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Identification
NamePhenprocoumon
Accession NumberDB00946  (APRD00228)
TypeSmall Molecule
GroupsApproved
DescriptionCoumarin derivative that acts as a long acting oral anticoagulant. [PubChem]
Structure
Thumb
Synonyms
3-(1-Phenylpropyl)-4-hydroxycoumarin
3-(1'-Phenyl-propyl)-4-oxycoumarin
3-(alpha-Ethylbenzyl)-4-hydroxycoumarin
3-(alpha-Phenylpropyl)-4-hydroxycoumarin
4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one
4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
Fenprocumon
Fenprocumone
Phenprocoumarol
Phenprocoumarole
Phenprocoumone
Phenprocoumonum
Phenprocumone
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
FalithromNot Available
MarcoumarNot Available
MarcumarNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIQ08SIO485D
CAS number435-97-2
WeightAverage: 280.3178
Monoisotopic: 280.109944378
Chemical FormulaC18H16O3
InChI KeyInChIKey=DQDAYGNAKTZFIW-UHFFFAOYSA-N
InChI
InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
IUPAC Name
4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
SMILES
CCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=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
  • Phenylpropane
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed for the prevention and treatment of thromboembolic disease including venous thrombosis, thromboembolism, and pulmonary embolism as well as for the prevention of ischemic stroke in patients with atrial fibrillation (AF).
PharmacodynamicsPhenprocoumon, a coumarin anticoagulant, thins the blood by antagonizing vitamin K which is required for the production of clotting factors in the liver. Anticoagulants such as phenprocoumon have no direct effect on an established thrombus, nor do they reverse ischemic tissue damage (damage caused by an inadequate blood supply to an organ or part of the body). However, once a thrombus has occurred, the goal of anticoagulant treatment is to prevent further extension of the formed clot and prevent secondary thromboembolic complications which may result in serious and possibly fatal sequelae.
Mechanism of actionPhenprocoumon 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 decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
Related Articles
AbsorptionBioavailability is close to 100%
Volume of distributionNot Available
Protein binding99%
Metabolism

Phenprocoumon is stereoselectively metabolized by hepatic microsomal enzymes (cytochrome P-450) to inactive hydroxylated metabolites (predominant route) and by reductases to reduced metabolites. Cytochrome P450 2C9 is the principal form of human liver P-450 responsible for metabolism.

SubstrateEnzymesProduct
Phenprocoumon
4'-Hydroxy-R-phenprocoumonDetails
Phenprocoumon
6-Hydroxy-R-phenprocoumonDetails
Phenprocoumon
8-Hydroxy-R-phenprocoumonDetails
Phenprocoumon
7-Hydroxy-R-phenprocoumonDetails
Route of eliminationNot Available
Half life5-6 days
ClearanceNot Available
Toxicity50=500 mg/kg. Symptoms of overdose includes suspected or overt abnormal bleeding (e.g., appearance of blood in stools or urine, hematuria, excessive menstrual bleeding, melena, petechiae, excessive bruising or persistent oozing from superficial injuries).
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Phenprocoumon Action PathwayDrug actionSMP00271
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.992
Blood Brain Barrier+0.8992
Caco-2 permeable+0.8924
P-glycoprotein substrateSubstrate0.5545
P-glycoprotein inhibitor INon-inhibitor0.8579
P-glycoprotein inhibitor IINon-inhibitor0.8896
Renal organic cation transporterNon-inhibitor0.8798
CYP450 2C9 substrateNon-substrate0.6832
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.687
CYP450 1A2 substrateInhibitor0.6462
CYP450 2C9 inhibitorInhibitor0.7572
CYP450 2D6 inhibitorNon-inhibitor0.9555
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorNon-inhibitor0.9032
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6013
Ames testNon AMES toxic0.8363
CarcinogenicityNon-carcinogens0.9044
BiodegradationNot ready biodegradable0.8477
Rat acute toxicity3.1784 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9105
hERG inhibition (predictor II)Non-inhibitor0.9479
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Organon usa inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point179.5 °CPhysProp
water solubility12.9 mg/LNot Available
logP3.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0486 mg/mLALOGPS
logP3.81ALOGPS
logP3.74ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.64 m3·mol-1ChemAxon
Polarizability29.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (10.9 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 ReferencesNot Available
External Links
ATC CodesB01AA04
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabAbciximab may increase the anticoagulant activities of Phenprocoumon.
AbirateroneThe serum concentration of Phenprocoumon can be increased when it is combined with Abiraterone.
AceclofenacAceclofenac may increase the anticoagulant activities of Phenprocoumon.
AcenocoumarolPhenprocoumon may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenAcetaminophen may increase the anticoagulant activities of Phenprocoumon.
AcetohexamideAcetohexamide may increase the anticoagulant activities of Phenprocoumon.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Phenprocoumon.
AdapaleneAdapalene may increase the anticoagulant activities of Phenprocoumon.
AllopurinolAllopurinol may increase the anticoagulant activities of Phenprocoumon.
AllylestrenolThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Allylestrenol.
AlprostadilAlprostadil may increase the anticoagulant activities of Phenprocoumon.
AlteplaseAlteplase may increase the anticoagulant activities of Phenprocoumon.
AltrenogestThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Altrenogest.
ALX-0081ALX-0081 may increase the anticoagulant activities of Phenprocoumon.
AmdinocillinAmdinocillin may increase the anticoagulant activities of Phenprocoumon.
AmineptineAmineptine may increase the anticoagulant activities of Phenprocoumon.
