You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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 KeyInChIKey=DOBMPNYZJYQDGZ-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
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
Pharmacology
IndicationFor decreasing blood clotting. Often used along with heparin for treatment of deep vein thrombosis.
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.
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
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
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)
Interactions
Drug Interactions
Drug
AbciximabAbciximab may increase the anticoagulant activities of Dicoumarol.
AbirateroneThe metabolism of Dicoumarol can be decreased when combined with Abiraterone.
AceclofenacAceclofenac may increase the anticoagulant activities of Dicoumarol.
AcenocoumarolDicoumarol may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenAcetaminophen may increase the anticoagulant activities of Dicoumarol.
AcetohexamideAcetohexamide may increase the anticoagulant activities of Dicoumarol.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Dicoumarol.
AdapaleneAdapalene may increase the anticoagulant activities of Dicoumarol.
AllopurinolAllopurinol may increase the anticoagulant activities of Dicoumarol.
AllylestrenolThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Allylestrenol.
AlprostadilAlprostadil may increase the anticoagulant activities of Dicoumarol.
AlteplaseAlteplase may increase the anticoagulant activities of Dicoumarol.
AltrenogestThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Altrenogest.
ALX-0081ALX-0081 may increase the anticoagulant activities of Dicoumarol.
AmdinocillinAmdinocillin may increase the anticoagulant activities of Dicoumarol.
AmineptineAmineptine may increase the anticoagulant activities of Dicoumarol.
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Dicoumarol.
AmiodaroneThe metabolism of Dicoumarol can be decreased when combined with Amiodarone.
AmitriptylineAmitriptyline may increase the anticoagulant activities of Dicoumarol.
AmobarbitalThe metabolism of Dicoumarol can be increased when combined with Amobarbital.
AmoxapineAmoxapine may increase the anticoagulant activities of Dicoumarol.
AmoxicillinAmoxicillin may increase the anticoagulant activities of Dicoumarol.
AmpicillinAmpicillin may increase the anticoagulant activities of Dicoumarol.
AnagrelideAnagrelide may increase the anticoagulant activities of Dicoumarol.
AncrodDicoumarol may increase the anticoagulant activities of Ancrod.
AnistreplaseAnistreplase may increase the anticoagulant activities of Dicoumarol.
AntipyrineAntipyrine may increase the anticoagulant activities of Dicoumarol.
Antithrombin III humanDicoumarol may increase the anticoagulant activities of Antithrombin III human.
ApixabanApixaban may increase the anticoagulant activities of Dicoumarol.
ApremilastApremilast may increase the anticoagulant activities of Dicoumarol.
AprepitantThe metabolism of Dicoumarol can be increased when combined with Aprepitant.
AprotininThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Aprotinin.
ArdeparinDicoumarol may increase the anticoagulant activities of Ardeparin.
ArgatrobanDicoumarol may increase the anticoagulant activities of Argatroban.
AstaxanthinAstaxanthin may increase the anticoagulant activities of Dicoumarol.
AtorvastatinAtorvastatin may increase the anticoagulant activities of Dicoumarol.
AzapropazoneAzapropazone may increase the anticoagulant activities of Dicoumarol.
AzathioprineAzathioprine may decrease the anticoagulant activities of Dicoumarol.
AzelastineAzelastine may increase the anticoagulant activities of Dicoumarol.
AzlocillinAzlocillin may increase the anticoagulant activities of Dicoumarol.
BalsalazideBalsalazide may increase the anticoagulant activities of Dicoumarol.
BarbitalThe metabolism of Dicoumarol can be increased when combined with Barbital.
BatroxobinBatroxobin may increase the anticoagulant activities of Dicoumarol.
BazedoxifeneBazedoxifene may decrease the anticoagulant activities of Dicoumarol.
BecaplerminBecaplermin may increase the anticoagulant activities of Dicoumarol.
BemiparinBemiparin may increase the anticoagulant activities of Dicoumarol.
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Dicoumarol.
Benzathine benzylpenicillinBenzathine benzylpenicillin may increase the anticoagulant activities of Dicoumarol.
BenzylpenicillinBenzylpenicillin may increase the anticoagulant activities of Dicoumarol.
Benzylpenicillin PotassiumBenzylpenicillin Potassium may increase the anticoagulant activities of Dicoumarol.
BeraprostBeraprost may increase the anticoagulant activities of Dicoumarol.
BezafibrateBezafibrate may increase the anticoagulant activities of Dicoumarol.
BicalutamideThe serum concentration of Dicoumarol can be increased when it is combined with Bicalutamide.
