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Identification
NameDicoumarol
Accession NumberDB00266  (APRD00761)
TypeSmall Molecule
GroupsApproved
DescriptionAn oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem]
Structure
Thumb
Synonyms
3,3'-Methylen-bis(4-hydroxy-cumarin)
3,3'-Methylene-bis(4-hydroxycoumarine)
3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)
3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)
3,3'-Methylenebis(4-hydroxycoumarin)
bis-3,3'-(4-hydroxycoumarinyl)methane
bis-hydroxycoumarin
Bis(4-hydroxycoumarin-3-yl)methane
di-(4-hydroxy-3-coumarinyl)methane
Dicoumarol
Dicoumarolum
Dicumarol
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 BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII7QID3E7BG7
CAS number66-76-2
WeightAverage: 336.295
Monoisotopic: 336.063388116
Chemical FormulaC19H12O6
InChI KeyDOBMPNYZJYQDGZ-UHFFFAOYSA-N
InChI
InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
IUPAC Name
4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
SMILES
OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2
Pharmacology
IndicationFor decreasing blood clotting. Often used along with heparin for treatment of deep vein thrombosis.
Structured Indications Not Available
PharmacodynamicsDicumarol is an coumarin-like compound found in sweet clover. It is used as an oral anticoagulant and acts by inhibiting the hepatic synthesis of vitamin K-dependent coagulation factors (prothrombin and factors VII, IX, and X). It is also used in biochemical experiments as an inhibitor of reductases.
Mechanism of actionDicumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
TargetKindPharmacological actionActionsOrganismUniProt ID
Vitamin K epoxide reductase complex subunit 1Proteinyes
inhibitor
HumanQ9BQB6 details
NAD(P)H dehydrogenase [quinone] 1Proteinunknown
inhibitor
HumanP15559 details
Quinone oxidoreductaseProteinunknown
inhibitor
HumanQ08257 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=233 mg/kg (orally in mice); LD50=250 mg/kg (orally in rats)
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Dicumarol Action PathwayDrug actionSMP00270
Dicoumarol Action PathwayDrug actionSMP00656
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbciximabAbciximab may increase the anticoagulant activities of Dicoumarol.Approved
AbirateroneThe metabolism of Dicoumarol can be decreased when combined with Abiraterone.Approved
AceclofenacAceclofenac may increase the anticoagulant activities of Dicoumarol.Approved
AcenocoumarolDicoumarol may increase the anticoagulant activities of Acenocoumarol.Approved
AcetaminophenAcetaminophen may increase the anticoagulant activities of Dicoumarol.Approved
AcetohexamideAcetohexamide may increase the anticoagulant activities of Dicoumarol.Withdrawn
AcetovanilloneAcetovanillone may increase the anticoagulant activities of Dicoumarol.Investigational
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
AdapaleneAdapalene may increase the anticoagulant activities of Dicoumarol.Approved
AllopurinolAllopurinol may increase the anticoagulant activities of Dicoumarol.Approved
AllylestrenolThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Allylestrenol.Approved
AlprostadilAlprostadil may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
AlteplaseAlteplase may increase the anticoagulant activities of Dicoumarol.Approved
AltrenogestThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Altrenogest.Vet Approved
ALX-0081ALX-0081 may increase the anticoagulant activities of Dicoumarol.Investigational
AmdinocillinAmdinocillin may increase the anticoagulant activities of Dicoumarol.Withdrawn
AmineptineAmineptine may increase the anticoagulant activities of Dicoumarol.Illicit, Withdrawn
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Dicoumarol.Approved
AmiodaroneAmiodarone may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
AmitriptylineAmitriptyline may increase the anticoagulant activities of Dicoumarol.Approved
AmobarbitalThe metabolism of Dicoumarol can be increased when combined with Amobarbital.Approved, Illicit
AmoxicillinAmoxicillin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
AmpicillinAmpicillin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
AnagrelideAnagrelide may increase the anticoagulant activities of Dicoumarol.Approved
AncrodDicoumarol may increase the anticoagulant activities of Ancrod.Investigational
AnisodamineAnisodamine may increase the anticoagulant activities of Dicoumarol.Investigational
AnistreplaseAnistreplase may increase the anticoagulant activities of Dicoumarol.Approved
AntipyrineAntipyrine may increase the anticoagulant activities of Dicoumarol.Approved
Antithrombin III humanDicoumarol may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanApixaban may increase the anticoagulant activities of Dicoumarol.Approved
ApremilastApremilast may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
AprepitantThe metabolism of Dicoumarol can be increased when combined with Aprepitant.Approved, Investigational
AprotininThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Aprotinin.Approved, Withdrawn
ArdeparinDicoumarol may increase the anticoagulant activities of Ardeparin.Approved, Withdrawn
ArgatrobanDicoumarol may increase the anticoagulant activities of Argatroban.Approved, Investigational
AstaxanthinAstaxanthin may increase the anticoagulant activities of Dicoumarol.Investigational
AtorvastatinAtorvastatin may increase the anticoagulant activities of Dicoumarol.Approved
AzapropazoneAzapropazone may increase the anticoagulant activities of Dicoumarol.Withdrawn
AzathioprineAzathioprine may decrease the anticoagulant activities of Dicoumarol.Approved
AzelastineAzelastine may increase the anticoagulant activities of Dicoumarol.Approved
AzidocillinAzidocillin may increase the anticoagulant activities of Dicoumarol.Approved
AzithromycinThe serum concentration of Dicoumarol can be increased when it is combined with Azithromycin.Approved
AzlocillinAzlocillin may increase the anticoagulant activities of Dicoumarol.Approved
BacampicillinBacampicillin may increase the anticoagulant activities of Dicoumarol.Approved
BalsalazideBalsalazide may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
BarbexacloneThe metabolism of Dicoumarol can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Dicoumarol can be increased when combined with Barbital.Illicit
BatroxobinBatroxobin may increase the anticoagulant activities of Dicoumarol.Experimental
BazedoxifeneBazedoxifene may decrease the anticoagulant activities of Dicoumarol.Approved, Investigational
BecaplerminBecaplermin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
BemiparinBemiparin may increase the anticoagulant activities of Dicoumarol.Approved
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Dicoumarol.Withdrawn
Benzathine benzylpenicillinBenzathine benzylpenicillin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
BenzylpenicillinBenzylpenicillin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
