofenacDiclofenac may increase the anticoagulant activities of Ximelagatran.
DicoumarolDicoumarol may increase the anticoagulant activities of Ximelagatran.
DienestrolDienestrol may decrease the anticoagulant activities of Ximelagatran.
DienogestThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Dienogest.
DiethylstilbestrolDiethylstilbestrol may decrease the anticoagulant activities of Ximelagatran.
DiflunisalDiflunisal may increase the anticoagulant activities of Ximelagatran.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Ximelagatran.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Ximelagatran.
DipyridamoleDipyridamole may increase the anticoagulant activities of Ximelagatran.
DitazoleDitazole may increase the anticoagulant activities of Ximelagatran.
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with Ximelagatran.
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Ximelagatran.
DrospirenoneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Drospirenone.
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Ximelagatran.
DroxicamDroxicam may increase the anticoagulant activities of Ximelagatran.
DydrogesteroneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Dydrogesterone.
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with Ximelagatran.
Edetic AcidEdetic Acid may increase the anticoagulant activities of Ximelagatran.
EdoxabanEdoxaban may increase the anticoagulant activities of Ximelagatran.
EfavirenzThe metabolism of Ximelagatran can be decreased when combined with Efavirenz.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Ximelagatran.
EnoxaparinEnoxaparin may increase the anticoagulant activities of Ximelagatran.
EpinastineEpinastine may increase the anticoagulant activities of Ximelagatran.
EpirizoleEpirizole may increase the anticoagulant activities of Ximelagatran.
EpoprostenolEpoprostenol may increase the anticoagulant activities of Ximelagatran.
EpoprostenolThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Epoprostenol.
EptifibatideEptifibatide may increase the anticoagulant activities of Ximelagatran.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Ximelagatran.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Ximelagatran.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Ximelagatran.
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Ximelagatran.
EstradiolEstradiol may decrease the anticoagulant activities of Ximelagatran.
EstriolEstriol may decrease the anticoagulant activities of Ximelagatran.
EstroneEstrone may decrease the anticoagulant activities of Ximelagatran.
EtanerceptEtanercept may increase the anticoagulant activities of Ximelagatran.
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Ximelagatran.
Ethyl biscoumacetateXimelagatran may increase the anticoagulant activities of Ethyl biscoumacetate.
EtodolacEtodolac may increase the anticoagulant activities of Ximelagatran.
EtofenamateEtofenamate may increase the anticoagulant activities of Ximelagatran.
EtonogestrelThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Etonogestrel.
EtoricoxibEtoricoxib may increase the anticoagulant activities of Ximelagatran.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Ximelagatran.
EtravirineThe metabolism of Ximelagatran can be decreased when combined with Etravirine.
Evening primrose oilEvening primrose oil may increase the anticoagulant activities of Ximelagatran.
exisulindexisulind may increase the anticoagulant activities of Ximelagatran.
FenbufenFenbufen may increase the anticoagulant activities of Ximelagatran.
FenoprofenFenoprofen may increase the anticoagulant activities of Ximelagatran.
FibrinolysinFibrinolysin may increase the anticoagulant activities of Ximelagatran.
FloctafenineFloctafenine may increase the anticoagulant activities of Ximelagatran.
FloxuridineThe metabolism of Ximelagatran can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Ximelagatran can be decreased when combined with Fluconazole.
FlunixinFlunixin may increase the anticoagulant activities of Ximelagatran.
FluorouracilThe metabolism of Ximelagatran can be decreased when combined with Fluorouracil.
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Ximelagatran.
FluvastatinThe metabolism of Ximelagatran can be decreased when combined with Fluvastatin.
FluvoxamineThe metabolism of Ximelagatran can be decreased when combined with Fluvoxamine.
Fondaparinux sodiumFondaparinux sodium may increase the anticoagulant activities of Ximelagatran.
FosphenytoinThe metabolism of Ximelagatran can be increased when combined with Fosphenytoin.
GarlicThe serum concentration of Ximelagatran can be decreased when it is combined with Garlic.
GemfibrozilThe metabolism of Ximelagatran can be decreased when combined with Gemfibrozil.
GenisteinGenistein may decrease the anticoagulant activities of Ximelagatran.
GestodeneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Gestodene.
HeminHemin may increase the anticoagulant activities of Ximelagatran.
HeparinHeparin may increase the anticoagulant activities of Ximelagatran.
HexestrolHexestrol may decrease the anticoagulant activities of Ximelagatran.
HirulogHirulog may increase the anticoagulant activities of Ximelagatran.
