Identification

Name
Ximelagatran
Accession Number
DB04898
Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
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.

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 37695
  • Ximelagatranum
External IDs
H 376/95
International/Other Brands
Exanta / Exarta
Categories
UNII
49HFB70472
CAS number
192939-46-1
Weight
Average: 473.5652
Monoisotopic: 473.263819255
Chemical Formula
C24H35N5O5
InChI Key
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[[email protected]@H](C(=O)N1CC[[email protected]]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1

Pharmacology

Indication

For the treatment of acute deep vein thrombosis.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

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.

TargetActionsOrganism
AProthrombin
inhibitor
Human
Absorption

Rapidly absorbed by the small intestine with an oral bioavailability of 20%.

Volume of distribution
Not Available
Protein binding
Not 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 elimination
Not Available
Half life

3-5 hours

Clearance
Not Available
Toxicity

Hepatotoxicity (liver damage) was reported during trials.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Ximelagatran Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Ximelagatran.Approved, Investigational
AbciximabAbciximab may increase the anticoagulant activities of Ximelagatran.Approved
AbirateroneThe metabolism of Ximelagatran can be decreased when combined with Abiraterone.Approved
AceclofenacAceclofenac may increase the anticoagulant activities of Ximelagatran.Approved
AcemetacinAcemetacin may increase the anticoagulant activities of Ximelagatran.Approved
AcenocoumarolAcenocoumarol may increase the anticoagulant activities of Ximelagatran.Approved
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
AdapaleneAdapalene may increase the anticoagulant activities of Ximelagatran.Approved
AlclofenacAlclofenac may increase the anticoagulant activities of Ximelagatran.Approved, Withdrawn
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Ximelagatran.Approved, Investigational
AllylestrenolThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Allylestrenol.Approved
AlminoprofenAlminoprofen may increase the anticoagulant activities of Ximelagatran.Experimental
AloxiprinAloxiprin may increase the anticoagulant activities of Ximelagatran.Experimental
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Ximelagatran.Approved, Illicit, Investigational
AlprostadilAlprostadil may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
AlteplaseAlteplase may increase the anticoagulant activities of Ximelagatran.Approved
AltrenogestThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Altrenogest.Vet Approved
ALX-0081ALX-0081 may increase the anticoagulant activities of Ximelagatran.Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be decreased when it is combined with Ximelagatran.Experimental
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Ximelagatran.Illicit, Withdrawn
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Ximelagatran.Approved
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Ximelagatran.Approved
AmiodaroneThe metabolism of Ximelagatran can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Ximelagatran.Approved
AnagrelideAnagrelide may increase the anticoagulant activities of Ximelagatran.Approved
AncrodXimelagatran may increase the anticoagulant activities of Ancrod.Investigational
AndrographolideAndrographolide may increase the anticoagulant activities of Ximelagatran.Investigational
AnisodamineAnisodamine may increase the anticoagulant activities of Ximelagatran.Investigational
AnistreplaseAnistreplase may increase the anticoagulant activities of Ximelagatran.Approved
AntipyrineAntipyrine may increase the anticoagulant activities of Ximelagatran.Approved
Antithrombin III humanXimelagatran may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanApixaban may increase the anticoagulant activities of Ximelagatran.Approved
ApocyninApocynin may increase the anticoagulant activities of Ximelagatran.Investigational
ApremilastApremilast may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
AprepitantThe metabolism of Ximelagatran can be increased when combined with Aprepitant.Approved, Investigational
AprotininThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Aprotinin.Approved, Withdrawn
ArdeparinArdeparin may increase the anticoagulant activities of Ximelagatran.Approved, Withdrawn
ArgatrobanArgatroban may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
AstaxanthinAstaxanthin may increase the anticoagulant activities of Ximelagatran.Investigational
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Ximelagatran.Approved
AzapropazoneAzapropazone may increase the anticoagulant activities of Ximelagatran.Withdrawn
AzelastineAzelastine may increase the anticoagulant activities of Ximelagatran.Approved