Benzylpenicillin PotassiumBenzylpenicillin Potassium may increase the anticoagulant activities of Dicoumarol.Approved
Benzylpenicilloyl PolylysineBenzylpenicilloyl Polylysine may increase the anticoagulant activities of Dicoumarol.Approved
BeraprostBeraprost may increase the anticoagulant activities of Dicoumarol.Investigational
Betulinic AcidBetulinic Acid may increase the anticoagulant activities of Dicoumarol.Investigational
BezafibrateBezafibrate may increase the anticoagulant activities of Dicoumarol.Approved
BicalutamideThe serum concentration of Dicoumarol can be increased when it is combined with Bicalutamide.Approved
BivalirudinBivalirudin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
BosentanThe metabolism of Dicoumarol can be increased when combined with Bosentan.Approved, Investigational
BromfenacBromfenac may increase the anticoagulant activities of Dicoumarol.Approved
BucillamineBucillamine may increase the anticoagulant activities of Dicoumarol.Investigational
ButylphthalideButylphthalide may increase the anticoagulant activities of Dicoumarol.Investigational
CangrelorCangrelor may increase the anticoagulant activities of Dicoumarol.Approved
CapecitabineThe serum concentration of Dicoumarol can be increased when it is combined with Capecitabine.Approved, Investigational
CarbamazepineThe serum concentration of Dicoumarol can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarbenicillinCarbenicillin may increase the anticoagulant activities of Dicoumarol.Approved
CarbimazoleCarbimazole may decrease the anticoagulant activities of Dicoumarol.Approved
CarbomycinThe serum concentration of Dicoumarol can be increased when it is combined with Carbomycin.Vet Approved
CarindacillinCarindacillin may increase the anticoagulant activities of Dicoumarol.Approved
CarprofenCarprofen may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the anticoagulant activities of Dicoumarol.Experimental
CefacetrileCefacetrile may increase the anticoagulant activities of Dicoumarol.Approved
CefaclorCefaclor may increase the anticoagulant activities of Dicoumarol.Approved
CefadroxilCefadroxil may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved, Withdrawn
CefalotinCefalotin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
CefamandoleCefamandole may increase the anticoagulant activities of Dicoumarol.Approved
CefapirinCefapirin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
CefazolinCefazolin may increase the anticoagulant activities of Dicoumarol.Approved
CefiximeCefixime may increase the anticoagulant activities of Dicoumarol.Approved
CefmenoximeCefmenoxime may increase the anticoagulant activities of Dicoumarol.Approved
CefmetazoleCefmetazole may increase the anticoagulant activities of Dicoumarol.Approved
CefminoxCefminox may increase the anticoagulant activities of Dicoumarol.Approved
CefonicidCefonicid may increase the anticoagulant activities of Dicoumarol.Approved
CefoperazoneCefoperazone may increase the anticoagulant activities of Dicoumarol.Approved
CeforanideCeforanide may increase the anticoagulant activities of Dicoumarol.Approved
CefotaximeCefotaxime may increase the anticoagulant activities of Dicoumarol.Approved
CefotetanCefotetan may increase the anticoagulant activities of Dicoumarol.Approved
CefotiamCefotiam may increase the anticoagulant activities of Dicoumarol.Approved
CefoxitinCefoxitin may increase the anticoagulant activities of Dicoumarol.Approved
CefpodoximeCefpodoxime may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
CefradineCefradine may increase the anticoagulant activities of Dicoumarol.Approved
CefroxadineCefroxadine may increase the anticoagulant activities of Dicoumarol.Approved
CeftazidimeCeftazidime may increase the anticoagulant activities of Dicoumarol.Approved
CeftizoximeCeftizoxime may increase the anticoagulant activities of Dicoumarol.Approved
CeftriaxoneCeftriaxone may increase the anticoagulant activities of Dicoumarol.Approved
CefuroximeCefuroxime may increase the anticoagulant activities of Dicoumarol.Approved
CelecoxibCelecoxib may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
CephalexinCephalexin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
CephaloglycinCephaloglycin may increase the anticoagulant activities of Dicoumarol.Approved
CephaloridineCephaloridine may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
CeritinibThe serum concentration of Dicoumarol can be increased when it is combined with Ceritinib.Approved
CerivastatinCerivastatin may increase the anticoagulant activities of Dicoumarol.Withdrawn
CertoparinDicoumarol may increase the anticoagulant activities of Certoparin.Approved
Chloral hydrateThe serum concentration of Dicoumarol can be increased when it is combined with Chloral hydrate.Approved, Illicit, Vet Approved
ChloramphenicolChloramphenicol may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
ChloroquineChloroquine may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Dicoumarol.Withdrawn
ChlorpropamideChlorpropamide may increase the anticoagulant activities of Dicoumarol.Approved
ChlortetracyclineChlortetracycline may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
CholecalciferolThe metabolism of Dicoumarol can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholestyramineCholestyramine can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CilostazolCilostazol may increase the anticoagulant activities of Dicoumarol.Approved
CimetidineCimetidine may increase the anticoagulant activities of Dicoumarol.Approved
CinoxacinCinoxacin may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
CiprofibrateCiprofibrate may increase the anticoagulant activities of Dicoumarol.Approved
CiprofloxacinCiprofloxacin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
CitalopramCitalopram may increase the anticoagulant activities of Dicoumarol.Approved
Citric AcidDicoumarol may increase the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClarithromycinThe serum concentration of Dicoumarol can be increased when it is combined with Clarithromycin.Approved
ClofibrateClofibrate may increase the anticoagulant activities of Dicoumarol.Approved
ClomipramineClomipramine may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
ClonixinClonixin may increase the anticoagulant activities of Dicoumarol.Approved
ClopidogrelClopidogrel may increase the anticoagulant activities of Dicoumarol.Approved, Nutraceutical
ClotrimazoleThe metabolism of Dicoumarol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CloxacillinCloxacillin may decrease the anticoagulant activities of Dicoumarol.Approved, Vet Approved
Coenzyme Q10Coenzyme Q10 may decrease the anticoagulant activities of Dicoumarol.Experimental
ColesevelamColesevelam can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CollagenaseThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Collagenase.Approved
Conjugated Equine EstrogensConjugated Equine Estrogens may decrease the anticoagulant activities of Dicoumarol.Approved