BivalirudinBivalirudin may increase the anticoagulant activities of Dicoumarol.
BosentanThe metabolism of Dicoumarol can be increased when combined with Bosentan.
BromfenacBromfenac may increase the anticoagulant activities of Dicoumarol.
CangrelorCangrelor may increase the anticoagulant activities of Dicoumarol.
CapecitabineThe serum concentration of Dicoumarol can be increased when it is combined with Capecitabine.
CarbamazepineThe serum concentration of Dicoumarol can be decreased when it is combined with Carbamazepine.
CarbenicillinCarbenicillin may increase the anticoagulant activities of Dicoumarol.
CarbimazoleCarbimazole may decrease the anticoagulant activities of Dicoumarol.
CarprofenCarprofen may increase the anticoagulant activities of Dicoumarol.
CastanospermineCastanospermine may increase the anticoagulant activities of Dicoumarol.
CefacetrileCefacetrile may increase the anticoagulant activities of Dicoumarol.
CefaclorCefaclor may increase the anticoagulant activities of Dicoumarol.
CefadroxilCefadroxil may increase the anticoagulant activities of Dicoumarol.
CefalotinCefalotin may increase the anticoagulant activities of Dicoumarol.
CefamandoleCefamandole may increase the anticoagulant activities of Dicoumarol.
CefapirinCefapirin may increase the anticoagulant activities of Dicoumarol.
CefazolinCefazolin may increase the anticoagulant activities of Dicoumarol.
CefiximeCefixime may increase the anticoagulant activities of Dicoumarol.
CefmenoximeCefmenoxime may increase the anticoagulant activities of Dicoumarol.
CefmetazoleCefmetazole may increase the anticoagulant activities of Dicoumarol.
CefonicidCefonicid may increase the anticoagulant activities of Dicoumarol.
CefoperazoneCefoperazone may increase the anticoagulant activities of Dicoumarol.
CefotaximeCefotaxime may increase the anticoagulant activities of Dicoumarol.
CefotetanCefotetan may increase the anticoagulant activities of Dicoumarol.
CefotiamCefotiam may increase the anticoagulant activities of Dicoumarol.
CefoxitinCefoxitin may increase the anticoagulant activities of Dicoumarol.
CefradineCefradine may increase the anticoagulant activities of Dicoumarol.
CeftazidimeCeftazidime may increase the anticoagulant activities of Dicoumarol.
CeftizoximeCeftizoxime may increase the anticoagulant activities of Dicoumarol.
CeftriaxoneCeftriaxone may increase the anticoagulant activities of Dicoumarol.
CefuroximeCefuroxime may increase the anticoagulant activities of Dicoumarol.
CelecoxibCelecoxib may increase the anticoagulant activities of Dicoumarol.
CephalexinCephalexin may increase the anticoagulant activities of Dicoumarol.
CephaloglycinCephaloglycin may increase the anticoagulant activities of Dicoumarol.
CephaloridineCephaloridine may increase the anticoagulant activities of Dicoumarol.
CeritinibThe serum concentration of Dicoumarol can be increased when it is combined with Ceritinib.
CerivastatinCerivastatin may increase the anticoagulant activities of Dicoumarol.
CertoparinDicoumarol may increase the anticoagulant activities of Certoparin.
Chloral hydrateThe serum concentration of Dicoumarol can be increased when it is combined with Chloral hydrate.
ChloramphenicolChloramphenicol may increase the anticoagulant activities of Dicoumarol.
ChloroquineChloroquine may increase the anticoagulant activities of Dicoumarol.
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Dicoumarol.
ChlorpropamideChlorpropamide may increase the anticoagulant activities of Dicoumarol.
CholecalciferolThe metabolism of Dicoumarol can be decreased when combined with Cholecalciferol.
CholestyramineCholestyramine can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.
CilostazolCilostazol may increase the anticoagulant activities of Dicoumarol.
CimetidineCimetidine may increase the anticoagulant activities of Dicoumarol.
CiprofibrateCiprofibrate may increase the anticoagulant activities of Dicoumarol.
CitalopramCitalopram may increase the anticoagulant activities of Dicoumarol.
Citric AcidDicoumarol may increase the anticoagulant activities of Citric Acid.
ClofibrateClofibrate may increase the anticoagulant activities of Dicoumarol.
ClomipramineClomipramine may increase the anticoagulant activities of Dicoumarol.
ClonixinClonixin may increase the anticoagulant activities of Dicoumarol.
ClopidogrelClopidogrel may increase the anticoagulant activities of Dicoumarol.
ClotrimazoleThe metabolism of Dicoumarol can be decreased when combined with Clotrimazole.