BalsalazideBalsalazide may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
BatroxobinBatroxobin may increase the anticoagulant activities of Ximelagatran.Experimental
BecaplerminBecaplermin may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
BemiparinBemiparin may increase the anticoagulant activities of Ximelagatran.Approved
BendazacBendazac may increase the anticoagulant activities of Ximelagatran.Experimental
BenorilateBenorilate may increase the anticoagulant activities of Ximelagatran.Experimental
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Ximelagatran.Withdrawn
BeraprostBeraprost may increase the anticoagulant activities of Ximelagatran.Investigational
BevoniumBevonium may increase the anticoagulant activities of Ximelagatran.Experimental
BivalirudinBivalirudin may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
BoceprevirThe serum concentration of Ximelagatran can be decreased when it is combined with Boceprevir.Withdrawn
BrinaseBrinase may increase the anticoagulant activities of Ximelagatran.Experimental
BromfenacBromfenac may increase the anticoagulant activities of Ximelagatran.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Ximelagatran.Approved, Investigational
BucillamineBucillamine may increase the anticoagulant activities of Ximelagatran.Investigational
BufexamacBufexamac may increase the anticoagulant activities of Ximelagatran.Experimental
BuflomedilBuflomedil may increase the anticoagulant activities of Ximelagatran.Experimental
BumadizoneBumadizone may increase the anticoagulant activities of Ximelagatran.Experimental
ButylphthalideButylphthalide may increase the anticoagulant activities of Ximelagatran.Investigational
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Ximelagatran.Approved
CangrelorCangrelor may increase the anticoagulant activities of Ximelagatran.Approved
CapecitabineThe metabolism of Ximelagatran can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Ximelagatran can be increased when combined with Carbamazepine.Approved, Investigational
Carbaspirin calciumCarbaspirin calcium may increase the anticoagulant activities of Ximelagatran.Experimental
CarprofenCarprofen may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the anticoagulant activities of Ximelagatran.Experimental
CelecoxibCelecoxib may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
CeritinibThe serum concentration of Ximelagatran can be increased when it is combined with Ceritinib.Approved
CertoparinXimelagatran may increase the anticoagulant activities of Certoparin.Approved
ChloroquineChloroquine may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ximelagatran.Withdrawn
CholecalciferolThe metabolism of Ximelagatran can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
Choline magnesium trisalicylateCholine magnesium trisalicylate may increase the anticoagulant activities of Ximelagatran.Approved
CilostazolCilostazol may increase the anticoagulant activities of Ximelagatran.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Citric AcidCitric Acid may increase the anticoagulant activities of Ximelagatran.Nutraceutical, Vet Approved
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Ximelagatran.Approved
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Ximelagatran.Approved, Vet Approved
ClonixinClonixin may increase the anticoagulant activities of Ximelagatran.Approved
ClopidogrelClopidogrel may increase the anticoagulant activities of Ximelagatran.Approved, Nutraceutical
CloricromenCloricromen may increase the anticoagulant activities of Ximelagatran.Experimental
ClorindioneClorindione may increase the anticoagulant activities of Ximelagatran.Experimental
ClotrimazoleThe metabolism of Ximelagatran can be decreased when combined with Clotrimazole.Approved, Vet Approved
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Collagenase clostridium histolyticum.Approved, Investigational
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Ximelagatran.Approved
CrisaboroleThe metabolism of Ximelagatran can be decreased when combined with Crisaborole.Approved
CurcuminCurcumin may increase the anticoagulant activities of Ximelagatran.Investigational
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Ximelagatran.Approved
CyclophosphamideThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Ximelagatran.Approved, Investigational, Vet Approved
D-LimoneneD-Limonene may increase the anticoagulant activities of Ximelagatran.Investigational
DabrafenibThe serum concentration of Ximelagatran can be decreased when it is combined with Dabrafenib.Approved
DaidzeinDaidzein may decrease the anticoagulant activities of Ximelagatran.Experimental
DalteparinXimelagatran may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidXimelagatran may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanXimelagatran may increase the anticoagulant activities of Darexaban.Investigational
DasatinibDasatinib may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
DeferasiroxThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Deferasirox.Approved, Investigational
DefibrotideDefibrotide may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Ximelagatran.Approved
DemegestoneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Demegestone.Experimental
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Deoxycholic Acid.Approved
dersalazinedersalazine may increase the anticoagulant activities of Ximelagatran.Investigational
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Ximelagatran.Approved
DesirudinXimelagatran may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Ximelagatran.Investigational
DesogestrelThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Desogestrel.Approved
DextranXimelagatran may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Ximelagatran may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Ximelagatran may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Ximelagatran may increase the anticoagulant activities of Dextran 75.Approved
DibenzepinThe serum concentration of Dibenzepin can be increased when it is combined with Ximelagatran.Experimental
DiclofenacDiclofenac may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
DicoumarolDicoumarol may increase the anticoagulant activities of Ximelagatran.Approved
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Ximelagatran.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ximelagatran.Approved
DifenpiramideDifenpiramide may increase the anticoagulant activities of Ximelagatran.Experimental
DiflunisalDiflunisal may increase the anticoagulant activities of Ximelagatran.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Ximelagatran.Approved
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Ximelagatran.Approved
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Ximelagatran.Approved
DiphenadioneDiphenadione may increase the anticoagulant activities of Ximelagatran.Experimental
DipyridamoleDipyridamole may increase the anticoagulant activities of Ximelagatran.Approved
DitazoleDitazole may increase the anticoagulant activities of Ximelagatran.Approved, Withdrawn
DosulepinThe metabolism of Ximelagatran can be decreased when combined with Dosulepin.Approved
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Ximelagatran.Approved
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
DroxicamDroxicam may increase the anticoagulant activities of Ximelagatran.Approved
DuvelisibDuvelisib may increase the anticoagulant activities of Ximelagatran.Investigational
DydrogesteroneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Dydrogesterone.Approved, Withdrawn
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with Ximelagatran.Approved
E-6201E-6201 may increase the anticoagulant activities of Ximelagatran.Investigational
Edetic AcidEdetic Acid may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
EdoxabanEdoxaban may increase the anticoagulant activities of Ximelagatran.Approved
EfavirenzThe metabolism of Ximelagatran can be decreased when combined with Efavirenz.Approved, Investigational
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Ximelagatran.Approved, Investigational
EnoxaparinEnoxaparin may increase the anticoagulant activities of Ximelagatran.Approved
EpimestrolEpimestrol may decrease the anticoagulant activities of Ximelagatran.Experimental
EpinastineEpinastine may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
EpirizoleEpirizole may increase the anticoagulant activities of Ximelagatran.Approved
EplivanserinEplivanserin may increase the anticoagulant activities of Ximelagatran.Investigational
eplivanserineeplivanserine may increase the anticoagulant activities of Ximelagatran.Investigational
EpoprostenolEpoprostenol may increase the anticoagulant activities of Ximelagatran.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
EquolEquol may decrease the anticoagulant activities of Ximelagatran.Investigational
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Ximelagatran.Approved
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Ximelagatran.Approved
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Ximelagatran.Approved
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Ximelagatran.Investigational
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Ximelagatran.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Estramustine can be decreased when it is combined with Ximelagatran.Approved
EstriolEstriol may decrease the anticoagulant activities of Ximelagatran.Approved, Vet Approved
Estrogens, esterifiedThe serum concentration of Estrogens, esterified can be decreased when it is combined with Ximelagatran.Approved
EstroneEstrone may decrease the anticoagulant activities of Ximelagatran.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Ximelagatran.Approved
EtanerceptEtanercept may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