CranberryCranberry may increase the anticoagulant activities of Dicoumarol.Approved
CurcuminCurcumin may increase the anticoagulant activities of Dicoumarol.Investigational
CyclacillinCyclacillin may increase the anticoagulant activities of Dicoumarol.Approved
CyclobenzaprineCyclobenzaprine may increase the anticoagulant activities of Dicoumarol.Approved
CyclosporineThe metabolism of Dicoumarol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
D-LimoneneD-Limonene may increase the anticoagulant activities of Dicoumarol.Investigational
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Dicoumarol.Approved
DabrafenibThe serum concentration of Dicoumarol can be decreased when it is combined with Dabrafenib.Approved
DalteparinDicoumarol may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidDicoumarol may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DapoxetineDapoxetine may increase the anticoagulant activities of Dicoumarol.Investigational
DasatinibDasatinib may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
DeferasiroxThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Deferasirox.Approved, Investigational
DefibrotideDefibrotide may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
DelavirdineThe metabolism of Dicoumarol can be decreased when combined with Delavirdine.Approved
DemeclocyclineDemeclocycline may increase the anticoagulant activities of Dicoumarol.Approved
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Deoxycholic Acid.Approved
dersalazinedersalazine may increase the anticoagulant activities of Dicoumarol.Investigational
DesipramineDesipramine may increase the anticoagulant activities of Dicoumarol.Approved
DesirudinDicoumarol may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Dicoumarol.Investigational
DesogestrelDesogestrel may decrease the anticoagulant activities of Dicoumarol.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Dicoumarol.Approved
DexmethylphenidateThe serum concentration of Dicoumarol can be increased when it is combined with Dexmethylphenidate.Approved
DextranDicoumarol may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Dicoumarol may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Dicoumarol may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Dicoumarol may increase the anticoagulant activities of Dextran 75.Approved
DiclofenacDiclofenac may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
DicloxacillinDicloxacillin may decrease the anticoagulant activities of Dicoumarol.Approved, Vet Approved
DienestrolDienestrol may decrease the anticoagulant activities of Dicoumarol.Approved
DienogestDienogest may decrease the anticoagulant activities of Dicoumarol.Approved
DiethylstilbestrolDiethylstilbestrol may decrease the anticoagulant activities of Dicoumarol.Approved
DiflunisalDiflunisal may increase the anticoagulant activities of Dicoumarol.Approved
DihydrotestosteroneDihydrotestosterone may increase the anticoagulant activities of Dicoumarol.Illicit
DipyridamoleDipyridamole may increase the anticoagulant activities of Dicoumarol.Approved
DisulfiramThe serum concentration of Dicoumarol can be increased when it is combined with Disulfiram.Approved
DitazoleDitazole may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
DosulepinDosulepin may increase the anticoagulant activities of Dicoumarol.Approved
DoxepinDoxepin may increase the anticoagulant activities of Dicoumarol.Approved
DoxycyclineDoxycycline may increase the anticoagulant activities of Dicoumarol.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Dicoumarol can be increased when it is combined with Dronedarone.Approved
DrospirenoneDrospirenone may decrease the anticoagulant activities of Dicoumarol.Approved
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Dicoumarol.Approved, Investigational, Withdrawn
DroxicamDroxicam may increase the anticoagulant activities of Dicoumarol.Approved
DuloxetineDuloxetine may increase the anticoagulant activities of Dicoumarol.Approved
DuvelisibDuvelisib may increase the anticoagulant activities of Dicoumarol.Investigational
DydrogesteroneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Dydrogesterone.Approved, Withdrawn
E6201E6201 may increase the anticoagulant activities of Dicoumarol.Investigational
EbselenEbselen may increase the anticoagulant activities of Dicoumarol.Investigational
EconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Econazole.Approved
Edetic AcidDicoumarol may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanEdoxaban may increase the anticoagulant activities of Dicoumarol.Approved
EfavirenzThe serum concentration of Dicoumarol can be decreased when it is combined with Efavirenz.Approved, Investigational
EnoxacinEnoxacin may increase the anticoagulant activities of Dicoumarol.Approved
EnoxaparinDicoumarol may increase the anticoagulant activities of Enoxaparin.Approved
EpinastineEpinastine may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
EpirizoleEpirizole may increase the anticoagulant activities of Dicoumarol.Approved
eplivanserineeplivanserine may increase the anticoagulant activities of Dicoumarol.Investigational
EpoprostenolEpoprostenol may increase the anticoagulant activities of Dicoumarol.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
ErythromycinThe serum concentration of Dicoumarol can be increased when it is combined with Erythromycin.Approved, Vet Approved
EscitalopramEscitalopram may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
EsmirtazapineEsmirtazapine may increase the anticoagulant activities of Dicoumarol.Investigational
EsomeprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Esomeprazole.Approved, Investigational
EstradiolEstradiol may decrease the anticoagulant activities of Dicoumarol.Approved, Investigational, Vet Approved
EstramustineEstramustine may decrease the anticoagulant activities of Dicoumarol.Approved
EstriolEstriol may decrease the anticoagulant activities of Dicoumarol.Approved, Vet Approved
Estrogens, esterifiedEstrogens, esterified may decrease the anticoagulant activities of Dicoumarol.Approved
EstroneEstrone may decrease the anticoagulant activities of Dicoumarol.Approved
Estrone sulfateEstrone sulfate may decrease the anticoagulant activities of Dicoumarol.Approved
Etacrynic acidThe serum concentration of Dicoumarol can be increased when it is combined with Etacrynic acid.Approved
EtanerceptEtanercept may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
EthanolThe serum concentration of Dicoumarol can be decreased when it is combined with Ethanol.Approved
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Dicoumarol.Approved
EthotoinEthotoin may increase the anticoagulant activities of Dicoumarol.Approved
Ethyl biscoumacetateDicoumarol may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Ethynodiol diacetateEthynodiol diacetate may decrease the anticoagulant activities of Dicoumarol.Approved
EtodolacEtodolac may increase the anticoagulant activities of Dicoumarol.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the anticoagulant activities of Dicoumarol.Approved