CloxacillinCloxacillin may decrease the anticoagulant activities of Dicoumarol.
Coenzyme Q10Coenzyme Q10 may increase the anticoagulant activities of Dicoumarol.
ColesevelamColesevelam can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Collagenase.
Conjugated Equine EstrogensConjugated Equine Estrogens may decrease the anticoagulant activities of Dicoumarol.
CranberryCranberry may increase the anticoagulant activities of Dicoumarol.
CyclacillinCyclacillin may increase the anticoagulant activities of Dicoumarol.
CyclobenzaprineCyclobenzaprine may increase the anticoagulant activities of Dicoumarol.
CyclosporineThe metabolism of Dicoumarol can be decreased when combined with Cyclosporine.
D-LimoneneD-Limonene may increase the anticoagulant activities of Dicoumarol.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Dicoumarol.
DabrafenibThe serum concentration of Dicoumarol can be decreased when it is combined with Dabrafenib.
DalteparinDicoumarol may increase the anticoagulant activities of Dalteparin.
DanaparoidDicoumarol may increase the anticoagulant activities of Danaparoid.
DapoxetineDapoxetine may increase the anticoagulant activities of Dicoumarol.
DasatinibDasatinib may increase the anticoagulant activities of Dicoumarol.
DeferasiroxThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Deferasirox.
DefibrotideDefibrotide may increase the anticoagulant activities of Dicoumarol.
DelavirdineThe metabolism of Dicoumarol can be decreased when combined with Delavirdine.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Deoxycholic Acid.
DesipramineDesipramine may increase the anticoagulant activities of Dicoumarol.
DesirudinDicoumarol may increase the anticoagulant activities of Desirudin.
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Dicoumarol.
DesogestrelThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Desogestrel.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Dicoumarol.
DexmethylphenidateThe serum concentration of Dicoumarol can be increased when it is combined with Dexmethylphenidate.
DextranDicoumarol may increase the anticoagulant activities of Dextran.
Dextran 40Dicoumarol may increase the anticoagulant activities of Dextran 40.
Dextran 70Dicoumarol may increase the anticoagulant activities of Dextran 70.
Dextran 75Dicoumarol may increase the anticoagulant activities of Dextran 75.
DiclofenacDiclofenac may increase the anticoagulant activities of Dicoumarol.
DicloxacillinDicloxacillin may decrease the anticoagulant activities of Dicoumarol.
DienestrolDienestrol may decrease the anticoagulant activities of Dicoumarol.
DienogestThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Dienogest.
DiethylstilbestrolDiethylstilbestrol may decrease the anticoagulant activities of Dicoumarol.
DiflunisalDiflunisal may increase the anticoagulant activities of Dicoumarol.
DihydrotestosteroneDihydrotestosterone may increase the anticoagulant activities of Dicoumarol.
DipyridamoleDipyridamole may increase the anticoagulant activities of Dicoumarol.
DisulfiramThe serum concentration of Dicoumarol can be increased when it is combined with Disulfiram.
DitazoleDitazole may increase the anticoagulant activities of Dicoumarol.
DosulepinDosulepin may increase the anticoagulant activities of Dicoumarol.
DoxepinDoxepin may increase the anticoagulant activities of Dicoumarol.
DronedaroneThe serum concentration of Dicoumarol can be increased when it is combined with Dronedarone.
DrospirenoneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Drospirenone.
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Dicoumarol.
DroxicamDroxicam may increase the anticoagulant activities of Dicoumarol.
DydrogesteroneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Dydrogesterone.
EconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Econazole.
Edetic AcidDicoumarol may increase the anticoagulant activities of Edetic Acid.
EdoxabanEdoxaban may increase the anticoagulant activities of Dicoumarol.
EfavirenzThe serum concentration of Dicoumarol can be decreased when it is combined with Efavirenz.
EnoxaparinDicoumarol may increase the anticoagulant activities of Enoxaparin.
EpinastineEpinastine may increase the anticoagulant activities of Dicoumarol.
EpirizoleEpirizole may increase the anticoagulant activities of Dicoumarol.
EpoprostenolEpoprostenol may increase the anticoagulant activities of Dicoumarol.
EpoprostenolThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Epoprostenol.
EptifibatideEptifibatide may increase the anticoagulant activities of Dicoumarol.
ErythromycinThe serum concentration of Dicoumarol can be increased when it is combined with Erythromycin.
EscitalopramEscitalopram may increase the anticoagulant activities of Dicoumarol.
EsmirtazapineEsmirtazapine may increase the anticoagulant activities of Dicoumarol.
EsomeprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Esomeprazole.
EstradiolEstradiol may decrease the anticoagulant activities of Dicoumarol.
EstriolEstriol may decrease the anticoagulant activities of Dicoumarol.
EstroneEstrone may decrease the anticoagulant activities of Dicoumarol.
Etacrynic acidThe serum concentration of Dicoumarol can be increased when it is combined with Etacrynic acid.
EtanerceptEtanercept may increase the anticoagulant activities of Dicoumarol.
EthanolThe serum concentration of Dicoumarol can be decreased when it is combined with Ethanol.
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Dicoumarol.
EthotoinEthotoin may increase the anticoagulant activities of Dicoumarol.
Ethyl biscoumacetateDicoumarol may increase the anticoagulant activities of Ethyl biscoumacetate.
EtodolacEtodolac may increase the anticoagulant activities of Dicoumarol.
EtofenamateEtofenamate may increase the anticoagulant activities of Dicoumarol.
EtofibrateEtofibrate may increase the anticoagulant activities of Dicoumarol.
EtonogestrelThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Etonogestrel.
EtoperidoneEtoperidone may increase the anticoagulant activities of Dicoumarol.
EtoposideEtoposide may increase the anticoagulant activities of Dicoumarol.
EtoricoxibEtoricoxib may increase the anticoagulant activities of Dicoumarol.
EtravirineThe metabolism of Dicoumarol can be decreased when combined with Etravirine.
Evening primrose oilEvening primrose oil may increase the anticoagulant activities of Dicoumarol.
ExenatideExenatide may increase the anticoagulant activities of Dicoumarol.
exisulindexisulind may increase the anticoagulant activities of Dicoumarol.
FenbufenFenbufen may increase the anticoagulant activities of Dicoumarol.
FenfluramineFenfluramine may increase the anticoagulant activities of Dicoumarol.
FenofibrateFenofibrate may increase the anticoagulant activities of Dicoumarol.
FenoprofenFenoprofen may increase the anticoagulant activities of Dicoumarol.
FibrinolysinFibrinolysin may increase the anticoagulant activities of Dicoumarol.
FloctafenineFloctafenine may increase the anticoagulant activities of Dicoumarol.
FloxuridineThe metabolism of Dicoumarol can be decreased when combined with Floxuridine.
FlucloxacillinFlucloxacillin may increase the anticoagulant activities of Dicoumarol.
FluconazoleThe metabolism of Dicoumarol can be decreased when combined with Fluconazole.
FlunixinFlunixin may increase the anticoagulant activities of Dicoumarol.
FluorouracilThe serum concentration of Dicoumarol can be increased when it is combined with Fluorouracil.
FluoxetineFluoxetine may increase the anticoagulant activities of Dicoumarol.
FluoxymesteroneFluoxymesterone may increase the anticoagulant activities of Dicoumarol.
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Dicoumarol.
FluvastatinFluvastatin may increase the anticoagulant activities of Dicoumarol.
FluvoxamineFluvoxamine may increase the anticoagulant activities of Dicoumarol.
Fondaparinux sodiumDicoumarol may increase the anticoagulant activities of Fondaparinux sodium.
FosphenytoinFosphenytoin may increase the anticoagulant activities of Dicoumarol.
Fusidic AcidThe serum concentration of Dicoumarol can be increased when it is combined with Fusidic Acid.
GefitinibGefitinib may increase the anticoagulant activities of Dicoumarol.
GemfibrozilGemfibrozil may increase the anticoagulant activities of Dicoumarol.
GenisteinGenistein may decrease the anticoagulant activities of Dicoumarol.
GestodeneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Gestodene.
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Ginkgo biloba is combined with Dicoumarol.
GlibornurideGlibornuride may increase the anticoagulant activities of Dicoumarol.
GliclazideGliclazide may increase the anticoagulant activities of Dicoumarol.
GlimepirideGlimepiride may increase the anticoagulant activities of Dicoumarol.
GlipizideGlipizide may increase the anticoagulant activities of Dicoumarol.
GliquidoneGliquidone may increase the anticoagulant activities of Dicoumarol.
GlisoxepideGlisoxepide may increase the anticoagulant activities of Dicoumarol.
Glucagon recombinantGlucagon recombinant may increase the anticoagulant activities of Dicoumarol.
GlutethimideThe metabolism of Dicoumarol can be increased when combined with Glutethimide.
GlyburideGlyburide may increase the anticoagulant activities of Dicoumarol.
GriseofulvinThe serum concentration of Dicoumarol can be decreased when it is combined with Griseofulvin.
