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Identification
NameDicoumarol
Accession NumberDB00266  (APRD00761)
TypeSmall Molecule
GroupsApproved
Description

An 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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot 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.
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
PathwaysNot Available
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)
SpectraNot 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
  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
  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
  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
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.
AcenocoumarolDicoumarol may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenAcetaminophen may increase the anticoagulant activities of Dicoumarol.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Dicoumarol.
AllopurinolAllopurinol may increase the anticoagulant activities of Dicoumarol.
AlteplaseAlteplase may increase the anticoagulant activities of Dicoumarol.
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Dicoumarol.
AmiodaroneAmiodarone may increase the anticoagulant activities of Dicoumarol.
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.
ApixabanApixaban may increase the anticoagulant activities of Dicoumarol.
ArgatrobanDicoumarol may increase the anticoagulant activities of Argatroban.
AvibactamAvibactam may increase the anticoagulant activities of Dicoumarol.
AzathioprineAzathioprine may decrease the anticoagulant activities of Dicoumarol.
AzithromycinThe serum concentration of Dicoumarol can be increased when it is combined with Azithromycin.
Benzathine benzylpenicillinBenzathine benzylpenicillin 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.
BiotinBiotin may increase the anticoagulant activities of Dicoumarol.
Bismuth SubsalicylateBismuth Subsalicylate may increase the anticoagulant activities of Dicoumarol.
BivalirudinDicoumarol may increase the anticoagulant activities of Bivalirudin.
BosentanThe metabolism of Dicoumarol can be increased when combined with Bosentan.
ButabarbitalThe metabolism of Dicoumarol can be increased when combined with Butabarbital.
ButalbitalThe metabolism of Dicoumarol can be increased when combined with Butalbital.
CaffeineCaffeine 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.
CefaclorCefaclor may increase the anticoagulant activities of Dicoumarol.
CefadroxilCefadroxil may increase the anticoagulant activities of Dicoumarol.
CefazolinCefazolin may increase the anticoagulant activities of Dicoumarol.
CefdinirCefdinir may increase the anticoagulant activities of Dicoumarol.
CefditorenCefditoren may increase the anticoagulant activities of Dicoumarol.
CefiximeCefixime may increase the anticoagulant activities of Dicoumarol.
CefotaximeCefotaxime may increase the anticoagulant activities of Dicoumarol.
CefotetanCefotetan may increase the anticoagulant activities of Dicoumarol.
CefoxitinCefoxitin may increase the anticoagulant activities of Dicoumarol.
CefpodoximeCefpodoxime may increase the anticoagulant activities of Dicoumarol.
CefprozilCefprozil may increase the anticoagulant activities of Dicoumarol.
Ceftaroline fosamilCeftaroline fosamil may increase the anticoagulant activities of Dicoumarol.
CeftazidimeCeftazidime may increase the anticoagulant activities of Dicoumarol.
CeftibutenCeftibuten may increase the anticoagulant activities of Dicoumarol.
CeftolozaneCeftolozane 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.
ChloramphenicolChloramphenicol may increase the anticoagulant activities of Dicoumarol.
ChlorpropamideChlorpropamide may increase the anticoagulant activities of Dicoumarol.
CholestyramineCholestyramine can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.
Choline fenofibrateCholine fenofibrate may increase the anticoagulant activities of Dicoumarol.
CilostazolCilostazol may increase the anticoagulant activities of Dicoumarol.
CimetidineCimetidine may increase the anticoagulant activities of Dicoumarol.
CiprofloxacinCiprofloxacin may increase the anticoagulant activities of Dicoumarol.
CitalopramCitalopram may increase the anticoagulant activities of Dicoumarol.
ClarithromycinThe serum concentration of Dicoumarol can be increased when it is combined with Clarithromycin.
ClavulanateClavulanate may increase the anticoagulant activities of Dicoumarol.
ClomipramineClomipramine may increase the anticoagulant activities of Dicoumarol.
ClopidogrelClopidogrel may increase the anticoagulant activities of Dicoumarol.
CloxacillinCloxacillin may decrease 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.
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Collagenase clostridium histolyticum.
Cyproterone acetateThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Cyproterone acetate.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Dicoumarol.
DalteparinDicoumarol may increase the anticoagulant activities of Dalteparin.
DanaparoidDicoumarol may increase the anticoagulant activities of Danaparoid.
DanazolDanazol 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.
DemeclocyclineDemeclocycline may increase the anticoagulant activities of Dicoumarol.
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.
DesogestrelDesogestrel may decrease the anticoagulant activities of Dicoumarol.
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.
DiclofenacDiclofenac may increase the anticoagulant activities of Dicoumarol.
DicloxacillinDicloxacillin may decrease the anticoagulant activities of Dicoumarol.
DienogestDienogest may decrease the anticoagulant activities of Dicoumarol.
DiflunisalDiflunisal may increase the anticoagulant activities of Dicoumarol.