EtofibrateEtofibrate may increase the anticoagulant activities of Dicoumarol.Approved
EtonogestrelEtonogestrel may decrease the anticoagulant activities of Dicoumarol.Approved, Investigational
EtoperidoneEtoperidone may increase the anticoagulant activities of Dicoumarol.Approved
EtoposideEtoposide may increase the anticoagulant activities of Dicoumarol.Approved
EtoricoxibEtoricoxib may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
EtravirineThe metabolism of Dicoumarol can be decreased when combined with Etravirine.Approved
Evening primrose oilEvening primrose oil may increase the anticoagulant activities of Dicoumarol.Approved
ExenatideExenatide may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
exisulindexisulind may increase the anticoagulant activities of Dicoumarol.Investigational
FenbufenFenbufen may increase the anticoagulant activities of Dicoumarol.Approved
FenofibrateFenofibrate may increase the anticoagulant activities of Dicoumarol.Approved
FenoprofenFenoprofen may increase the anticoagulant activities of Dicoumarol.Approved
FibrinolysinFibrinolysin may increase the anticoagulant activities of Dicoumarol.Approved
FleroxacinFleroxacin may increase the anticoagulant activities of Dicoumarol.Approved
FloctafenineFloctafenine may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
FloxuridineThe metabolism of Dicoumarol can be decreased when combined with Floxuridine.Approved
FlucloxacillinFlucloxacillin may decrease the anticoagulant activities of Dicoumarol.Approved
FluconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Fluconazole.Approved
FluindioneDicoumarol may increase the anticoagulant activities of Fluindione.Investigational
FlumequineFlumequine may increase the anticoagulant activities of Dicoumarol.Withdrawn
FlunixinFlunixin may increase the anticoagulant activities of Dicoumarol.Vet Approved
FluorouracilThe serum concentration of Dicoumarol can be increased when it is combined with Fluorouracil.Approved
FluorouracilThe metabolism of Dicoumarol can be decreased when combined with Fluorouracil.Approved
FluoxetineFluoxetine may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
FluoxymesteroneFluoxymesterone may increase the anticoagulant activities of Dicoumarol.Approved, Illicit
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
FluvastatinThe metabolism of Dicoumarol can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Dicoumarol can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxDicoumarol may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumDicoumarol may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FosphenytoinFosphenytoin may increase the anticoagulant activities of Dicoumarol.Approved
Fusidic AcidThe serum concentration of Dicoumarol can be increased when it is combined with Fusidic Acid.Approved
GabexateDicoumarol may increase the anticoagulant activities of Gabexate.Investigational
GarenoxacinGarenoxacin may increase the anticoagulant activities of Dicoumarol.Investigational
GatifloxacinGatifloxacin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
GefitinibGefitinib may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
GemfibrozilGemfibrozil may increase the anticoagulant activities of Dicoumarol.Approved
GemifloxacinGemifloxacin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
GenisteinGenistein may decrease the anticoagulant activities of Dicoumarol.Investigational
GestodeneGestodene may decrease the anticoagulant activities of Dicoumarol.Approved
GestrinoneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Gestrinone.Approved
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Ginkgo biloba is combined with Dicoumarol.Approved, Nutraceutical
GlibornurideGlibornuride may increase the anticoagulant activities of Dicoumarol.Withdrawn
GliclazideGliclazide may increase the anticoagulant activities of Dicoumarol.Approved
GlimepirideGlimepiride may increase the anticoagulant activities of Dicoumarol.Approved
GlipizideGlipizide may increase the anticoagulant activities of Dicoumarol.Approved
GliquidoneGliquidone may increase the anticoagulant activities of Dicoumarol.Approved
GlisoxepideGlisoxepide may increase the anticoagulant activities of Dicoumarol.Approved
Glucagon recombinantGlucagon recombinant may increase the anticoagulant activities of Dicoumarol.Approved
GlutethimideThe metabolism of Dicoumarol can be increased when combined with Glutethimide.Approved, Illicit
GlyburideGlyburide may increase the anticoagulant activities of Dicoumarol.Approved
GrepafloxacinGrepafloxacin may increase the anticoagulant activities of Dicoumarol.Withdrawn
GriseofulvinThe serum concentration of Dicoumarol can be decreased when it is combined with Griseofulvin.Approved, Vet Approved
HeminHemin may increase the anticoagulant activities of Dicoumarol.Approved
HeparinDicoumarol may increase the anticoagulant activities of Heparin.Approved, Investigational
HexestrolHexestrol may decrease the anticoagulant activities of Dicoumarol.Withdrawn
HexobarbitalThe metabolism of Dicoumarol can be increased when combined with Hexobarbital.Approved
HigenamineHigenamine may increase the anticoagulant activities of Dicoumarol.Investigational
HirulogDicoumarol may increase the anticoagulant activities of Hirulog.Experimental
HMPL-004HMPL-004 may increase the anticoagulant activities of Dicoumarol.Investigational
Hydroxyprogesterone caproateThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dicoumarol.Approved
IbudilastIbudilast may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
IbuprofenIbuprofen may increase the anticoagulant activities of Dicoumarol.Approved
IbuproxamIbuproxam may increase the anticoagulant activities of Dicoumarol.Withdrawn
IcatibantIcatibant may increase the anticoagulant activities of Dicoumarol.Approved
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Dicoumarol.Approved, Nutraceutical
idraparinuxDicoumarol may increase the anticoagulant activities of idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
IfosfamideIfosfamide may increase the anticoagulant activities of Dicoumarol.Approved
IloprostIloprost may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
ImipramineImipramine may increase the anticoagulant activities of Dicoumarol.Approved
IndalpineIndalpine may increase the anticoagulant activities of Dicoumarol.Investigational, Withdrawn
IndinavirThe metabolism of Dicoumarol can be decreased when combined with Indinavir.Approved
IndobufenIndobufen may increase the anticoagulant activities of Dicoumarol.Investigational
IndomethacinIndomethacin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
IndoprofenIndoprofen may increase the anticoagulant activities of Dicoumarol.Withdrawn
IrbesartanThe metabolism of Dicoumarol can be decreased when combined with Irbesartan.Approved, Investigational
IsoxicamIsoxicam may increase the anticoagulant activities of Dicoumarol.Withdrawn
ItraconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Itraconazole.Approved, Investigational