HeminHemin may increase the anticoagulant activities of Dicoumarol.
HeparinDicoumarol may increase the anticoagulant activities of Heparin.
HexestrolHexestrol may decrease the anticoagulant activities of Dicoumarol.
HexobarbitalThe metabolism of Dicoumarol can be increased when combined with Hexobarbital.
HirulogDicoumarol may increase the anticoagulant activities of Hirulog.
HMPL-004HMPL-004 may increase the anticoagulant activities of Dicoumarol.
Hydroxyprogesterone caproateThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Hydroxyprogesterone caproate.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Ibritumomab tiuxetan.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dicoumarol.
IbudilastIbudilast may increase the anticoagulant activities of Dicoumarol.
IbuprofenIbuprofen may increase the anticoagulant activities of Dicoumarol.
IbuproxamIbuproxam may increase the anticoagulant activities of Dicoumarol.
IcatibantIcatibant may increase the anticoagulant activities of Dicoumarol.
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Dicoumarol.
IfenprodilIfenprodil may increase the anticoagulant activities of Dicoumarol.
IfosfamideIfosfamide may increase the anticoagulant activities of Dicoumarol.
IloprostIloprost may increase the anticoagulant activities of Dicoumarol.
IloprostThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Iloprost.
ImipramineImipramine may increase the anticoagulant activities of Dicoumarol.
IndalpineIndalpine may increase the anticoagulant activities of Dicoumarol.
IndinavirThe metabolism of Dicoumarol can be decreased when combined with Indinavir.
IndomethacinIndomethacin may increase the anticoagulant activities of Dicoumarol.
IndoprofenIndoprofen may increase the anticoagulant activities of Dicoumarol.
IrbesartanThe metabolism of Dicoumarol can be decreased when combined with Irbesartan.
IsoxicamIsoxicam may increase the anticoagulant activities of Dicoumarol.
ItraconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Itraconazole.
IvermectinIvermectin may increase the anticoagulant activities of Dicoumarol.
KebuzoneKebuzone may increase the anticoagulant activities of Dicoumarol.
KetoconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Ketoconazole.
KetoprofenKetoprofen may increase the anticoagulant activities of Dicoumarol.
KetorolacKetorolac may increase the anticoagulant activities of Dicoumarol.
L-CarnitineL-Carnitine may increase the anticoagulant activities of Dicoumarol.
LansoprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Lansoprazole.
LeflunomideLeflunomide may increase the anticoagulant activities of Dicoumarol.
LepirudinLepirudin may increase the anticoagulant activities of Dicoumarol.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Dicoumarol.
LevonorgestrelThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Levonorgestrel.
LevothyroxineLevothyroxine may increase the anticoagulant activities of Dicoumarol.
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Dicoumarol.
LiothyronineLiothyronine may increase the anticoagulant activities of Dicoumarol.
LiotrixLiotrix may increase the anticoagulant activities of Dicoumarol.
LixisenatideLixisenatide can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.
LornoxicamLornoxicam may increase the anticoagulant activities of Dicoumarol.
LosartanThe metabolism of Dicoumarol can be decreased when combined with Losartan.
LovastatinLovastatin may increase the anticoagulant activities of Dicoumarol.
LoxoprofenLoxoprofen may increase the anticoagulant activities of Dicoumarol.
Lu AA21004Lu AA21004 may increase the anticoagulant activities of Dicoumarol.
LumacaftorThe serum concentration of Dicoumarol can be decreased when it is combined with Lumacaftor.
LumiracoxibLumiracoxib may increase the anticoagulant activities of Dicoumarol.
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Dicoumarol.
MasoprocolMasoprocol may increase the anticoagulant activities of Dicoumarol.
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Dicoumarol.
MedrogestoneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Medrogestone.
Medroxyprogesterone acetateThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Medroxyprogesterone acetate.
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Dicoumarol.
Megestrol acetateThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Megestrol acetate.
MeloxicamMeloxicam may increase the anticoagulant activities of Dicoumarol.
MercaptopurineMercaptopurine may decrease the anticoagulant activities of Dicoumarol.
MesalazineMesalazine may increase the anticoagulant activities of Dicoumarol.
MestranolMestranol may decrease the anticoagulant activities of Dicoumarol.
MetamizoleMetamizole may increase the anticoagulant activities of Dicoumarol.
MethimazoleMethimazole may decrease the anticoagulant activities of Dicoumarol.
MethohexitalThe metabolism of Dicoumarol can be increased when combined with Methohexital.
MethylphenidateThe serum concentration of Dicoumarol can be increased when it is combined with Methylphenidate.