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Phenprocoumon.
AmiodaroneThe metabolism of Phenprocoumon can be decreased when combined with Amiodarone.
AmitriptylineAmitriptyline may increase the anticoagulant activities of Phenprocoumon.
AmobarbitalThe metabolism of Phenprocoumon can be increased when combined with Amobarbital.
AmoxapineAmoxapine may increase the anticoagulant activities of Phenprocoumon.
AmoxicillinAmoxicillin may increase the anticoagulant activities of Phenprocoumon.
AmpicillinAmpicillin may increase the anticoagulant activities of Phenprocoumon.
AnagrelideAnagrelide may increase the anticoagulant activities of Phenprocoumon.
AncrodPhenprocoumon may increase the anticoagulant activities of Ancrod.
AnistreplaseAnistreplase may increase the anticoagulant activities of Phenprocoumon.
AntipyrineAntipyrine may increase the anticoagulant activities of Phenprocoumon.
Antithrombin III humanPhenprocoumon may increase the anticoagulant activities of Antithrombin III human.
ApixabanApixaban may increase the anticoagulant activities of Phenprocoumon.
ApremilastApremilast may increase the anticoagulant activities of Phenprocoumon.
AprepitantThe serum concentration of Phenprocoumon can be increased when it is combined with Aprepitant.
AprotininThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Aprotinin.
ArdeparinArdeparin may increase the anticoagulant activities of Phenprocoumon.
ArgatrobanArgatroban may increase the anticoagulant activities of Phenprocoumon.
AstaxanthinAstaxanthin may increase the anticoagulant activities of Phenprocoumon.
AtazanavirThe metabolism of Phenprocoumon can be decreased when combined with Atazanavir.
AtomoxetineThe metabolism of Phenprocoumon can be decreased when combined with Atomoxetine.
AtorvastatinAtorvastatin may increase the anticoagulant activities of Phenprocoumon.
AzapropazoneAzapropazone may increase the anticoagulant activities of Phenprocoumon.
AzathioprineAzathioprine may decrease the anticoagulant activities of Phenprocoumon.
AzelastineAzelastine may increase the anticoagulant activities of Phenprocoumon.
AzlocillinAzlocillin may increase the anticoagulant activities of Phenprocoumon.
BalsalazideBalsalazide may increase the anticoagulant activities of Phenprocoumon.
BarbitalThe metabolism of Phenprocoumon can be increased when combined with Barbital.
BatroxobinBatroxobin may increase the anticoagulant activities of Phenprocoumon.
BazedoxifeneBazedoxifene may decrease the anticoagulant activities of Phenprocoumon.
BecaplerminBecaplermin may increase the anticoagulant activities of Phenprocoumon.
BemiparinBemiparin may increase the anticoagulant activities of Phenprocoumon.
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Phenprocoumon.
Benzathine benzylpenicillinBenzathine benzylpenicillin may increase the anticoagulant activities of Phenprocoumon.
BenzylpenicillinBenzylpenicillin may increase the anticoagulant activities of Phenprocoumon.
Benzylpenicillin PotassiumBenzylpenicillin Potassium may increase the anticoagulant activities of Phenprocoumon.
BeraprostBeraprost may increase the anticoagulant activities of Phenprocoumon.
BexaroteneThe serum concentration of Phenprocoumon can be decreased when it is combined with Bexarotene.
BezafibrateBezafibrate may increase the anticoagulant activities of Phenprocoumon.
BicalutamideThe serum concentration of Phenprocoumon can be increased when it is combined with Bicalutamide.
BivalirudinBivalirudin may increase the anticoagulant activities of Phenprocoumon.
BoceprevirThe metabolism of Phenprocoumon can be decreased when combined with Boceprevir.
BortezomibThe metabolism of Phenprocoumon can be decreased when combined with Bortezomib.
BosentanThe serum concentration of Phenprocoumon can be decreased when it is combined with Bosentan.
BromfenacBromfenac may increase the anticoagulant activities of Phenprocoumon.
CangrelorCangrelor may increase the anticoagulant activities of Phenprocoumon.
CapecitabineThe serum concentration of Phenprocoumon can be increased when it is combined with Capecitabine.
CarbamazepineThe serum concentration of Phenprocoumon can be decreased when it is combined with Carbamazepine.
CarbenicillinCarbenicillin may increase the anticoagulant activities of Phenprocoumon.
CarbimazoleCarbimazole may decrease the anticoagulant activities of Phenprocoumon.
CarprofenCarprofen may increase the anticoagulant activities of Phenprocoumon.
CastanospermineCastanospermine may increase the anticoagulant activities of Phenprocoumon.
CefacetrileCefacetrile may increase the anticoagulant activities of Phenprocoumon.
CefaclorCefaclor may increase the anticoagulant activities of Phenprocoumon.
CefadroxilCefadroxil may increase the anticoagulant activities of Phenprocoumon.
CefalotinCefalotin may increase the anticoagulant activities of Phenprocoumon.
CefamandoleCefamandole may increase the anticoagulant activities of Phenprocoumon.
CefapirinCefapirin may increase the anticoagulant activities of Phenprocoumon.
CefazolinCefazolin may increase the anticoagulant activities of Phenprocoumon.
CefiximeCefixime may increase the anticoagulant activities of Phenprocoumon.
CefmenoximeCefmenoxime may increase the anticoagulant activities of Phenprocoumon.
CefmetazoleCefmetazole may increase the anticoagulant activities of Phenprocoumon.
CefonicidCefonicid may increase the anticoagulant activities of Phenprocoumon.