IvermectinIvermectin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
JosamycinThe serum concentration of Dicoumarol can be increased when it is combined with Josamycin.Approved
Kct 0809Kct 0809 may increase the anticoagulant activities of Dicoumarol.Investigational
KebuzoneKebuzone may increase the anticoagulant activities of Dicoumarol.Experimental
KetanserinKetanserin may increase the anticoagulant activities of Dicoumarol.Investigational
KetoconazoleThe metabolism of Dicoumarol can be decreased when combined with Ketoconazole.Approved, Investigational
KetoconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Ketoconazole.Approved, Investigational
KetoprofenKetoprofen may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
KetorolacKetorolac may increase the anticoagulant activities of Dicoumarol.Approved
KitasamycinThe serum concentration of Dicoumarol can be increased when it is combined with Kitasamycin.Experimental
L-CarnitineL-Carnitine may increase the anticoagulant activities of Dicoumarol.Approved
LansoprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Lansoprazole.Approved, Investigational
LeflunomideLeflunomide may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
LepirudinLepirudin may increase the anticoagulant activities of Dicoumarol.Approved
LevofloxacinLevofloxacin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Dicoumarol.Approved
LevonorgestrelLevonorgestrel may decrease the anticoagulant activities of Dicoumarol.Approved, Investigational
LevothyroxineLevothyroxine may increase the anticoagulant activities of Dicoumarol.Approved
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Dicoumarol.Approved
LiothyronineLiothyronine may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
LiotrixLiotrix may increase the anticoagulant activities of Dicoumarol.Approved
LisofyllineLisofylline may increase the anticoagulant activities of Dicoumarol.Investigational
LixisenatideLixisenatide can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
LomefloxacinLomefloxacin may increase the anticoagulant activities of Dicoumarol.Approved
LornoxicamLornoxicam may increase the anticoagulant activities of Dicoumarol.Approved
LosartanThe metabolism of Dicoumarol can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Dicoumarol can be decreased when combined with Lovastatin.Approved, Investigational
LoxoprofenLoxoprofen may increase the anticoagulant activities of Dicoumarol.Approved
LumacaftorThe serum concentration of Dicoumarol can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
LynestrenolLynestrenol may decrease the anticoagulant activities of Dicoumarol.Investigational
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Dicoumarol.Approved
MasoprocolMasoprocol may increase the anticoagulant activities of Dicoumarol.Approved
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
MedrogestoneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Medrogestone.Approved
Medroxyprogesterone acetateMedroxyprogesterone acetate may decrease the anticoagulant activities of Dicoumarol.Approved, Investigational
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Dicoumarol.Approved
Megestrol acetateThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Megestrol acetate.Approved, Vet Approved
MeloxicamMeloxicam may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
MercaptopurineMercaptopurine may decrease the anticoagulant activities of Dicoumarol.Approved
MesalazineMesalazine may increase the anticoagulant activities of Dicoumarol.Approved
MestranolMestranol may decrease the anticoagulant activities of Dicoumarol.Approved
MetamizoleMetamizole may increase the anticoagulant activities of Dicoumarol.Withdrawn
MethallenestrilMethallenestril may decrease the anticoagulant activities of Dicoumarol.Experimental
MethimazoleMethimazole may decrease the anticoagulant activities of Dicoumarol.Approved
MethohexitalThe metabolism of Dicoumarol can be increased when combined with Methohexital.Approved
MethylphenidateThe serum concentration of Dicoumarol can be increased when it is combined with Methylphenidate.Approved, Investigational
MethylphenobarbitalThe metabolism of Dicoumarol can be increased when combined with Methylphenobarbital.Approved
MethyltestosteroneMethyltestosterone may increase the anticoagulant activities of Dicoumarol.Approved
MeticillinMeticillin may increase the anticoagulant activities of Dicoumarol.Approved
MetronidazoleThe serum concentration of Dicoumarol can be increased when it is combined with Metronidazole.Approved
MevastatinMevastatin may increase the anticoagulant activities of Dicoumarol.Experimental
MezlocillinMezlocillin may increase the anticoagulant activities of Dicoumarol.Approved
MiconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MifepristoneThe serum concentration of Dicoumarol can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Dicoumarol.Approved
MilrinoneMilrinone may increase the anticoagulant activities of Dicoumarol.Approved
MinocyclineMinocycline may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
MirtazapineMirtazapine may increase the anticoagulant activities of Dicoumarol.Approved
MizoribineMizoribine may increase the anticoagulant activities of Dicoumarol.Investigational
MoxifloxacinMoxifloxacin may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Dicoumarol.Approved
NabumetoneNabumetone may increase the anticoagulant activities of Dicoumarol.Approved
NadroparinDicoumarol may increase the anticoagulant activities of Nadroparin.Approved
NafamostatNafamostat may increase the anticoagulant activities of Dicoumarol.Investigational
NafcillinNafcillin may decrease the anticoagulant activities of Dicoumarol.Approved
NaftifineNaftifine may increase the anticoagulant activities of Dicoumarol.Approved
NaftopidilNaftopidil may increase the anticoagulant activities of Dicoumarol.Investigational
Nalidixic AcidNalidixic Acid may increase the anticoagulant activities of Dicoumarol.Approved
NaproxenNaproxen may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
NCX 4016NCX 4016 may increase the anticoagulant activities of Dicoumarol.Investigational
NefazodoneNefazodone may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
NemonoxacinNemonoxacin may increase the anticoagulant activities of Dicoumarol.Investigational
NeomycinNeomycin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
NepafenacNepafenac may increase the anticoagulant activities of Dicoumarol.Approved
NicardipineThe metabolism of Dicoumarol can be decreased when combined with Nicardipine.Approved
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Dicoumarol.Approved
NimesulideNimesulide may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
NintedanibThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Nintedanib.Approved
NitroaspirinNitroaspirin may increase the anticoagulant activities of Dicoumarol.Investigational
NomegestrolThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Nomegestrol.Approved
NorelgestrominNorelgestromin may decrease the anticoagulant activities of Dicoumarol.Approved
NorethisteroneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Norethisterone.Approved
NorfloxacinNorfloxacin may increase the anticoagulant activities of Dicoumarol.Approved
NorgestimateNorgestimate may decrease the anticoagulant activities of Dicoumarol.Approved
NorgestrelNorgestrel may decrease the anticoagulant activities of Dicoumarol.Approved
NortriptylineNortriptyline may increase the anticoagulant activities of Dicoumarol.Approved
ObinutuzumabThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Obinutuzumab.Approved
OfloxacinOfloxacin may increase the anticoagulant activities of Dicoumarol.Approved
OleandomycinThe serum concentration of Dicoumarol can be increased when it is combined with Oleandomycin.Vet Approved
OlopatadineOlopatadine may increase the anticoagulant activities of Dicoumarol.Approved
OlsalazineOlsalazine may increase the anticoagulant activities of Dicoumarol.Approved
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Omacetaxine mepesuccinate.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Dicoumarol.Approved
OmeprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OpipramolOpipramol may increase the anticoagulant activities of Dicoumarol.Investigational
OrgoteinOrgotein may increase the anticoagulant activities of Dicoumarol.Vet Approved
OritavancinThe serum concentration of Dicoumarol can be increased when it is combined with Oritavancin.Approved, Investigational
OtamixabanDicoumarol may increase the anticoagulant activities of Otamixaban.Investigational
OxacillinOxacillin may increase the anticoagulant activities of Dicoumarol.Approved
OxandroloneOxandrolone may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
OxaprozinOxaprozin may increase the anticoagulant activities of Dicoumarol.Approved
OxymetholoneOxymetholone may increase the anticoagulant activities of Dicoumarol.Approved, Illicit
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Dicoumarol.Withdrawn
OxytetracyclineOxytetracycline may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
ParecoxibParecoxib may increase the anticoagulant activities of Dicoumarol.Approved
ParnaparinParnaparin may increase the anticoagulant activities of Dicoumarol.Approved
ParoxetineParoxetine may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
PazufloxacinPazufloxacin may increase the anticoagulant activities of Dicoumarol.Investigational
PefloxacinPefloxacin may increase the anticoagulant activities of Dicoumarol.Approved
PentobarbitalThe metabolism of Dicoumarol can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Dicoumarol.Approved
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
PhenindioneDicoumarol may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Dicoumarol can be increased when combined with Phenobarbital.Approved
PhenoxymethylpenicillinPhenoxymethylpenicillin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
PhenprocoumonDicoumarol may increase the anticoagulant activities of Phenprocoumon.Approved
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
PhenytoinPhenytoin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
PhylloquinonePhylloquinone may decrease the anticoagulant activities of Dicoumarol.Approved
PimecrolimusPimecrolimus may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
PiperacillinPiperacillin may increase the anticoagulant activities of Dicoumarol.Approved
PirfenidonePirfenidone may increase the anticoagulant activities of Dicoumarol.Investigational
PiroxicamPiroxicam may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
PitavastatinPitavastatin may increase the anticoagulant activities of Dicoumarol.Approved
PivampicillinPivampicillin may increase the anticoagulant activities of Dicoumarol.Approved
PivmecillinamPivmecillinam may increase the anticoagulant activities of Dicoumarol.Approved
PlasminPlasmin may increase the anticoagulant activities of Dicoumarol.Investigational
Polyestradiol phosphatePolyestradiol phosphate may decrease the anticoagulant activities of Dicoumarol.Approved
PosaconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrasugrelPrasugrel may increase the anticoagulant activities of Dicoumarol.Approved
PravastatinPravastatin may increase the anticoagulant activities of Dicoumarol.Approved
PrimidoneThe metabolism of Dicoumarol can be increased when combined with Primidone.Approved, Vet Approved
Procaine benzylpenicillinProcaine benzylpenicillin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
ProgesteroneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Progesterone.Approved, Vet Approved
PromestrienePromestriene may decrease the anticoagulant activities of Dicoumarol.Investigational
PropacetamolPropacetamol may increase the anticoagulant activities of Dicoumarol.Approved
PropafenoneThe serum concentration of Dicoumarol can be increased when it is combined with Propafenone.Approved
PropylthiouracilPropylthiouracil may decrease the anticoagulant activities of Dicoumarol.Approved
Protein CDicoumarol may increase the anticoagulant activities of Protein C.Approved
Protein S humanDicoumarol may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeDicoumarol may increase the anticoagulant activities of Protocatechualdehyde.Approved
ProtriptylineProtriptyline may increase the anticoagulant activities of Dicoumarol.Approved
PrulifloxacinPrulifloxacin may increase the anticoagulant activities of Dicoumarol.Investigational
PTC299PTC299 may increase the anticoagulant activities of Dicoumarol.Investigational
PyrimethamineThe metabolism of Dicoumarol can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinestrolQuinestrol may decrease the anticoagulant activities of Dicoumarol.Approved
QuinidineQuinidine may increase the anticoagulant activities of Dicoumarol.Approved
QuinineQuinine may increase the anticoagulant activities of Dicoumarol.Approved
RamatrobanRamatroban may increase the anticoagulant activities of Dicoumarol.Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Dicoumarol.Experimental, Investigational
ReteplaseReteplase may increase the anticoagulant activities of Dicoumarol.Approved
ReviparinDicoumarol may increase the anticoagulant activities of Reviparin.Approved
RidogrelRidogrel may increase the anticoagulant activities of Dicoumarol.Approved
RifabutinThe metabolism of Dicoumarol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Dicoumarol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Dicoumarol can be increased when combined with Rifapentine.Approved
RivaroxabanDicoumarol may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the anticoagulant activities of Dicoumarol.Investigational, Withdrawn
RosiglitazoneRosiglitazone may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
RosoxacinRosoxacin may increase the anticoagulant activities of Dicoumarol.Approved
RosuvastatinRosuvastatin may increase the anticoagulant activities of Dicoumarol.Approved
S EquolS Equol may decrease the anticoagulant activities of Dicoumarol.Investigational