MethylphenobarbitalThe metabolism of Dicoumarol can be increased when combined with Methylphenobarbital.
MethyltestosteroneMethyltestosterone may increase the anticoagulant activities of Dicoumarol.
MeticillinMeticillin may increase the anticoagulant activities of Dicoumarol.
MetronidazoleThe serum concentration of Dicoumarol can be increased when it is combined with Metronidazole.
MevastatinMevastatin may increase the anticoagulant activities of Dicoumarol.
MezlocillinMezlocillin may increase the anticoagulant activities of Dicoumarol.
MiconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Miconazole.
MifepristoneThe serum concentration of Dicoumarol can be increased when it is combined with Mifepristone.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Dicoumarol.
MilrinoneMilrinone may increase the anticoagulant activities of Dicoumarol.
MirtazapineMirtazapine may increase the anticoagulant activities of Dicoumarol.
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Dicoumarol.
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Dicoumarol.
NabumetoneNabumetone may increase the anticoagulant activities of Dicoumarol.
NadroparinDicoumarol may increase the anticoagulant activities of Nadroparin.
NafcillinNafcillin may increase the anticoagulant activities of Dicoumarol.
NaftifineNaftifine may increase the anticoagulant activities of Dicoumarol.
NaproxenNaproxen may increase the anticoagulant activities of Dicoumarol.
NCX 4016NCX 4016 may increase the anticoagulant activities of Dicoumarol.
NeomycinNeomycin may increase the anticoagulant activities of Dicoumarol.
NepafenacNepafenac may increase the anticoagulant activities of Dicoumarol.
NicardipineThe metabolism of Dicoumarol can be decreased when combined with Nicardipine.
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Dicoumarol.
NimesulideNimesulide may increase the anticoagulant activities of Dicoumarol.
NintedanibThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Nintedanib.
NorethisteroneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Norethisterone.
NortriptylineNortriptyline may increase the anticoagulant activities of Dicoumarol.
ObinutuzumabThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Obinutuzumab.
OlanzapineOlanzapine may increase the anticoagulant activities of Dicoumarol.
OlopatadineOlopatadine may increase the anticoagulant activities of Dicoumarol.
OlsalazineOlsalazine may increase the anticoagulant activities of Dicoumarol.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Omacetaxine mepesuccinate.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Dicoumarol.
OmeprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Omeprazole.
OrgoteinOrgotein may increase the anticoagulant activities of Dicoumarol.
OritavancinThe serum concentration of Dicoumarol can be increased when it is combined with Oritavancin.
OtamixabanDicoumarol may increase the anticoagulant activities of Otamixaban.
OxacillinOxacillin may increase the anticoagulant activities of Dicoumarol.
OxandroloneOxandrolone may increase the anticoagulant activities of Dicoumarol.
OxaprozinOxaprozin may increase the anticoagulant activities of Dicoumarol.
OxymetholoneOxymetholone may increase the anticoagulant activities of Dicoumarol.
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Dicoumarol.
ParecoxibParecoxib may increase the anticoagulant activities of Dicoumarol.
ParnaparinParnaparin may increase the anticoagulant activities of Dicoumarol.
ParoxetineParoxetine may increase the anticoagulant activities of Dicoumarol.
PentobarbitalThe metabolism of Dicoumarol can be increased when combined with Pentobarbital.
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Dicoumarol.
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Dicoumarol.
PhenindioneDicoumarol may increase the anticoagulant activities of Phenindione.
PhenobarbitalThe metabolism of Dicoumarol can be increased when combined with Phenobarbital.
PhenoxymethylpenicillinPhenoxymethylpenicillin may increase the anticoagulant activities of Dicoumarol.
PhenprocoumonDicoumarol may increase the anticoagulant activities of Phenprocoumon.
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Dicoumarol.
PhenytoinPhenytoin may increase the anticoagulant activities of Dicoumarol.
PhylloquinonePhylloquinone may decrease the anticoagulant activities of Dicoumarol.
PimecrolimusPimecrolimus may increase the anticoagulant activities of Dicoumarol.
PiperacillinPiperacillin may increase the anticoagulant activities of Dicoumarol.
PirfenidonePirfenidone may increase the anticoagulant activities of Dicoumarol.
PiroxicamPiroxicam may increase the anticoagulant activities of Dicoumarol.
PitavastatinPitavastatin may increase the anticoagulant activities of Dicoumarol.
PivampicillinPivampicillin may increase the anticoagulant activities of Dicoumarol.
PivmecillinamPivmecillinam may increase the anticoagulant activities of Dicoumarol.