CefoperazoneCefoperazone may increase the anticoagulant activities of Phenprocoumon.
CefotaximeCefotaxime may increase the anticoagulant activities of Phenprocoumon.
CefotetanCefotetan may increase the anticoagulant activities of Phenprocoumon.
CefotiamCefotiam may increase the anticoagulant activities of Phenprocoumon.
CefoxitinCefoxitin may increase the anticoagulant activities of Phenprocoumon.
CefradineCefradine may increase the anticoagulant activities of Phenprocoumon.
CeftazidimeCeftazidime may increase the anticoagulant activities of Phenprocoumon.
CeftizoximeCeftizoxime may increase the anticoagulant activities of Phenprocoumon.
CeftriaxoneCeftriaxone may increase the anticoagulant activities of Phenprocoumon.
CefuroximeCefuroxime may increase the anticoagulant activities of Phenprocoumon.
CelecoxibCelecoxib may increase the anticoagulant activities of Phenprocoumon.
CephalexinCephalexin may increase the anticoagulant activities of Phenprocoumon.
CephaloglycinCephaloglycin may increase the anticoagulant activities of Phenprocoumon.
CephaloridineCephaloridine may increase the anticoagulant activities of Phenprocoumon.
CeritinibThe serum concentration of Phenprocoumon can be increased when it is combined with Ceritinib.
CerivastatinCerivastatin may increase the anticoagulant activities of Phenprocoumon.
CertoparinPhenprocoumon may increase the anticoagulant activities of Certoparin.
Chloral hydrateThe serum concentration of Phenprocoumon can be increased when it is combined with Chloral hydrate.
ChloramphenicolChloramphenicol may increase the anticoagulant activities of Phenprocoumon.
ChloroquineChloroquine may increase the anticoagulant activities of Phenprocoumon.
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Phenprocoumon.
ChlorpropamideChlorpropamide may increase the anticoagulant activities of Phenprocoumon.
CholecalciferolThe metabolism of Phenprocoumon can be decreased when combined with Cholecalciferol.
CholestyramineCholestyramine can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.
CilostazolCilostazol may increase the anticoagulant activities of Phenprocoumon.
CimetidineCimetidine may increase the anticoagulant activities of Phenprocoumon.
CiprofibrateCiprofibrate may increase the anticoagulant activities of Phenprocoumon.
CitalopramCitalopram may increase the anticoagulant activities of Phenprocoumon.
Citric AcidPhenprocoumon may increase the anticoagulant activities of Citric Acid.
ClarithromycinThe metabolism of Phenprocoumon can be decreased when combined with Clarithromycin.
ClemastineThe metabolism of Phenprocoumon can be decreased when combined with Clemastine.
ClofibrateClofibrate may increase the anticoagulant activities of Phenprocoumon.
ClomipramineClomipramine may increase the anticoagulant activities of Phenprocoumon.
ClonixinClonixin may increase the anticoagulant activities of Phenprocoumon.
ClopidogrelClopidogrel may increase the anticoagulant activities of Phenprocoumon.
ClotrimazoleThe metabolism of Phenprocoumon can be decreased when combined with Clotrimazole.
CloxacillinCloxacillin may decrease the anticoagulant activities of Phenprocoumon.
CobicistatThe metabolism of Phenprocoumon can be decreased when combined with Cobicistat.
Coenzyme Q10Coenzyme Q10 may increase the anticoagulant activities of Phenprocoumon.
ColesevelamColesevelam can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Collagenase.
ConivaptanThe serum concentration of Phenprocoumon can be increased when it is combined with Conivaptan.
Conjugated Equine EstrogensConjugated Equine Estrogens may decrease the anticoagulant activities of Phenprocoumon.
CranberryCranberry may increase the anticoagulant activities of Phenprocoumon.
CrizotinibThe metabolism of Phenprocoumon can be decreased when combined with Crizotinib.
CyclacillinCyclacillin may increase the anticoagulant activities of Phenprocoumon.
CyclobenzaprineCyclobenzaprine may increase the anticoagulant activities of Phenprocoumon.
CyclosporineThe metabolism of Phenprocoumon can be decreased when combined with Cyclosporine.
D-LimoneneD-Limonene may increase the anticoagulant activities of Phenprocoumon.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Phenprocoumon.
DabrafenibThe serum concentration of Phenprocoumon can be decreased when it is combined with Dabrafenib.
DalteparinPhenprocoumon may increase the anticoagulant activities of Dalteparin.
DanaparoidPhenprocoumon may increase the anticoagulant activities of Danaparoid.
DapoxetineDapoxetine may increase the anticoagulant activities of Phenprocoumon.
DarunavirThe metabolism of Phenprocoumon can be decreased when combined with Darunavir.
DasatinibDasatinib may increase the anticoagulant activities of Phenprocoumon.
DeferasiroxThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Deferasirox.
DeferasiroxThe serum concentration of Phenprocoumon can be decreased when it is combined with Deferasirox.
DefibrotideDefibrotide may increase the anticoagulant activities of Phenprocoumon.
DelavirdineThe metabolism of Phenprocoumon can be decreased when combined with Delavirdine.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Deoxycholic Acid.
DesipramineDesipramine may increase the anticoagulant activities of Phenprocoumon.
DesirudinPhenprocoumon may increase the anticoagulant activities of Desirudin.
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Phenprocoumon.
DesogestrelThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Desogestrel.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Phenprocoumon.
DexamethasoneThe serum concentration of Phenprocoumon can be decreased when it is combined with Dexamethasone.