DihydrocodeineDihydrocodeine 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.
DoxepinDoxepin may increase the anticoagulant activities of Dicoumarol.
DoxycyclineDoxycycline may increase the anticoagulant activities of Dicoumarol.
DronedaroneThe serum concentration of Dicoumarol can be increased when it is combined with Dronedarone.
DrospirenoneDrospirenone may decrease the anticoagulant activities of Dicoumarol.
DuloxetineDuloxetine may increase the anticoagulant activities of Dicoumarol.
EconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Econazole.
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.
EpoprostenolThe risk or severity of adverse effects can be increased when Epoprostenol is combined with Dicoumarol.
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.
EsomeprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Esomeprazole.
EstradiolEstradiol may decrease the anticoagulant activities of Dicoumarol.
EstropipateEstropipate may decrease the anticoagulant activities of Dicoumarol.
Ethacrynic acidThe serum concentration of Dicoumarol can be increased when it is combined with Ethacrynic acid.
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Dicoumarol.
EthotoinEthotoin may increase the anticoagulant activities of Dicoumarol.
EthynodiolEthynodiol may decrease the anticoagulant activities of Dicoumarol.
EtodolacEtodolac may increase the anticoagulant activities of Dicoumarol.
EtonogestrelEtonogestrel may decrease the anticoagulant activities of Dicoumarol.
EtoposideEtoposide may increase the anticoagulant activities of Dicoumarol.
ExenatideExenatide may increase the anticoagulant activities of Dicoumarol.
FenofibrateFenofibrate may increase the anticoagulant activities of Dicoumarol.
FenoprofenFenoprofen may increase the anticoagulant activities of Dicoumarol.
FloctafenineFloctafenine may increase the anticoagulant activities of Dicoumarol.
FluconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Fluconazole.
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.
GefitinibGefitinib may increase the anticoagulant activities of Dicoumarol.
GemfibrozilGemfibrozil may increase the anticoagulant activities of Dicoumarol.
GemifloxacinGemifloxacin 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.
GlyburideGlyburide may increase the anticoagulant activities of Dicoumarol.
GriseofulvinThe serum concentration of Dicoumarol can be decreased when it is combined with Griseofulvin.
HeparinDicoumarol may increase the anticoagulant activities of Heparin.
Hydroxyprogesterone caproateThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Hydroxyprogesterone caproate.
IbritumomabThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dicoumarol.
IbuprofenIbuprofen may increase the anticoagulant activities of Dicoumarol.
IcosapentIcosapent may increase the anticoagulant activities of Dicoumarol.
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Dicoumarol.
IfosfamideIfosfamide may increase the anticoagulant activities of Dicoumarol.
IloprostThe risk or severity of adverse effects can be increased when Iloprost is combined with Dicoumarol.
ImipramineImipramine may increase the anticoagulant activities of Dicoumarol.
IndomethacinIndomethacin may increase the anticoagulant activities of Dicoumarol.
IsomethepteneIsometheptene 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.
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.
LevofloxacinLevofloxacin may increase the anticoagulant activities of Dicoumarol.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Dicoumarol.
LevonorgestrelLevonorgestrel may decrease the anticoagulant activities of Dicoumarol.
LevothyroxineLevothyroxine may increase the anticoagulant activities of Dicoumarol.
LiothyronineLiothyronine may increase the anticoagulant activities of Dicoumarol.
LiotrixLiotrix may increase the anticoagulant activities of Dicoumarol.
LovastatinLovastatin may increase the anticoagulant activities of Dicoumarol.
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Dicoumarol.
Medroxyprogesterone AcetateMedroxyprogesterone Acetate may decrease the anticoagulant activities of Dicoumarol.
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.
MestranolMestranol may decrease 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.
MethyltestosteroneMethyltestosterone may increase the anticoagulant activities of Dicoumarol.
MetronidazoleThe serum concentration of Dicoumarol can be increased when it is combined with Metronidazole.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Dicoumarol.
MinocyclineMinocycline may increase the anticoagulant activities of Dicoumarol.
MoxifloxacinMoxifloxacin 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 decrease the anticoagulant activities of Dicoumarol.
NaproxenNaproxen may increase the anticoagulant activities of Dicoumarol.
NeomycinNeomycin may increase the anticoagulant activities of Dicoumarol.
NintedanibThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Nintedanib.
NorethindroneNorethindrone may decrease the anticoagulant activities of Dicoumarol.
NorfloxacinNorfloxacin may increase the anticoagulant activities of Dicoumarol.
NorgestimateNorgestimate may decrease the anticoagulant activities of Dicoumarol.
NortriptylineNortriptyline may increase the anticoagulant activities of Dicoumarol.
ObinutuzumabThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Obinutuzumab.
OfloxacinOfloxacin may increase the anticoagulant activities of Dicoumarol.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Dicoumarol.
Omega-3-acid ethyl estersOmega-3-acid ethyl esters may increase the anticoagulant activities of Dicoumarol.
OmeprazoleThe serum concentration of Dicoumarol can be increased when it is combined with Omeprazole.