HMPL-004HMPL-004 may increase the anticoagulant activities of Ximelagatran.
Hydroxyprogesterone caproateThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Hydroxyprogesterone caproate.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Ibritumomab tiuxetan.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ximelagatran.
IbudilastIbudilast may increase the anticoagulant activities of Ximelagatran.
IbuprofenIbuprofen may increase the anticoagulant activities of Ximelagatran.
IbuproxamIbuproxam may increase the anticoagulant activities of Ximelagatran.
IcatibantIcatibant may increase the anticoagulant activities of Ximelagatran.
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Ximelagatran.
IfenprodilIfenprodil may increase the anticoagulant activities of Ximelagatran.
IloprostIloprost may increase the anticoagulant activities of Ximelagatran.
IloprostThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Iloprost.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Ximelagatran.
IndinavirThe metabolism of Ximelagatran can be decreased when combined with Indinavir.
IndomethacinIndomethacin may increase the anticoagulant activities of Ximelagatran.
IndoprofenIndoprofen may increase the anticoagulant activities of Ximelagatran.
IrbesartanThe metabolism of Ximelagatran can be decreased when combined with Irbesartan.
IsoxicamIsoxicam may increase the anticoagulant activities of Ximelagatran.
KebuzoneKebuzone may increase the anticoagulant activities of Ximelagatran.
KetoconazoleThe metabolism of Ximelagatran can be decreased when combined with Ketoconazole.
KetoprofenKetoprofen may increase the anticoagulant activities of Ximelagatran.
KetorolacKetorolac may increase the anticoagulant activities of Ximelagatran.
LeflunomideLeflunomide may increase the anticoagulant activities of Ximelagatran.
LepirudinLepirudin may increase the anticoagulant activities of Ximelagatran.
LevonorgestrelThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Levonorgestrel.
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Ximelagatran.
LornoxicamLornoxicam may increase the anticoagulant activities of Ximelagatran.
LosartanThe metabolism of Ximelagatran can be decreased when combined with Losartan.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Ximelagatran.
LovastatinThe metabolism of Ximelagatran can be decreased when combined with Lovastatin.
LoxoprofenLoxoprofen may increase the anticoagulant activities of Ximelagatran.
LumacaftorThe serum concentration of Ximelagatran can be decreased when it is combined with Lumacaftor.
LumiracoxibLumiracoxib may increase the anticoagulant activities of Ximelagatran.
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Ximelagatran.
MasoprocolMasoprocol may increase the anticoagulant activities of Ximelagatran.
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Ximelagatran.
MedrogestoneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Medrogestone.
Medroxyprogesterone acetateThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Medroxyprogesterone acetate.
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Ximelagatran.
Megestrol acetateThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Megestrol acetate.
MeloxicamMeloxicam may increase the anticoagulant activities of Ximelagatran.
MesalazineMesalazine may increase the anticoagulant activities of Ximelagatran.
MestranolMestranol may decrease the anticoagulant activities of Ximelagatran.
MetamizoleMetamizole may increase the anticoagulant activities of Ximelagatran.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Ximelagatran.
MifepristoneThe serum concentration of Ximelagatran can be increased when it is combined with Mifepristone.
MilrinoneMilrinone may increase the anticoagulant activities of Ximelagatran.
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Ximelagatran.
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Ximelagatran.
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Ximelagatran.
NabumetoneNabumetone may increase the anticoagulant activities of Ximelagatran.
NadroparinXimelagatran may increase the anticoagulant activities of Nadroparin.
NaftifineNaftifine may increase the anticoagulant activities of Ximelagatran.
NaproxenNaproxen may increase the anticoagulant activities of Ximelagatran.
NCX 4016NCX 4016 may increase the anticoagulant activities of Ximelagatran.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Ximelagatran.
NepafenacNepafenac may increase the anticoagulant activities of Ximelagatran.
NicardipineThe metabolism of Ximelagatran can be decreased when combined with Nicardipine.
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Ximelagatran.
NimesulideNimesulide may increase the anticoagulant activities of Ximelagatran.
NintedanibThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Nintedanib.
NorethisteroneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Norethisterone.
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Ximelagatran.
ObinutuzumabThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Obinutuzumab.
OlopatadineOlopatadine may increase the anticoagulant activities of Ximelagatran.
OlsalazineOlsalazine may increase the anticoagulant activities of Ximelagatran.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Omacetaxine mepesuccinate.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Ximelagatran.
OmeprazoleThe metabolism of Ximelagatran can be decreased when combined with Omeprazole.