DexmethylphenidateThe serum concentration of Phenprocoumon can be increased when it is combined with Dexmethylphenidate.
DextranPhenprocoumon may increase the anticoagulant activities of Dextran.
Dextran 40Phenprocoumon may increase the anticoagulant activities of Dextran 40.
Dextran 70Phenprocoumon may increase the anticoagulant activities of Dextran 70.
Dextran 75Phenprocoumon may increase the anticoagulant activities of Dextran 75.
DiclofenacDiclofenac may increase the anticoagulant activities of Phenprocoumon.
DicloxacillinDicloxacillin may decrease the anticoagulant activities of Phenprocoumon.
DicoumarolDicoumarol may increase the anticoagulant activities of Phenprocoumon.
DienestrolDienestrol may decrease the anticoagulant activities of Phenprocoumon.
DienogestThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Dienogest.
DiethylstilbestrolDiethylstilbestrol may decrease the anticoagulant activities of Phenprocoumon.
DiflunisalDiflunisal may increase the anticoagulant activities of Phenprocoumon.
DihydroergotamineThe metabolism of Phenprocoumon can be decreased when combined with Dihydroergotamine.
DihydrotestosteroneDihydrotestosterone may increase the anticoagulant activities of Phenprocoumon.
DiltiazemThe metabolism of Phenprocoumon can be decreased when combined with Diltiazem.
DipyridamoleDipyridamole may increase the anticoagulant activities of Phenprocoumon.
DisulfiramThe serum concentration of Phenprocoumon can be increased when it is combined with Disulfiram.
DitazoleDitazole may increase the anticoagulant activities of Phenprocoumon.
DosulepinDosulepin may increase the anticoagulant activities of Phenprocoumon.
DoxepinDoxepin may increase the anticoagulant activities of Phenprocoumon.
DoxycyclineThe metabolism of Phenprocoumon can be decreased when combined with Doxycycline.
DronedaroneThe serum concentration of Phenprocoumon can be increased when it is combined with Dronedarone.
DrospirenoneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Drospirenone.
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Phenprocoumon.
DroxicamDroxicam may increase the anticoagulant activities of Phenprocoumon.
DydrogesteroneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Dydrogesterone.
EconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Econazole.
Edetic AcidPhenprocoumon may increase the anticoagulant activities of Edetic Acid.
EdoxabanEdoxaban may increase the anticoagulant activities of Phenprocoumon.
EfavirenzThe serum concentration of Phenprocoumon can be decreased when it is combined with Efavirenz.
EnoxaparinPhenprocoumon may increase the anticoagulant activities of Enoxaparin.
EnzalutamideThe serum concentration of Phenprocoumon can be decreased when it is combined with Enzalutamide.
EpinastineEpinastine may increase the anticoagulant activities of Phenprocoumon.
EpirizoleEpirizole may increase the anticoagulant activities of Phenprocoumon.
EpoprostenolEpoprostenol may increase the anticoagulant activities of Phenprocoumon.
EpoprostenolThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Epoprostenol.
EptifibatideEptifibatide may increase the anticoagulant activities of Phenprocoumon.
ErythromycinThe serum concentration of Phenprocoumon can be increased when it is combined with Erythromycin.
EscitalopramEscitalopram may increase the anticoagulant activities of Phenprocoumon.
Eslicarbazepine acetateThe serum concentration of Phenprocoumon can be decreased when it is combined with Eslicarbazepine acetate.
EsmirtazapineEsmirtazapine may increase the anticoagulant activities of Phenprocoumon.
EsomeprazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Esomeprazole.
EstradiolEstradiol may decrease the anticoagulant activities of Phenprocoumon.
EstriolEstriol may decrease the anticoagulant activities of Phenprocoumon.
EstroneEstrone may decrease the anticoagulant activities of Phenprocoumon.
Etacrynic acidThe serum concentration of Phenprocoumon can be increased when it is combined with Etacrynic acid.
EtanerceptEtanercept may increase the anticoagulant activities of Phenprocoumon.
EthanolThe serum concentration of Phenprocoumon can be decreased when it is combined with Ethanol.
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Phenprocoumon.
EthotoinEthotoin may increase the anticoagulant activities of Phenprocoumon.
Ethyl biscoumacetatePhenprocoumon may increase the anticoagulant activities of Ethyl biscoumacetate.
EtodolacEtodolac may increase the anticoagulant activities of Phenprocoumon.
EtofenamateEtofenamate may increase the anticoagulant activities of Phenprocoumon.
EtofibrateEtofibrate may increase the anticoagulant activities of Phenprocoumon.
EtonogestrelThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Etonogestrel.
EtoperidoneEtoperidone may increase the anticoagulant activities of Phenprocoumon.
EtoposideEtoposide may increase the anticoagulant activities of Phenprocoumon.
EtoricoxibEtoricoxib may increase the anticoagulant activities of Phenprocoumon.
EtravirineThe serum concentration of Phenprocoumon can be decreased when it is combined with Etravirine.
Evening primrose oilEvening primrose oil may increase the anticoagulant activities of Phenprocoumon.
ExenatideExenatide may increase the anticoagulant activities of Phenprocoumon.
exisulindexisulind may increase the anticoagulant activities of Phenprocoumon.
FelodipineThe metabolism of Phenprocoumon can be decreased when combined with Felodipine.
FenbufenFenbufen may increase the anticoagulant activities of Phenprocoumon.
FenfluramineFenfluramine may increase the anticoagulant activities of Phenprocoumon.