OritavancinThe serum concentration of Dicoumarol can be increased when it is combined with Oritavancin.
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.
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.
PhenobarbitalThe metabolism of Dicoumarol can be increased when combined with Phenobarbital.
PhenytoinPhenytoin may increase the anticoagulant activities of Dicoumarol.
PhylloquinonePhylloquinone may decrease the anticoagulant activities of Dicoumarol.
PiperacillinPiperacillin may increase the anticoagulant activities of Dicoumarol.
PiroxicamPiroxicam may increase the anticoagulant activities of Dicoumarol.
PitavastatinPitavastatin may increase the anticoagulant activities of Dicoumarol.
PosaconazoleThe serum concentration of Dicoumarol can be increased when it is combined with Posaconazole.
Potassium IodidePotassium Iodide may decrease the anticoagulant activities of Dicoumarol.
PrasugrelPrasugrel may increase the anticoagulant activities of Dicoumarol.
PravastatinPravastatin may increase the anticoagulant activities of Dicoumarol.
Procaine benzylpenicillinProcaine benzylpenicillin may increase the anticoagulant activities of Dicoumarol.
ProgesteroneThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Progesterone.
PropafenoneThe serum concentration of Dicoumarol can be increased when it is combined with Propafenone.
PropylthiouracilPropylthiouracil may decrease the anticoagulant activities of Dicoumarol.
ProtriptylineProtriptyline may increase the anticoagulant activities of Dicoumarol.
QuinidineQuinidine may increase the anticoagulant activities of Dicoumarol.
QuinineQuinine may increase the anticoagulant activities of Dicoumarol.
ReteplaseReteplase may increase the anticoagulant activities of Dicoumarol.
RifabutinThe metabolism of Dicoumarol can be increased when combined with Rifabutin.
RivaroxabanDicoumarol may increase the anticoagulant activities of Rivaroxaban.
RosuvastatinRosuvastatin may increase the anticoagulant activities of Dicoumarol.
SalsalateSalsalate may increase the anticoagulant activities of Dicoumarol.
SecobarbitalThe metabolism of Dicoumarol can be increased when combined with Secobarbital.
SertralineSertraline may increase the anticoagulant activities of Dicoumarol.
SimvastatinSimvastatin may increase the anticoagulant activities of Dicoumarol.
SucralfateSucralfate may decrease the anticoagulant activities of Dicoumarol.
SulfadiazineSulfadiazine may increase the anticoagulant activities of Dicoumarol.
SulfamethoxazoleSulfamethoxazole may increase the anticoagulant activities of Dicoumarol.
SulfisoxazoleSulfisoxazole may increase the anticoagulant activities of Dicoumarol.
SulindacSulindac may increase the anticoagulant activities of Dicoumarol.
TamoxifenThe serum concentration of Dicoumarol can be increased when it is combined with Tamoxifen.
TazobactamTazobactam may increase the anticoagulant activities of Dicoumarol.
TelithromycinThe serum concentration of Dicoumarol can be increased when it is combined with Telithromycin.
TenecteplaseTenecteplase may increase the anticoagulant activities of Dicoumarol.
TestosteroneTestosterone may increase the anticoagulant activities of Dicoumarol.
TetracyclineTetracycline may increase the anticoagulant activities of Dicoumarol.
Thyroid extractThyroid extract may increase the anticoagulant activities of Dicoumarol.
Tiaprofenic acidTiaprofenic acid 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.
TinzaparinDicoumarol may increase the anticoagulant activities of Tinzaparin.
TipranavirTipranavir may increase the anticoagulant activities of Dicoumarol.
TirofibanTirofiban may increase the anticoagulant activities of Dicoumarol.
TolazamideTolazamide 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.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Dicoumarol.
TrimethoprimTrimethoprim may increase the anticoagulant activities of Dicoumarol.
TrimipramineTrimipramine may increase the anticoagulant activities of Dicoumarol.
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.
ZafirlukastThe serum concentration of Dicoumarol can be increased when it is combined with Zafirlukast.
Food InteractionsNot Available

Targets

1. Vitamin K epoxide reductase complex subunit 1

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Vitamin K epoxide reductase complex subunit 1 Q9BQB6 Details

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
  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
  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
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. NAD(P)H dehydrogenase [quinone] 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
NAD(P)H dehydrogenase [quinone] 1 P15559 Details

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
  2. Jaiswal AK: Characterization and partial purification of microsomal NADH:quinone oxidoreductases. Arch Biochem Biophys. 2000 Mar 1;375(1):62-8. Pubmed
  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
  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
  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
  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

3. Quinone oxidoreductase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Quinone oxidoreductase Q08257 Details

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
  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
  3. Asher G, Dym O, Tsvetkov P, Adler J, Shaul Y: The crystal structure of NADH quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol. Biochemistry. 2006 May 23;45(20):6372-8. Pubmed
  4. Maser E, Gebel T, Netter KJ: Carbonyl reduction of metyrapone in human liver. Biochem Pharmacol. 1991 Dec 11;42 Suppl:S93-8. Pubmed
  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

Enzymes

1. Cytochrome P450 2C9

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 25, 2013 16:59