OrgoteinOrgotein may increase the anticoagulant activities of Ximelagatran.
OtamixabanXimelagatran may increase the anticoagulant activities of Otamixaban.
OxaprozinOxaprozin may increase the anticoagulant activities of Ximelagatran.
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Ximelagatran.
ParecoxibParecoxib may increase the anticoagulant activities of Ximelagatran.
ParnaparinParnaparin may increase the anticoagulant activities of Ximelagatran.
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Ximelagatran.
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Ximelagatran.
PethidineThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Pethidine.
PhenindionePhenindione may increase the anticoagulant activities of Ximelagatran.
PhenobarbitalThe metabolism of Ximelagatran can be increased when combined with Phenobarbital.
PhenprocoumonPhenprocoumon may increase the anticoagulant activities of Ximelagatran.
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Ximelagatran.
PhenytoinThe metabolism of Ximelagatran can be increased when combined with Phenytoin.
PimecrolimusPimecrolimus may increase the anticoagulant activities of Ximelagatran.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Ximelagatran.
PirfenidonePirfenidone may increase the anticoagulant activities of Ximelagatran.
PiroxicamPiroxicam may increase the anticoagulant activities of Ximelagatran.
PlasminPlasmin may increase the anticoagulant activities of Ximelagatran.
Polyestradiol phosphatePolyestradiol phosphate may decrease the anticoagulant activities of Ximelagatran.
PrasugrelPrasugrel may increase the anticoagulant activities of Ximelagatran.
PrimidoneThe metabolism of Ximelagatran can be increased when combined with Primidone.
ProgesteroneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Progesterone.
PropacetamolPropacetamol may increase the anticoagulant activities of Ximelagatran.
Protein CXimelagatran may increase the anticoagulant activities of Protein C.
ProtocatechualdehydeXimelagatran may increase the anticoagulant activities of Protocatechualdehyde.
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Ximelagatran.
PTC299PTC299 may increase the anticoagulant activities of Ximelagatran.
PyrimethamineThe metabolism of Ximelagatran can be decreased when combined with Pyrimethamine.
QuinestrolQuinestrol may decrease the anticoagulant activities of Ximelagatran.
QuinineThe metabolism of Ximelagatran can be decreased when combined with Quinine.
ResveratrolResveratrol may increase the anticoagulant activities of Ximelagatran.
ReteplaseReteplase may increase the anticoagulant activities of Ximelagatran.
ReviparinXimelagatran may increase the anticoagulant activities of Reviparin.
RidogrelRidogrel may increase the anticoagulant activities of Ximelagatran.
RifampicinThe metabolism of Ximelagatran can be increased when combined with Rifampicin.
RifapentineThe metabolism of Ximelagatran can be increased when combined with Rifapentine.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Ximelagatran.
RivaroxabanXimelagatran may increase the anticoagulant activities of Rivaroxaban.
RofecoxibRofecoxib may increase the anticoagulant activities of Ximelagatran.
RosiglitazoneRosiglitazone may increase the anticoagulant activities of Ximelagatran.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Ximelagatran.
SalicylamideSalicylamide may increase the anticoagulant activities of Ximelagatran.
Salicylic acidSalicylic acid may increase the anticoagulant activities of Ximelagatran.
SalsalateSalsalate may increase the anticoagulant activities of Ximelagatran.
SCH-530348SCH-530348 may increase the anticoagulant activities of Ximelagatran.
SecobarbitalThe metabolism of Ximelagatran can be increased when combined with Secobarbital.
SelexipagSelexipag may increase the anticoagulant activities of Ximelagatran.
SeratrodastSeratrodast may increase the anticoagulant activities of Ximelagatran.
SevofluraneSevoflurane may increase the anticoagulant activities of Ximelagatran.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Ximelagatran.
SildenafilThe metabolism of Ximelagatran can be decreased when combined with Sildenafil.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Ximelagatran.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Ximelagatran.
SorafenibThe metabolism of Ximelagatran can be decreased when combined with Sorafenib.
SRT501SRT501 may increase the anticoagulant activities of Ximelagatran.
St. John's WortThe metabolism of Ximelagatran can be increased when combined with St. John's Wort.
StreptokinaseStreptokinase may increase the anticoagulant activities of Ximelagatran.
SugammadexSugammadex may increase the anticoagulant activities of Ximelagatran.
SulfadiazineThe metabolism of Ximelagatran can be decreased when combined with Sulfadiazine.
SulfamethoxazoleThe metabolism of Ximelagatran can be decreased when combined with Sulfamethoxazole.