FenofibrateFenofibrate may increase the anticoagulant activities of Phenprocoumon.
FenoprofenFenoprofen may increase the anticoagulant activities of Phenprocoumon.
FibrinolysinFibrinolysin may increase the anticoagulant activities of Phenprocoumon.
FloctafenineFloctafenine may increase the anticoagulant activities of Phenprocoumon.
FloxuridineThe metabolism of Phenprocoumon can be decreased when combined with Floxuridine.
FlucloxacillinFlucloxacillin may increase the anticoagulant activities of Phenprocoumon.
FluconazoleThe metabolism of Phenprocoumon can be decreased when combined with Fluconazole.
FlunixinFlunixin may increase the anticoagulant activities of Phenprocoumon.
FluorouracilThe serum concentration of Phenprocoumon can be increased when it is combined with Fluorouracil.
FluoxetineFluoxetine may increase the anticoagulant activities of Phenprocoumon.
FluoxymesteroneFluoxymesterone may increase the anticoagulant activities of Phenprocoumon.
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Phenprocoumon.
FluvastatinFluvastatin may increase the anticoagulant activities of Phenprocoumon.
FluvoxamineFluvoxamine may increase the anticoagulant activities of Phenprocoumon.
Fondaparinux sodiumFondaparinux sodium may increase the anticoagulant activities of Phenprocoumon.
FosamprenavirThe metabolism of Phenprocoumon can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Phenprocoumon can be increased when it is combined with Fosaprepitant.
FosphenytoinFosphenytoin may increase the anticoagulant activities of Phenprocoumon.
Fusidic AcidThe serum concentration of Phenprocoumon can be increased when it is combined with Fusidic Acid.
GefitinibGefitinib may increase the anticoagulant activities of Phenprocoumon.
GemfibrozilGemfibrozil may increase the anticoagulant activities of Phenprocoumon.
GenisteinGenistein may decrease the anticoagulant activities of Phenprocoumon.
GestodeneThe therapeutic efficacy of Phenprocoumon 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 Phenprocoumon.
GlibornurideGlibornuride may increase the anticoagulant activities of Phenprocoumon.
GliclazideGliclazide may increase the anticoagulant activities of Phenprocoumon.
GlimepirideGlimepiride may increase the anticoagulant activities of Phenprocoumon.
GlipizideGlipizide may increase the anticoagulant activities of Phenprocoumon.
GliquidoneGliquidone may increase the anticoagulant activities of Phenprocoumon.
GlisoxepideGlisoxepide may increase the anticoagulant activities of Phenprocoumon.
Glucagon recombinantGlucagon recombinant may increase the anticoagulant activities of Phenprocoumon.
GlutethimideThe metabolism of Phenprocoumon can be increased when combined with Glutethimide.
GlyburideGlyburide may increase the anticoagulant activities of Phenprocoumon.
GriseofulvinThe serum concentration of Phenprocoumon can be decreased when it is combined with Griseofulvin.
HeminHemin may increase the anticoagulant activities of Phenprocoumon.
HeparinPhenprocoumon may increase the anticoagulant activities of Heparin.
HexestrolHexestrol may decrease the anticoagulant activities of Phenprocoumon.
HexobarbitalThe metabolism of Phenprocoumon can be increased when combined with Hexobarbital.
HirulogPhenprocoumon may increase the anticoagulant activities of Hirulog.
HMPL-004HMPL-004 may increase the anticoagulant activities of Phenprocoumon.
Hydroxyprogesterone caproateThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Hydroxyprogesterone caproate.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Ibritumomab tiuxetan.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Phenprocoumon.
IbudilastIbudilast may increase the anticoagulant activities of Phenprocoumon.
IbuprofenIbuprofen may increase the anticoagulant activities of Phenprocoumon.
IbuproxamIbuproxam may increase the anticoagulant activities of Phenprocoumon.
IcatibantIcatibant may increase the anticoagulant activities of Phenprocoumon.
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Phenprocoumon.
IdelalisibThe serum concentration of Phenprocoumon can be increased when it is combined with Idelalisib.
IfenprodilIfenprodil may increase the anticoagulant activities of Phenprocoumon.
IfosfamideIfosfamide may increase the anticoagulant activities of Phenprocoumon.
IloprostIloprost may increase the anticoagulant activities of Phenprocoumon.
IloprostThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Iloprost.
ImatinibThe metabolism of Phenprocoumon can be decreased when combined with Imatinib.
ImipramineImipramine may increase the anticoagulant activities of Phenprocoumon.
IndalpineIndalpine may increase the anticoagulant activities of Phenprocoumon.
IndinavirThe metabolism of Phenprocoumon can be decreased when combined with Indinavir.
IndomethacinIndomethacin may increase the anticoagulant activities of Phenprocoumon.
IndoprofenIndoprofen may increase the anticoagulant activities of Phenprocoumon.
IrbesartanThe metabolism of Phenprocoumon can be decreased when combined with Irbesartan.
IsavuconazoniumThe metabolism of Phenprocoumon can be decreased when combined with Isavuconazonium.
IsoxicamIsoxicam may increase the anticoagulant activities of Phenprocoumon.
IsradipineThe metabolism of Phenprocoumon can be decreased when combined with Isradipine.
ItraconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Phenprocoumon can be increased when it is combined with Ivacaftor.
IvermectinIvermectin may increase the anticoagulant activities of Phenprocoumon.
KebuzoneKebuzone may increase the anticoagulant activities of Phenprocoumon.
KetoconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Ketoconazole.