PlasminPlasmin may increase the anticoagulant activities of Dicoumarol.
Polyestradiol phosphatePolyestradiol phosphate may decrease the anticoagulant activities of Dicoumarol.
PosaconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Posaconazole.
PrasugrelPrasugrel may increase the anticoagulant activities of Dicoumarol.
PravastatinPravastatin may increase the anticoagulant activities of Dicoumarol.
PrimidoneThe metabolism of Dicoumarol can be increased when combined with Primidone.
Procaine benzylpenicillinProcaine benzylpenicillin may increase the anticoagulant activities of Dicoumarol.
ProgesteroneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Progesterone.
PropacetamolPropacetamol may increase the anticoagulant activities of Dicoumarol.
PropafenoneThe serum concentration of Dicoumarol can be increased when it is combined with Propafenone.
PropylthiouracilPropylthiouracil may decrease the anticoagulant activities of Dicoumarol.
Protein CDicoumarol may increase the anticoagulant activities of Protein C.
ProtocatechualdehydeDicoumarol may increase the anticoagulant activities of Protocatechualdehyde.
ProtriptylineProtriptyline may increase the anticoagulant activities of Dicoumarol.
PTC299PTC299 may increase the anticoagulant activities of Dicoumarol.
PyrimethamineThe metabolism of Dicoumarol can be decreased when combined with Pyrimethamine.
QuinestrolQuinestrol may decrease the anticoagulant activities of Dicoumarol.
QuinidineQuinidine may increase the anticoagulant activities of Dicoumarol.
QuinineQuinine may increase the anticoagulant activities of Dicoumarol.
ResveratrolResveratrol may increase the anticoagulant activities of Dicoumarol.
ReteplaseReteplase may increase the anticoagulant activities of Dicoumarol.
ReviparinDicoumarol may increase the anticoagulant activities of Reviparin.
RidogrelRidogrel may increase the anticoagulant activities of Dicoumarol.
RifampicinThe metabolism of Dicoumarol can be increased when combined with Rifampicin.
RifapentineThe metabolism of Dicoumarol can be increased when combined with Rifapentine.
RivaroxabanDicoumarol may increase the anticoagulant activities of Rivaroxaban.
RofecoxibRofecoxib may increase the anticoagulant activities of Dicoumarol.
RosiglitazoneRosiglitazone may increase the anticoagulant activities of Dicoumarol.
RosuvastatinRosuvastatin may increase the anticoagulant activities of Dicoumarol.
SalicylamideSalicylamide may increase the anticoagulant activities of Dicoumarol.
Salicylic acidSalicylic acid may increase the anticoagulant activities of Dicoumarol.
SalsalateSalsalate may increase the anticoagulant activities of Dicoumarol.
SCH-530348SCH-530348 may increase the anticoagulant activities of Dicoumarol.
SecobarbitalThe metabolism of Dicoumarol can be increased when combined with Secobarbital.
SelexipagSelexipag may increase the anticoagulant activities of Dicoumarol.
SeratrodastSeratrodast may increase the anticoagulant activities of Dicoumarol.
SertralineSertraline may increase the anticoagulant activities of Dicoumarol.
SevofluraneSevoflurane may increase the anticoagulant activities of Dicoumarol.
SildenafilThe metabolism of Dicoumarol can be decreased when combined with Sildenafil.
SimvastatinSimvastatin may increase the anticoagulant activities of Dicoumarol.
SorafenibThe metabolism of Dicoumarol can be decreased when combined with Sorafenib.
SRT501SRT501 may increase the anticoagulant activities of Dicoumarol.
St. John's WortThe metabolism of Dicoumarol can be increased when combined with St. John's Wort.
StanozololStanozolol may increase the anticoagulant activities of Dicoumarol.
StreptokinaseStreptokinase may increase the anticoagulant activities of Dicoumarol.
SucralfateSucralfate may decrease the anticoagulant activities of Dicoumarol.
SugammadexSugammadex may increase the anticoagulant activities of Dicoumarol.
SulbactamSulbactam may increase the anticoagulant activities of Dicoumarol.
SulfadiazineSulfadiazine may increase the anticoagulant activities of Dicoumarol.
SulfamethoxazoleThe metabolism of Dicoumarol can be decreased when combined with Sulfamethoxazole.
SulfasalazineSulfasalazine may increase the anticoagulant activities of Dicoumarol.
SulfinpyrazoneThe metabolism of Dicoumarol can be decreased when combined with Sulfinpyrazone.
SulfisoxazoleSulfisoxazole may increase the anticoagulant activities of Dicoumarol.