EthenzamideEthenzamide may increase the anticoagulant activities of Ximelagatran.Experimental
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Ximelagatran.Approved
Ethyl biscoumacetateXimelagatran may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the anticoagulant activities of Ximelagatran.Approved
EtonogestrelThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Etonogestrel.Approved, Investigational
EtoricoxibEtoricoxib may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Ximelagatran.Approved
Evening primrose oilEvening primrose oil may increase the anticoagulant activities of Ximelagatran.Approved
exisulindexisulind may increase the anticoagulant activities of Ximelagatran.Investigational
FelbinacFelbinac may increase the anticoagulant activities of Ximelagatran.Experimental
FenbufenFenbufen may increase the anticoagulant activities of Ximelagatran.Approved
FenoprofenFenoprofen may increase the anticoagulant activities of Ximelagatran.Approved
FentiazacFentiazac may increase the anticoagulant activities of Ximelagatran.Experimental
FeprazoneFeprazone may increase the anticoagulant activities of Ximelagatran.Experimental
Ferulic acidFerulic acid may increase the anticoagulant activities of Ximelagatran.Experimental
FibrinolysinFibrinolysin may increase the anticoagulant activities of Ximelagatran.Investigational
FloctafenineFloctafenine may increase the anticoagulant activities of Ximelagatran.Approved, Withdrawn
FloxuridineThe metabolism of Ximelagatran can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Ximelagatran can be decreased when combined with Fluconazole.Approved
FluindioneXimelagatran may increase the anticoagulant activities of Fluindione.Investigational
FlunixinFlunixin may increase the anticoagulant activities of Ximelagatran.Vet Approved
FlunoxaprofenFlunoxaprofen may increase the anticoagulant activities of Ximelagatran.Experimental
FluorouracilThe metabolism of Ximelagatran can be decreased when combined with Fluorouracil.Approved
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
FluvastatinThe metabolism of Ximelagatran can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Ximelagatran can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxXimelagatran may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumFondaparinux sodium may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
FosphenytoinThe metabolism of Ximelagatran can be increased when combined with Fosphenytoin.Approved
GabexateXimelagatran may increase the anticoagulant activities of Gabexate.Investigational
GarlicThe serum concentration of Ximelagatran can be decreased when it is combined with Garlic.Approved
GemfibrozilThe metabolism of Ximelagatran can be decreased when combined with Gemfibrozil.Approved
GenisteinGenistein may decrease the anticoagulant activities of Ximelagatran.Investigational
GestodeneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Gestodene.Approved
GestonoroneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Gestonorone.Experimental
GestrinoneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Gestrinone.Approved
GuacetisalGuacetisal may increase the anticoagulant activities of Ximelagatran.Experimental
HeminHemin may increase the anticoagulant activities of Ximelagatran.Approved
Hemoglobin crosfumarilHemoglobin crosfumaril may increase the anticoagulant activities of Ximelagatran.Experimental
HeparinHeparin may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
HexestrolThe serum concentration of Hexestrol can be decreased when it is combined with Ximelagatran.Withdrawn
HigenamineHigenamine may increase the anticoagulant activities of Ximelagatran.Investigational
Hydroxyprogesterone caproateThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
HydroxytyrosolHydroxytyrosol may increase the anticoagulant activities of Ximelagatran.Investigational
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ximelagatran.Approved
IbudilastIbudilast may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
IbuprofenIbuprofen may increase the anticoagulant activities of Ximelagatran.Approved
IbuproxamIbuproxam may increase the anticoagulant activities of Ximelagatran.Withdrawn
IcatibantIcatibant may increase the anticoagulant activities of Ximelagatran.Approved
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Ximelagatran.Approved, Nutraceutical
IdraparinuxXimelagatran may increase the anticoagulant activities of Idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Ximelagatran.Approved, Withdrawn
IfetrobanIfetroban may increase the anticoagulant activities of Ximelagatran.Investigational
IloprostIloprost may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
Imidazole salicylateImidazole salicylate may increase the anticoagulant activities of Ximelagatran.Experimental
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Ximelagatran.Approved
IndinavirThe metabolism of Ximelagatran can be decreased when combined with Indinavir.Approved