KetoprofenKetoprofen may increase the anticoagulant activities of Phenprocoumon.
KetorolacKetorolac may increase the anticoagulant activities of Phenprocoumon.
L-CarnitineL-Carnitine may increase the anticoagulant activities of Phenprocoumon.
LansoprazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Lansoprazole.
LapatinibThe metabolism of Phenprocoumon can be decreased when combined with Lapatinib.
LeflunomideLeflunomide may increase the anticoagulant activities of Phenprocoumon.
LepirudinLepirudin may increase the anticoagulant activities of Phenprocoumon.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Phenprocoumon.
LevonorgestrelThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Levonorgestrel.
LevothyroxineLevothyroxine may increase the anticoagulant activities of Phenprocoumon.
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Phenprocoumon.
LiothyronineLiothyronine may increase the anticoagulant activities of Phenprocoumon.
LiotrixLiotrix may increase the anticoagulant activities of Phenprocoumon.
LixisenatideLixisenatide can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.
LopinavirThe metabolism of Phenprocoumon can be decreased when combined with Lopinavir.
LornoxicamLornoxicam may increase the anticoagulant activities of Phenprocoumon.
LosartanThe metabolism of Phenprocoumon can be decreased when combined with Losartan.
LovastatinLovastatin may increase the anticoagulant activities of Phenprocoumon.
LoxoprofenLoxoprofen may increase the anticoagulant activities of Phenprocoumon.
Lu AA21004Lu AA21004 may increase the anticoagulant activities of Phenprocoumon.
LuliconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Luliconazole.
LumacaftorThe serum concentration of Phenprocoumon can be decreased when it is combined with Lumacaftor.
LumiracoxibLumiracoxib may increase the anticoagulant activities of Phenprocoumon.
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Phenprocoumon.
MasoprocolMasoprocol may increase the anticoagulant activities of Phenprocoumon.
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Phenprocoumon.
MedrogestoneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Medrogestone.
Medroxyprogesterone acetateThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Medroxyprogesterone acetate.
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Phenprocoumon.
Megestrol acetateThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Megestrol acetate.
MeloxicamMeloxicam may increase the anticoagulant activities of Phenprocoumon.
MercaptopurineMercaptopurine may decrease the anticoagulant activities of Phenprocoumon.
MesalazineMesalazine may increase the anticoagulant activities of Phenprocoumon.
MestranolMestranol may decrease the anticoagulant activities of Phenprocoumon.
MetamizoleMetamizole may increase the anticoagulant activities of Phenprocoumon.
MethimazoleMethimazole may decrease the anticoagulant activities of Phenprocoumon.
MethohexitalThe metabolism of Phenprocoumon can be increased when combined with Methohexital.
MethylphenidateThe serum concentration of Phenprocoumon can be increased when it is combined with Methylphenidate.
MethylphenobarbitalThe metabolism of Phenprocoumon can be increased when combined with Methylphenobarbital.
MethyltestosteroneMethyltestosterone may increase the anticoagulant activities of Phenprocoumon.
MeticillinMeticillin may increase the anticoagulant activities of Phenprocoumon.
MetronidazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Metronidazole.
MevastatinMevastatin may increase the anticoagulant activities of Phenprocoumon.
MezlocillinMezlocillin may increase the anticoagulant activities of Phenprocoumon.
MiconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Miconazole.
MifepristoneThe metabolism of Phenprocoumon can be decreased when combined with Mifepristone.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Phenprocoumon.
MilrinoneMilrinone may increase the anticoagulant activities of Phenprocoumon.
MirtazapineMirtazapine may increase the anticoagulant activities of Phenprocoumon.
MitotaneThe serum concentration of Phenprocoumon can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Phenprocoumon can be decreased when it is combined with Modafinil.
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Phenprocoumon.
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Phenprocoumon.
NabumetoneNabumetone may increase the anticoagulant activities of Phenprocoumon.
NadroparinPhenprocoumon may increase the anticoagulant activities of Nadroparin.
NafcillinNafcillin may increase the anticoagulant activities of Phenprocoumon.
NaftifineNaftifine may increase the anticoagulant activities of Phenprocoumon.
NaproxenNaproxen may increase the anticoagulant activities of Phenprocoumon.
NCX 4016NCX 4016 may increase the anticoagulant activities of Phenprocoumon.
NefazodoneThe metabolism of Phenprocoumon can be decreased when combined with Nefazodone.
NelfinavirThe metabolism of Phenprocoumon can be decreased when combined with Nelfinavir.
NeomycinNeomycin may increase the anticoagulant activities of Phenprocoumon.
NepafenacNepafenac may increase the anticoagulant activities of Phenprocoumon.
NetupitantThe serum concentration of Phenprocoumon can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Phenprocoumon can be decreased when combined with Nevirapine.
NicardipineThe metabolism of Phenprocoumon can be decreased when combined with Nicardipine.
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Phenprocoumon.
NilotinibThe metabolism of Phenprocoumon can be decreased when combined with Nilotinib.
NimesulideNimesulide may increase the anticoagulant activities of Phenprocoumon.
NintedanibThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Nintedanib.
NorethisteroneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Norethisterone.
NortriptylineNortriptyline may increase the anticoagulant activities of Phenprocoumon.
ObinutuzumabThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Obinutuzumab.
OlanzapineOlanzapine may increase the anticoagulant activities of Phenprocoumon.
OlaparibThe metabolism of Phenprocoumon can be decreased when combined with Olaparib.
OlopatadineOlopatadine may increase the anticoagulant activities of Phenprocoumon.