SulfasalazineSulfasalazine may increase the anticoagulant activities of Ximelagatran.
SulfisoxazoleThe metabolism of Ximelagatran can be decreased when combined with Sulfisoxazole.
SulindacSulindac may increase the anticoagulant activities of Ximelagatran.
SulodexideXimelagatran may increase the anticoagulant activities of Sulodexide.
SuprofenSuprofen may increase the anticoagulant activities of Ximelagatran.
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Ximelagatran.
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Ximelagatran.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Ximelagatran.
TemsirolimusThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Temsirolimus.
TenecteplaseTenecteplase may increase the anticoagulant activities of Ximelagatran.
TenoxicamTenoxicam may increase the anticoagulant activities of Ximelagatran.
TepoxalinTepoxalin may increase the anticoagulant activities of Ximelagatran.
TeriflunomideTeriflunomide may increase the anticoagulant activities of Ximelagatran.
TesmilifeneTesmilifene may increase the anticoagulant activities of Ximelagatran.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Ximelagatran.
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Ximelagatran.
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Ximelagatran.
TiboloneTibolone may increase the anticoagulant activities of Ximelagatran.
TicagrelorTicagrelor may increase the anticoagulant activities of Ximelagatran.
TiclopidineTiclopidine may increase the anticoagulant activities of Ximelagatran.
TinzaparinTinzaparin may increase the anticoagulant activities of Ximelagatran.
TipranavirThe serum concentration of Ximelagatran can be decreased when it is combined with Tipranavir.
TirofibanTirofiban may increase the anticoagulant activities of Ximelagatran.
TolbutamideThe metabolism of Ximelagatran can be decreased when combined with Tolbutamide.
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Ximelagatran.
TolmetinTolmetin may increase the anticoagulant activities of Ximelagatran.
TositumomabThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Tositumomab.
TranilastTranilast may increase the anticoagulant activities of Ximelagatran.
TrapidilTrapidil may increase the anticoagulant activities of Ximelagatran.
TreprostinilTreprostinil may increase the anticoagulant activities of Ximelagatran.
TreprostinilThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Treprostinil.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Ximelagatran.
TriflusalTriflusal may increase the anticoagulant activities of Ximelagatran.
TrimethoprimThe metabolism of Ximelagatran can be decreased when combined with Trimethoprim.
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Ximelagatran.
Trisalicylate-cholineTrisalicylate-choline may increase the anticoagulant activities of Ximelagatran.
UrokinaseUrokinase may increase the anticoagulant activities of Ximelagatran.
ValdecoxibValdecoxib may increase the anticoagulant activities of Ximelagatran.
Valproic AcidThe metabolism of Ximelagatran can be decreased when combined with Valproic Acid.
ValsartanThe metabolism of Ximelagatran can be decreased when combined with Valsartan.
Vitamin EVitamin E may increase the anticoagulant activities of Ximelagatran.
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ximelagatran.
VoriconazoleThe metabolism of Ximelagatran can be decreased when combined with Voriconazole.
WarfarinWarfarin may increase the anticoagulant activities of Ximelagatran.
ZafirlukastThe metabolism of Ximelagatran can be decreased when combined with Zafirlukast.
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Ximelagatran.
ZeranolZeranol may decrease the anticoagulant activities of Ximelagatran.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Ximelagatran.
ZileutonZileuton may increase the anticoagulant activities of Ximelagatran.
ZomepiracZomepirac may increase the anticoagulant activities of Ximelagatran.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Thrombospondin receptor activity
Specific Function:
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
Molecular Weight:
70036.295 Da
References
  1. Testa L, Bhindi R, Agostoni P, Abbate A, Zoccai GG, van Gaal WJ: The direct thrombin inhibitor ximelagatran/melagatran: a systematic review on clinical applications and an evidence based assessment of risk benefit profile. Expert Opin Drug Saf. 2007 Jul;6(4):397-406. [PubMed:17688383 ]
  2. Ho SJ, Brighton TA: Ximelagatran: direct thrombin inhibitor. Vasc Health Risk Manag. 2006;2(1):49-58. [PubMed:17319469 ]
  3. 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:17516699 ]
  4. Ersdal E, Schutzer KM, Lonnerstedt C, Ohlsson L, Wall U, Eriksson UG: No influence of food on the pharmacokinetics, pharmacodynamics or tolerability of the 24mg and 36mg oral tablet formulations of ximelagatran. Clin Drug Investig. 2005;25(7):425-33. [PubMed:17532684 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on October 21, 2007 16:23 / Updated on August 17, 2016 12:24