SalicylamideSalicylamide may increase the anticoagulant activities of Dicoumarol.Approved
Salicylic acidSalicylic acid may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
SalsalateSalsalate may increase the anticoagulant activities of Dicoumarol.Approved
SCH-530348SCH-530348 may increase the anticoagulant activities of Dicoumarol.Investigational
SecobarbitalThe metabolism of Dicoumarol can be increased when combined with Secobarbital.Approved, Vet Approved
SecoisolariciresinolSecoisolariciresinol may decrease the anticoagulant activities of Dicoumarol.Investigational
SelexipagSelexipag may increase the anticoagulant activities of Dicoumarol.Approved
SeratrodastSeratrodast may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
SertralineSertraline may increase the anticoagulant activities of Dicoumarol.Approved
SevofluraneSevoflurane may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
SildenafilThe metabolism of Dicoumarol can be decreased when combined with Sildenafil.Approved, Investigational
SimvastatinSimvastatin may increase the anticoagulant activities of Dicoumarol.Approved
SolithromycinThe serum concentration of Dicoumarol can be increased when it is combined with Solithromycin.Investigational
SorafenibThe metabolism of Dicoumarol can be decreased when combined with Sorafenib.Approved, Investigational
SparfloxacinSparfloxacin may increase the anticoagulant activities of Dicoumarol.Approved
SRT501SRT501 may increase the anticoagulant activities of Dicoumarol.Investigational
St. John's WortThe metabolism of Dicoumarol can be increased when combined with St. John's Wort.Nutraceutical
StanozololStanozolol may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
StreptokinaseStreptokinase may increase the anticoagulant activities of Dicoumarol.Approved
SucralfateSucralfate may decrease the anticoagulant activities of Dicoumarol.Approved
SugammadexSugammadex may increase the anticoagulant activities of Dicoumarol.Approved
SulbactamSulbactam may increase the anticoagulant activities of Dicoumarol.Approved
SulfadiazineThe metabolism of Dicoumarol can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleSulfamethoxazole may increase the anticoagulant activities of Dicoumarol.Approved
SulfasalazineSulfasalazine may increase the anticoagulant activities of Dicoumarol.Approved
SulfinpyrazoneThe metabolism of Dicoumarol can be decreased when combined with Sulfinpyrazone.Approved
SulfisoxazoleThe metabolism of Dicoumarol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulindacSulindac may increase the anticoagulant activities of Dicoumarol.Approved
SulodexideDicoumarol may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SultamicillinSultamicillin may increase the anticoagulant activities of Dicoumarol.Investigational
SuprofenSuprofen may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Dicoumarol.Approved
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Dicoumarol.Approved
TamoxifenThe serum concentration of Dicoumarol can be increased when it is combined with Tamoxifen.Approved
TazobactamTazobactam may increase the anticoagulant activities of Dicoumarol.Approved
TegafurThe serum concentration of Dicoumarol can be increased when it is combined with Tegafur.Approved
TelithromycinThe serum concentration of Dicoumarol can be increased when it is combined with Telithromycin.Approved
TemafloxacinTemafloxacin may increase the anticoagulant activities of Dicoumarol.Withdrawn
TenecteplaseTenecteplase may increase the anticoagulant activities of Dicoumarol.Approved
TenoxicamTenoxicam may increase the anticoagulant activities of Dicoumarol.Approved
TepoxalinTepoxalin may increase the anticoagulant activities of Dicoumarol.Vet Approved
TeriflunomideTeriflunomide may increase the anticoagulant activities of Dicoumarol.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Dicoumarol.Investigational
TestosteroneTestosterone may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
TetracyclineTetracycline may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
ThiamylalThe metabolism of Dicoumarol can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Dicoumarol can be increased when combined with Thiopental.Approved, Vet Approved
Thyroid, porcineThyroid, porcine may increase the anticoagulant activities of Dicoumarol.Approved
TianeptineTianeptine may increase the anticoagulant activities of Dicoumarol.Approved
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Dicoumarol.Approved
TiboloneTibolone may increase the anticoagulant activities of Dicoumarol.Approved
TicagrelorThe metabolism of Dicoumarol can be decreased when combined with Ticagrelor.Approved
TicarcillinTicarcillin may increase the anticoagulant activities of Dicoumarol.Approved, Vet Approved
TiclopidineThe metabolism of Dicoumarol can be decreased when combined with Ticlopidine.Approved
TinoridineTinoridine may increase the anticoagulant activities of Dicoumarol.Investigational
TinzaparinTinzaparin may increase the anticoagulant activities of Dicoumarol.Approved
TipranavirTipranavir may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Dicoumarol.Approved
TolazamideTolazamide may increase the anticoagulant activities of Dicoumarol.Approved
TolbutamideThe metabolism of Dicoumarol can be decreased when combined with Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Dicoumarol.Approved
TolmetinTolmetin may increase the anticoagulant activities of Dicoumarol.Approved
ToremifeneToremifene may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
TositumomabThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Tositumomab.Approved
TramadolTramadol may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
TranilastTranilast may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
TrapidilTrapidil may increase the anticoagulant activities of Dicoumarol.Approved
TreprostinilTreprostinil may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
TriflusalTriflusal may increase the anticoagulant activities of Dicoumarol.Approved
TrimethoprimThe metabolism of Dicoumarol can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineTrimipramine may increase the anticoagulant activities of Dicoumarol.Approved
Trisalicylate-cholineTrisalicylate-choline may increase the anticoagulant activities of Dicoumarol.Approved
TroleandomycinThe serum concentration of Dicoumarol can be increased when it is combined with Troleandomycin.Approved
TrovafloxacinTrovafloxacin may increase the anticoagulant activities of Dicoumarol.Approved, Withdrawn
TylosinThe serum concentration of Dicoumarol can be increased when it is combined with Tylosin.Vet Approved
UrokinaseUrokinase may increase the anticoagulant activities of Dicoumarol.Approved, Investigational, Withdrawn
ValdecoxibValdecoxib may increase the anticoagulant activities of Dicoumarol.Investigational, Withdrawn
Valproic AcidThe metabolism of Dicoumarol can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Dicoumarol can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Dicoumarol.Approved