OlsalazineOlsalazine may increase the anticoagulant activities of Phenprocoumon.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Omacetaxine mepesuccinate.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Phenprocoumon.
OmeprazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Omeprazole.
OrgoteinOrgotein may increase the anticoagulant activities of Phenprocoumon.
OritavancinThe serum concentration of Phenprocoumon can be increased when it is combined with Oritavancin.
OsimertinibThe serum concentration of Phenprocoumon can be increased when it is combined with Osimertinib.
OtamixabanPhenprocoumon may increase the anticoagulant activities of Otamixaban.
OxacillinOxacillin may increase the anticoagulant activities of Phenprocoumon.
OxandroloneOxandrolone may increase the anticoagulant activities of Phenprocoumon.
OxaprozinOxaprozin may increase the anticoagulant activities of Phenprocoumon.
OxymetholoneOxymetholone may increase the anticoagulant activities of Phenprocoumon.
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Phenprocoumon.
PalbociclibThe serum concentration of Phenprocoumon can be increased when it is combined with Palbociclib.
ParecoxibParecoxib may increase the anticoagulant activities of Phenprocoumon.
ParnaparinParnaparin may increase the anticoagulant activities of Phenprocoumon.
ParoxetineParoxetine may increase the anticoagulant activities of Phenprocoumon.
PentobarbitalThe metabolism of Phenprocoumon can be increased when combined with Pentobarbital.
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Phenprocoumon.
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Phenprocoumon.
PhenindionePhenindione may increase the anticoagulant activities of Phenprocoumon.
PhenobarbitalThe metabolism of Phenprocoumon can be increased when combined with Phenobarbital.
PhenoxymethylpenicillinPhenoxymethylpenicillin may increase the anticoagulant activities of Phenprocoumon.
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Phenprocoumon.
PhenytoinPhenytoin may increase the anticoagulant activities of Phenprocoumon.
PhylloquinonePhylloquinone may decrease the anticoagulant activities of Phenprocoumon.
PimecrolimusPimecrolimus may increase the anticoagulant activities of Phenprocoumon.
PioglitazoneThe metabolism of Phenprocoumon can be decreased when combined with Pioglitazone.
PiperacillinPiperacillin may increase the anticoagulant activities of Phenprocoumon.
PirfenidonePirfenidone may increase the anticoagulant activities of Phenprocoumon.
PiroxicamPiroxicam may increase the anticoagulant activities of Phenprocoumon.
PitavastatinPitavastatin may increase the anticoagulant activities of Phenprocoumon.
PivampicillinPivampicillin may increase the anticoagulant activities of Phenprocoumon.
PivmecillinamPivmecillinam may increase the anticoagulant activities of Phenprocoumon.
PlasminPlasmin may increase the anticoagulant activities of Phenprocoumon.
Polyestradiol phosphatePolyestradiol phosphate may decrease the anticoagulant activities of Phenprocoumon.
PosaconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Posaconazole.
PrasugrelPrasugrel may increase the anticoagulant activities of Phenprocoumon.
PravastatinPravastatin may increase the anticoagulant activities of Phenprocoumon.
PrimidoneThe metabolism of Phenprocoumon can be increased when combined with Primidone.
Procaine benzylpenicillinProcaine benzylpenicillin may increase the anticoagulant activities of Phenprocoumon.
ProgesteroneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Progesterone.
PropacetamolPropacetamol may increase the anticoagulant activities of Phenprocoumon.
PropafenoneThe serum concentration of Phenprocoumon can be increased when it is combined with Propafenone.
PropylthiouracilPropylthiouracil may decrease the anticoagulant activities of Phenprocoumon.
Protein CPhenprocoumon may increase the anticoagulant activities of Protein C.
ProtocatechualdehydePhenprocoumon may increase the anticoagulant activities of Protocatechualdehyde.
ProtriptylineProtriptyline may increase the anticoagulant activities of Phenprocoumon.
PTC299PTC299 may increase the anticoagulant activities of Phenprocoumon.
PyrimethamineThe metabolism of Phenprocoumon can be decreased when combined with Pyrimethamine.
QuinestrolQuinestrol may decrease the anticoagulant activities of Phenprocoumon.
QuinidineQuinidine may increase the anticoagulant activities of Phenprocoumon.
QuinineQuinine may increase the anticoagulant activities of Phenprocoumon.
RabeprazoleThe metabolism of Phenprocoumon can be decreased when combined with Rabeprazole.
RanolazineThe metabolism of Phenprocoumon can be decreased when combined with Ranolazine.
ResveratrolResveratrol may increase the anticoagulant activities of Phenprocoumon.
ReteplaseReteplase may increase the anticoagulant activities of Phenprocoumon.
ReviparinPhenprocoumon may increase the anticoagulant activities of Reviparin.
RidogrelRidogrel may increase the anticoagulant activities of Phenprocoumon.
RifabutinThe metabolism of Phenprocoumon can be increased when combined with Rifabutin.
RifampicinThe metabolism of Phenprocoumon can be increased when combined with Rifampicin.
RifapentineThe metabolism of Phenprocoumon can be increased when combined with Rifapentine.
RitonavirThe metabolism of Phenprocoumon can be decreased when combined with Ritonavir.
RivaroxabanPhenprocoumon may increase the anticoagulant activities of Rivaroxaban.
RofecoxibRofecoxib may increase the anticoagulant activities of Phenprocoumon.
RosiglitazoneRosiglitazone may increase the anticoagulant activities of Phenprocoumon.