IndobufenIndobufen may increase the anticoagulant activities of Ximelagatran.Investigational
IndomethacinIndomethacin may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
IndoprofenIndoprofen may increase the anticoagulant activities of Ximelagatran.Withdrawn
IprindoleThe serum concentration of Iprindole can be increased when it is combined with Ximelagatran.Experimental
IrbesartanThe metabolism of Ximelagatran can be decreased when combined with Irbesartan.Approved, Investigational
IsoxicamIsoxicam may increase the anticoagulant activities of Ximelagatran.Withdrawn
KebuzoneKebuzone may increase the anticoagulant activities of Ximelagatran.Experimental
KetanserinKetanserin may increase the anticoagulant activities of Ximelagatran.Investigational
KetoconazoleThe metabolism of Ximelagatran can be decreased when combined with Ketoconazole.Approved, Investigational
KetoprofenKetoprofen may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
KetorolacKetorolac may increase the anticoagulant activities of Ximelagatran.Approved
LeflunomideThe metabolism of Ximelagatran can be decreased when combined with Leflunomide.Approved, Investigational
LepirudinLepirudin may increase the anticoagulant activities of Ximelagatran.Approved
LetaxabanXimelagatran may increase the anticoagulant activities of Letaxaban.Investigational
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Ximelagatran.Approved
LinsidomineLinsidomine may increase the anticoagulant activities of Ximelagatran.Experimental
LisofyllineLisofylline may increase the anticoagulant activities of Ximelagatran.Investigational
LobeglitazoneThe metabolism of Ximelagatran can be decreased when combined with Lobeglitazone.Approved
LofepramineThe serum concentration of Lofepramine can be increased when it is combined with Ximelagatran.Experimental
LonazolacLonazolac may increase the anticoagulant activities of Ximelagatran.Experimental
LornoxicamLornoxicam may increase the anticoagulant activities of Ximelagatran.Approved
LosartanThe metabolism of Ximelagatran can be decreased when combined with Losartan.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Ximelagatran.Approved, Investigational
LoxoprofenLoxoprofen may increase the anticoagulant activities of Ximelagatran.Approved
LumacaftorThe serum concentration of Ximelagatran can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Ximelagatran.Approved
ManidipineThe metabolism of Ximelagatran can be decreased when combined with Manidipine.Approved
MasoprocolMasoprocol may increase the anticoagulant activities of Ximelagatran.Approved
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
MedrogestoneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Medrogestone.Approved
Medroxyprogesterone acetateThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Medroxyprogesterone acetate.Approved, Investigational
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Ximelagatran.Approved
MelagatranXimelagatran may increase the anticoagulant activities of Melagatran.Experimental
MeloxicamMeloxicam may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
MesalazineMesalazine may increase the anticoagulant activities of Ximelagatran.Approved
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Ximelagatran.Approved
MetamizoleMetamizole may increase the anticoagulant activities of Ximelagatran.Withdrawn
MethallenestrilThe serum concentration of Methallenestril can be decreased when it is combined with Ximelagatran.Experimental
MethylergometrineThe serum concentration of Methylergometrine can be increased when it is combined with Ximelagatran.Approved
MethylestrenoloneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Methylestrenolone.Experimental
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Ximelagatran.Approved, Illicit
MidostaurinThe metabolism of Ximelagatran can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Ximelagatran can be increased when it is combined with Mifepristone.Approved, Investigational
MilrinoneMilrinone may increase the anticoagulant activities of Ximelagatran.Approved
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Ximelagatran.Approved
MizoribineMizoribine may increase the anticoagulant activities of Ximelagatran.Investigational
MofebutazoneMofebutazone may increase the anticoagulant activities of Ximelagatran.Experimental
MoxestrolMoxestrol may decrease the anticoagulant activities of Ximelagatran.Experimental
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Ximelagatran.Approved
NabumetoneNabumetone may increase the anticoagulant activities of Ximelagatran.Approved
NadroparinXimelagatran may increase the anticoagulant activities of Nadroparin.Approved
NafamostatNafamostat may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
NaftifineNaftifine may increase the anticoagulant activities of Ximelagatran.Approved
NaftopidilNaftopidil may increase the anticoagulant activities of Ximelagatran.Investigational