Vitamin EVitamin E may increase the anticoagulant activities of Dicoumarol.Approved, Nutraceutical, Vet Approved
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Dicoumarol.Approved
VoriconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Voriconazole.Approved, Investigational
VorinostatVorinostat may increase the anticoagulant activities of Dicoumarol.Approved, Investigational
WarfarinDicoumarol may increase the anticoagulant activities of Warfarin.Approved
XimelagatranDicoumarol may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Ym150Dicoumarol may increase the anticoagulant activities of Ym150.Investigational
ZafirlukastThe serum concentration of Dicoumarol can be increased when it is combined with Zafirlukast.Approved, Investigational
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Dicoumarol.Approved
ZeranolZeranol may decrease the anticoagulant activities of Dicoumarol.Vet Approved
ZileutonZileuton may increase the anticoagulant activities of Dicoumarol.Approved, Investigational, Withdrawn
ZimelidineZimelidine may increase the anticoagulant activities of Dicoumarol.Withdrawn
ZomepiracZomepirac may increase the anticoagulant activities of Dicoumarol.Withdrawn
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, Weydert CJ, Domann FE, Oberley LW: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism. Cancer Res. 2003 Sep 1;63(17):5513-20. [PubMed:14500388 ]
  2. Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA Jr, Fusella A, Di Tullio G, Silletta MG, Corda D, De Matteis MA, Luini A: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport. Eur J Cell Biol. 2004 Jul;83(6):263-79. [PubMed:15511084 ]
  3. Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. [PubMed:15639223 ]
  4. Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride. Pharm Res. 2003 Jul;20(7):1093-100. [PubMed:12880296 ]
External Links
ATC CodesB01AA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (64.7 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8724
Blood Brain Barrier+0.8343
Caco-2 permeable-0.5899
P-glycoprotein substrateNon-substrate0.5073
P-glycoprotein inhibitor INon-inhibitor0.9304
P-glycoprotein inhibitor IINon-inhibitor0.8972
Renal organic cation transporterNon-inhibitor0.8982
CYP450 2C9 substrateNon-substrate0.8264
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7557
CYP450 1A2 substrateNon-inhibitor0.7905
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.9681
CYP450 2C19 inhibitorNon-inhibitor0.6071
CYP450 3A4 inhibitorNon-inhibitor0.9098
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9165
Ames testNon AMES toxic0.9048
CarcinogenicityNon-carcinogens0.9549
BiodegradationNot ready biodegradable0.8347
Rat acute toxicity3.1251 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9269
hERG inhibition (predictor II)Non-inhibitor0.9435
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Abbott laboratories pharmaceutical products div
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point290 °CPhysProp
water solubility128 mg/LNot Available
logP2.07HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0662 mg/mLALOGPS
logP1.54ALOGPS
logP-1.6ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)-12ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.19 m3·mol-1ChemAxon
Polarizability32.32 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.73 KB)
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Vitamin-k-epoxide reductase (warfarin-sensitive) activity
Specific Function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K. Vitamin K is required for the gamma-carboxylation of various proteins, including clotting factors, and is required for normal blood coagulation, but also for normal bone development.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular Weight:
18234.3 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Wallin R, Patrick SD, Ballard JO: Vitamin K antagonism of coumarin intoxication in the rat. Thromb Haemost. 1986 Apr 30;55(2):235-9. [PubMed:2424118 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Superoxide dismutase activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular Weight:
30867.405 Da
References
  1. Chen S, Wu K, Zhang D, Sherman M, Knox R, Yang CS: Molecular characterization of binding of substrates and inhibitors to DT-diaphorase: combined approach involving site-directed mutagenesis, inhibitor-binding analysis, and computer modeling. Mol Pharmacol. 1999 Aug;56(2):272-8. [PubMed:10419545 ]
  2. Jaiswal AK: Characterization and partial purification of microsomal NAD(P)H:quinone oxidoreductases. Arch Biochem Biophys. 2000 Mar 1;375(1):62-8. [PubMed:10683249 ]
  3. Joseph P, Jaiswal AK: A unique cytosolic activity related but distinct from NQO1 catalyses metabolic activation of mitomycin C. Br J Cancer. 2000 Apr;82(7):1305-11. [PubMed:10755406 ]
  4. Floreani M, Napoli E, Palatini P: Protective action of cardiac DT-diaphorase against menadione toxicity in guinea pig isolated atria. Biochem Pharmacol. 2000 Aug 15;60(4):601-5. [PubMed:10874136 ]
  5. Arriagada C, Dagnino-Subiabre A, Caviedes P, Armero JM, Caviedes R, Segura-Aguilar J: Studies of aminochrome toxicity in a mouse derived neuronal cell line: is this toxicity mediated via glutamate transmission? Amino Acids. 2000;18(4):363-73. [PubMed:10949919 ]
  6. Preusch PC, Smalley DM: Vitamin K1 2,3-epoxide and quinone reduction: mechanism and inhibition. Free Radic Res Commun. 1990;8(4-6):401-15. [PubMed:2113031 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
Does not have alcohol dehydrogenase activity. Binds NADP and acts through a one-electron transfer process. Orthoquinones, such as 1,2-naphthoquinone or 9,10-phenanthrenequinone, are the best substrates (in vitro). May act in the detoxification of xenobiotics. Interacts with (AU)-rich elements (ARE) in the 3'-UTR of target mRNA species. Enhances the stability of mRNA coding for BCL2. NADPH bindi...
Gene Name:
CRYZ
Uniprot ID:
Q08257
Molecular Weight:
35206.36 Da
References
  1. Evans PJ: Decreased intracellular proteolysis correlates with the maintenance of a specific isoenzyme of cytochrome P-450. Cell Biol Int. 1999;23(2):117-24. [PubMed:10561120 ]
  2. Audi SH, Bongard RD, Dawson CA, Siegel D, Roerig DL, Merker MP: Duroquinone reduction during passage through the pulmonary circulation. Am J Physiol Lung Cell Mol Physiol. 2003 Nov;285(5):L1116-31. Epub 2003 Jul 25. [PubMed:12882764 ]
  3. Asher G, Dym O, Tsvetkov P, Adler J, Shaul Y: The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol. Biochemistry. 2006 May 23;45(20):6372-8. [PubMed:16700548 ]
  4. Maser E, Gebel T, Netter KJ: Carbonyl reduction of metyrapone in human liver. Biochem Pharmacol. 1991 Dec 11;42 Suppl:S93-8. [PubMed:1722672 ]
  5. Hao H, Wang G, Cui N, Li J, Xie L, Ding Z: Identification of a novel intestinal first pass metabolic pathway: NQO1 mediated quinone reduction and subsequent glucuronidation. Curr Drug Metab. 2007 Feb;8(2):137-49. [PubMed:17305492 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 June 13, 2005 07:24 / Updated on August 17, 2016 12:23