SulindacSulindac may increase the anticoagulant activities of Dicoumarol.
SulodexideDicoumarol may increase the anticoagulant activities of Sulodexide.
SuprofenSuprofen may increase the anticoagulant activities of Dicoumarol.
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Dicoumarol.
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Dicoumarol.
TamoxifenThe serum concentration of Dicoumarol can be increased when it is combined with Tamoxifen.
TegafurThe serum concentration of Dicoumarol can be increased when it is combined with Tegafur.
TenecteplaseTenecteplase may increase the anticoagulant activities of Dicoumarol.
TenoxicamTenoxicam may increase the anticoagulant activities of Dicoumarol.
TepoxalinTepoxalin may increase the anticoagulant activities of Dicoumarol.
TeriflunomideTeriflunomide may increase the anticoagulant activities of Dicoumarol.
TesmilifeneTesmilifene may increase the anticoagulant activities of Dicoumarol.
TestosteroneTestosterone may increase the anticoagulant activities of Dicoumarol.
ThiamylalThe metabolism of Dicoumarol can be increased when combined with Thiamylal.
ThiopentalThe metabolism of Dicoumarol can be increased when combined with Thiopental.
Thyroid, porcineThyroid, porcine may increase the anticoagulant activities of Dicoumarol.
TianeptineTianeptine may increase the anticoagulant activities of Dicoumarol.
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Dicoumarol.
TiboloneTibolone may increase the anticoagulant activities of Dicoumarol.
TicagrelorTicagrelor may increase the anticoagulant activities of Dicoumarol.
TicarcillinTicarcillin may increase the anticoagulant activities of Dicoumarol.
TiclopidineTiclopidine may increase the anticoagulant activities of Dicoumarol.
TinzaparinTinzaparin may increase the anticoagulant activities of Dicoumarol.
TipranavirTipranavir may increase the anticoagulant activities of Dicoumarol.
TirofibanTirofiban may increase the anticoagulant activities of Dicoumarol.
TolazamideTolazamide may increase the anticoagulant activities of Dicoumarol.
TolbutamideTolbutamide may increase the anticoagulant activities of Dicoumarol.
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Dicoumarol.
TolmetinTolmetin may increase the anticoagulant activities of Dicoumarol.
ToremifeneToremifene may increase the anticoagulant activities of Dicoumarol.
TositumomabThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Tositumomab.
TramadolTramadol may increase the anticoagulant activities of Dicoumarol.
TranilastTranilast may increase the anticoagulant activities of Dicoumarol.
TrapidilTrapidil may increase the anticoagulant activities of Dicoumarol.
TrazodoneTrazodone may increase the anticoagulant activities of Dicoumarol.
TreprostinilTreprostinil may increase the anticoagulant activities of Dicoumarol.
TreprostinilThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Treprostinil.
TriflusalTriflusal may increase the anticoagulant activities of Dicoumarol.
TrimethoprimThe metabolism of Dicoumarol can be decreased when combined with Trimethoprim.
TrimipramineTrimipramine may increase the anticoagulant activities of Dicoumarol.
Trisalicylate-cholineTrisalicylate-choline may increase the anticoagulant activities of Dicoumarol.
UrokinaseUrokinase may increase the anticoagulant activities of Dicoumarol.
ValdecoxibValdecoxib may increase the anticoagulant activities of Dicoumarol.
Valproic AcidThe metabolism of Dicoumarol can be decreased when combined with Valproic Acid.
ValsartanThe metabolism of Dicoumarol can be decreased when combined with Valsartan.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Dicoumarol.
VilazodoneVilazodone may increase the anticoagulant activities of Dicoumarol.
Vitamin EVitamin E may increase the anticoagulant activities of Dicoumarol.
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Dicoumarol.
VoriconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Voriconazole.
VorinostatVorinostat may increase the anticoagulant activities of Dicoumarol.
VortioxetineVortioxetine may increase the anticoagulant activities of Dicoumarol.
WarfarinDicoumarol may increase the anticoagulant activities of Warfarin.
XimelagatranDicoumarol may increase the anticoagulant activities of Ximelagatran.
ZafirlukastThe serum concentration of Dicoumarol can be increased when it is combined with Zafirlukast.
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Dicoumarol.
ZeranolZeranol may decrease the anticoagulant activities of Dicoumarol.
ZileutonZileuton may increase the anticoagulant activities of Dicoumarol.
ZimelidineZimelidine may increase the anticoagulant activities of Dicoumarol.
ZomepiracZomepirac may increase the anticoagulant activities of Dicoumarol.
Food InteractionsNot Available

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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23