NaproxenNaproxen may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Ximelagatran.Approved, Withdrawn
NepafenacNepafenac may increase the anticoagulant activities of Ximelagatran.Approved
NicardipineThe metabolism of Ximelagatran can be decreased when combined with Nicardipine.Approved
NifenazoneNifenazone may increase the anticoagulant activities of Ximelagatran.Experimental
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Ximelagatran.Approved
NimesulideNimesulide may increase the anticoagulant activities of Ximelagatran.Approved, Withdrawn
NintedanibThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Nintedanib.Approved
NitroaspirinNitroaspirin may increase the anticoagulant activities of Ximelagatran.Investigational
NomegestrolThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Nomegestrol.Approved
NorethisteroneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Norethisterone.Approved
NorgestrienoneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Norgestrienone.Experimental
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Ximelagatran.Approved
ObinutuzumabThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Obinutuzumab.Approved
OlopatadineOlopatadine may increase the anticoagulant activities of Ximelagatran.Approved
OlsalazineOlsalazine may increase the anticoagulant activities of Ximelagatran.Approved
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Omacetaxine mepesuccinate.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Ximelagatran.Approved, Nutraceutical
OmeprazoleThe metabolism of Ximelagatran can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OpipramolThe serum concentration of Opipramol can be increased when it is combined with Ximelagatran.Investigational
OrgoteinOrgotein may increase the anticoagulant activities of Ximelagatran.Vet Approved
OtamixabanXimelagatran may increase the anticoagulant activities of Otamixaban.Investigational
OxaprozinOxaprozin may increase the anticoagulant activities of Ximelagatran.Approved
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Ximelagatran.Withdrawn
OzagrelOzagrel may increase the anticoagulant activities of Ximelagatran.Investigational
ParecoxibParecoxib may increase the anticoagulant activities of Ximelagatran.Approved
ParnaparinParnaparin may increase the anticoagulant activities of Ximelagatran.Approved
ParthenolideParthenolide may increase the anticoagulant activities of Ximelagatran.Investigational
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Ximelagatran.Approved
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
PethidineThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Pethidine.Approved
PhenindionePhenindione may increase the anticoagulant activities of Ximelagatran.Approved
PhenobarbitalThe metabolism of Ximelagatran can be increased when combined with Phenobarbital.Approved
PhenprocoumonPhenprocoumon may increase the anticoagulant activities of Ximelagatran.Approved
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
PhenytoinThe metabolism of Ximelagatran can be increased when combined with Phenytoin.Approved, Vet Approved
PicotamidePicotamide may increase the anticoagulant activities of Ximelagatran.Experimental
PimecrolimusPimecrolimus may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
PimozideThe serum concentration of Pimozide can be increased when it is combined with Ximelagatran.Approved
PirfenidonePirfenidone may increase the anticoagulant activities of Ximelagatran.Investigational
PiroxicamPiroxicam may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
PirprofenPirprofen may increase the anticoagulant activities of Ximelagatran.Experimental
Polyestradiol phosphatePolyestradiol phosphate may decrease the anticoagulant activities of Ximelagatran.Approved
PranoprofenPranoprofen may increase the anticoagulant activities of Ximelagatran.Experimental
PrasugrelPrasugrel may increase the anticoagulant activities of Ximelagatran.Approved
PrimidoneThe metabolism of Ximelagatran can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Progesterone.Approved, Vet Approved
ProglumetacinProglumetacin may increase the anticoagulant activities of Ximelagatran.Experimental
PromegestoneThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Promegestone.Experimental
PromestrienePromestriene may decrease the anticoagulant activities of Ximelagatran.Investigational
PropacetamolPropacetamol may increase the anticoagulant activities of Ximelagatran.Approved
PropyphenazonePropyphenazone may increase the anticoagulant activities of Ximelagatran.Experimental
ProquazoneProquazone may increase the anticoagulant activities of Ximelagatran.Experimental
Protein CXimelagatran may increase the anticoagulant activities of Protein C.Approved
Protein S humanXimelagatran may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeXimelagatran may increase the anticoagulant activities of Protocatechualdehyde.Approved
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Ximelagatran.Approved
PTC299PTC299 may increase the anticoagulant activities of Ximelagatran.Investigational
PyrimethamineThe metabolism of Ximelagatran can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinestrolQuinestrol may decrease the anticoagulant activities of Ximelagatran.Approved
QuinineThe metabolism of Ximelagatran can be decreased when combined with Quinine.Approved
RamatrobanRamatroban may increase the anticoagulant activities of Ximelagatran.Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Ximelagatran.Experimental, Investigational
ReteplaseReteplase may increase the anticoagulant activities of Ximelagatran.Approved
ReviparinXimelagatran may increase the anticoagulant activities of Reviparin.Approved
RidogrelRidogrel may increase the anticoagulant activities of Ximelagatran.Approved
RifampicinThe metabolism of Ximelagatran can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Ximelagatran can be increased when combined with Rifapentine.Approved
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Ximelagatran.Approved
RivaroxabanXimelagatran may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the anticoagulant activities of Ximelagatran.Investigational, Withdrawn
RosiglitazoneRosiglitazone may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Ximelagatran.Approved
SalicylamideSalicylamide may increase the anticoagulant activities of Ximelagatran.Approved
Salicylic acidSalicylic acid may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
SalsalateSalsalate may increase the anticoagulant activities of Ximelagatran.Approved
SarpogrelateSarpogrelate may increase the anticoagulant activities of Ximelagatran.Investigational
SaruplaseSaruplase may increase the anticoagulant activities of Ximelagatran.Experimental
SecobarbitalThe metabolism of Ximelagatran can be increased when combined with Secobarbital.Approved, Vet Approved
SecoisolariciresinolSecoisolariciresinol may decrease the anticoagulant activities of Ximelagatran.Investigational
SelexipagSelexipag may increase the anticoagulant activities of Ximelagatran.Approved
SemapimodSemapimod may increase the anticoagulant activities of Ximelagatran.Investigational
SeratrodastSeratrodast may increase the anticoagulant activities of Ximelagatran.Approved
SerrapeptaseSerrapeptase may increase the anticoagulant activities of Ximelagatran.Investigational
SevofluraneSevoflurane may increase the anticoagulant activities of Ximelagatran.Approved, Vet Approved
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Ximelagatran.Approved, Investigational
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Ximelagatran.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Ximelagatran.Approved
SorafenibThe metabolism of Ximelagatran can be decreased when combined with Sorafenib.Approved, Investigational
SRT501SRT501 may increase the anticoagulant activities of Ximelagatran.Investigational
St. John's WortThe metabolism of Ximelagatran can be increased when combined with St. John's Wort.Nutraceutical
StreptokinaseStreptokinase may increase the anticoagulant activities of Ximelagatran.Approved
SugammadexSugammadex may increase the anticoagulant activities of Ximelagatran.Approved
SulfadiazineThe metabolism of Ximelagatran can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Ximelagatran can be decreased when combined with Sulfamethoxazole.Approved
SulfasalazineSulfasalazine may increase the anticoagulant activities of Ximelagatran.Approved
SulfisoxazoleThe metabolism of Ximelagatran can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulindacSulindac may increase the anticoagulant activities of Ximelagatran.Approved
SulodexideXimelagatran may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SuprofenSuprofen may increase the anticoagulant activities of Ximelagatran.Approved, Withdrawn
SuxibuzoneSuxibuzone may increase the anticoagulant activities of Ximelagatran.Experimental
Synthetic Conjugated Estrogens, AThe serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Ximelagatran.Approved
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Ximelagatran.Approved
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Ximelagatran.Approved, Investigational
TarenflurbilTarenflurbil may increase the anticoagulant activities of Ximelagatran.Investigational
TemsirolimusThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Temsirolimus.Approved
TenecteplaseTenecteplase may increase the anticoagulant activities of Ximelagatran.Approved
TenidapTenidap may increase the anticoagulant activities of Ximelagatran.Experimental
TenoxicamTenoxicam may increase the anticoagulant activities of Ximelagatran.Approved
TepoxalinTepoxalin may increase the anticoagulant activities of Ximelagatran.Vet Approved
TeriflunomideTeriflunomide may increase the anticoagulant activities of Ximelagatran.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Ximelagatran.Investigational
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Ximelagatran.Approved
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Ximelagatran.Approved
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Ximelagatran.Approved
TiboloneTibolone may increase the anticoagulant activities of Ximelagatran.Approved
TicagrelorThe metabolism of Ximelagatran can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Ximelagatran can be decreased when combined with Ticlopidine.Approved
TinoridineTinoridine may increase the anticoagulant activities of Ximelagatran.Investigational
TinzaparinTinzaparin may increase the anticoagulant activities of Ximelagatran.Approved
TioclomarolTioclomarol may increase the anticoagulant activities of Ximelagatran.Experimental
TipranavirTipranavir may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Ximelagatran.Approved
TolbutamideThe metabolism of Ximelagatran can be decreased when combined with Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Ximelagatran.Approved
TolmetinTolmetin may increase the anticoagulant activities of Ximelagatran.Approved
TopiroxostatThe metabolism of Ximelagatran can be decreased when combined with Topiroxostat.Approved
TositumomabThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Tositumomab.Approved
TranilastTranilast may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
TrapidilTrapidil may increase the anticoagulant activities of Ximelagatran.Approved
TreprostinilTreprostinil may increase the anticoagulant activities of Ximelagatran.Approved, Investigational
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Ximelagatran.Approved
TribenosideTribenoside may increase the anticoagulant activities of Ximelagatran.Experimental
TriflusalTriflusal may increase the anticoagulant activities of Ximelagatran.Approved
TrimethoprimThe metabolism of Ximelagatran can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Ximelagatran.Approved
TriptolideTriptolide may increase the anticoagulant activities of Ximelagatran.Investigational
TroxerutinXimelagatran may increase the anticoagulant activities of Troxerutin.Investigational
UrokinaseUrokinase may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
ValdecoxibValdecoxib may increase the anticoagulant activities of Ximelagatran.Investigational, Withdrawn
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Ximelagatran.Approved, Investigational
ValsartanThe metabolism of Ximelagatran can be decreased when combined with Valsartan.Approved, Investigational
VerapamilThe metabolism of Verapamil can be decreased when combined with Ximelagatran.Approved
Vitamin EVitamin E may increase the anticoagulant activities of Ximelagatran.Approved, Nutraceutical, Vet Approved
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ximelagatran.Approved
VoriconazoleThe metabolism of Ximelagatran can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinWarfarin may increase the anticoagulant activities of Ximelagatran.Approved
ZafirlukastThe metabolism of Ximelagatran can be decreased when combined with Zafirlukast.Approved, Investigational
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Ximelagatran.Approved
ZeranolZeranol may decrease the anticoagulant activities of Ximelagatran.Vet Approved
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Ximelagatran.Approved
ZileutonZileuton may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
ZomepiracZomepirac may increase the anticoagulant activities of Ximelagatran.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference
Not 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
Human Metabolome Database
HMDB15603
PubChem Compound
9574101
PubChem Substance
46509040
ChemSpider
7848559
ChEBI
65172
ChEMBL
CHEMBL522038
Therapeutic Targets Database
DAP001218
PharmGKB
PA161748474
Wikipedia
Ximelagatran
ATC Codes
B01AE05 — Ximelagatran
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedPreventionStroke Prevention in Patients With Atrial Fibrillation1
3TerminatedPreventionThromboembolism1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Alpha amino acid esters / Alpha amino acid amides / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Amidoximes / Secondary carboxylic acid amides / Carboxylic acid esters / Azetidines / Monocarboxylic acids and derivatives / Dialkylamines
show 5 more
Substituents
Alpha-dipeptide / Alpha-amino acid ester / Alpha-amino acid amide / Alpha-amino acid or derivatives / Monocyclic benzene moiety / Benzenoid / Amidoxime / Tertiary carboxylic acid amide / Amino acid or derivatives / Azetidine
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
ethyl ester, secondary amino compound, carboxamide, azetidines, amidoxime (CHEBI:65172)

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 homeostas...
Gene Name
F2
Uniprot ID
P00734
Uniprot Name
Prothrombin
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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]

Drug created on October 21, 2007 16:23 / Updated on October 02, 2017 05:39