RosuvastatinRosuvastatin may increase the anticoagulant activities of Phenprocoumon.
SalicylamideSalicylamide may increase the anticoagulant activities of Phenprocoumon.
Salicylic acidSalicylic acid may increase the anticoagulant activities of Phenprocoumon.
SalsalateSalsalate may increase the anticoagulant activities of Phenprocoumon.
SaquinavirThe metabolism of Phenprocoumon can be decreased when combined with Saquinavir.
SCH-530348SCH-530348 may increase the anticoagulant activities of Phenprocoumon.
SecobarbitalThe metabolism of Phenprocoumon can be increased when combined with Secobarbital.
SelexipagSelexipag may increase the anticoagulant activities of Phenprocoumon.
SeratrodastSeratrodast may increase the anticoagulant activities of Phenprocoumon.
SertralineSertraline may increase the anticoagulant activities of Phenprocoumon.
SevofluraneSevoflurane may increase the anticoagulant activities of Phenprocoumon.
SildenafilThe metabolism of Phenprocoumon can be decreased when combined with Sildenafil.
SiltuximabThe serum concentration of Phenprocoumon can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Phenprocoumon can be increased when it is combined with Simeprevir.
SimvastatinSimvastatin may increase the anticoagulant activities of Phenprocoumon.
SorafenibThe metabolism of Phenprocoumon can be decreased when combined with Sorafenib.
SRT501SRT501 may increase the anticoagulant activities of Phenprocoumon.
St. John's WortThe serum concentration of Phenprocoumon can be decreased when it is combined with St. John's Wort.
StanozololStanozolol may increase the anticoagulant activities of Phenprocoumon.
StiripentolThe serum concentration of Phenprocoumon can be increased when it is combined with Stiripentol.
StreptokinaseStreptokinase may increase the anticoagulant activities of Phenprocoumon.
SucralfateSucralfate may decrease the anticoagulant activities of Phenprocoumon.
SugammadexSugammadex may increase the anticoagulant activities of Phenprocoumon.
SulbactamSulbactam may increase the anticoagulant activities of Phenprocoumon.
SulfadiazineSulfadiazine may increase the anticoagulant activities of Phenprocoumon.
SulfamethoxazoleThe metabolism of Phenprocoumon can be decreased when combined with Sulfamethoxazole.
SulfasalazineSulfasalazine may increase the anticoagulant activities of Phenprocoumon.
SulfinpyrazoneThe metabolism of Phenprocoumon can be decreased when combined with Sulfinpyrazone.
SulfisoxazoleThe metabolism of Phenprocoumon can be decreased when combined with Sulfisoxazole.
SulindacSulindac may increase the anticoagulant activities of Phenprocoumon.
SulodexidePhenprocoumon may increase the anticoagulant activities of Sulodexide.
SuprofenSuprofen may increase the anticoagulant activities of Phenprocoumon.
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Phenprocoumon.
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Phenprocoumon.
TamoxifenThe serum concentration of Phenprocoumon can be increased when it is combined with Tamoxifen.
TegafurThe serum concentration of Phenprocoumon can be increased when it is combined with Tegafur.
TelaprevirThe metabolism of Phenprocoumon can be decreased when combined with Telaprevir.
TelithromycinThe metabolism of Phenprocoumon can be decreased when combined with Telithromycin.
TenecteplaseTenecteplase may increase the anticoagulant activities of Phenprocoumon.
TenoxicamTenoxicam may increase the anticoagulant activities of Phenprocoumon.
TepoxalinTepoxalin may increase the anticoagulant activities of Phenprocoumon.
TeriflunomideTeriflunomide may increase the anticoagulant activities of Phenprocoumon.
TesmilifeneTesmilifene may increase the anticoagulant activities of Phenprocoumon.
TestosteroneTestosterone may increase the anticoagulant activities of Phenprocoumon.
ThiamylalThe metabolism of Phenprocoumon can be increased when combined with Thiamylal.
ThiopentalThe metabolism of Phenprocoumon can be increased when combined with Thiopental.
Thyroid, porcineThyroid, porcine may increase the anticoagulant activities of Phenprocoumon.
TianeptineTianeptine may increase the anticoagulant activities of Phenprocoumon.
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Phenprocoumon.
TiboloneTibolone may increase the anticoagulant activities of Phenprocoumon.
TicagrelorTicagrelor may increase the anticoagulant activities of Phenprocoumon.
TicarcillinTicarcillin may increase the anticoagulant activities of Phenprocoumon.
TiclopidineTiclopidine may increase the anticoagulant activities of Phenprocoumon.
TinzaparinTinzaparin may increase the anticoagulant activities of Phenprocoumon.
TipranavirTipranavir may increase the anticoagulant activities of Phenprocoumon.
TirofibanTirofiban may increase the anticoagulant activities of Phenprocoumon.
TocilizumabThe serum concentration of Phenprocoumon can be decreased when it is combined with Tocilizumab.
TolazamideTolazamide may increase the anticoagulant activities of Phenprocoumon.
TolbutamideTolbutamide may increase the anticoagulant activities of Phenprocoumon.
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Phenprocoumon.
TolmetinTolmetin may increase the anticoagulant activities of Phenprocoumon.
ToremifeneToremifene may increase the anticoagulant activities of Phenprocoumon.
TositumomabThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Tositumomab.
TramadolTramadol may increase the anticoagulant activities of Phenprocoumon.
TranilastTranilast may increase the anticoagulant activities of Phenprocoumon.
TrapidilTrapidil may increase the anticoagulant activities of Phenprocoumon.
TrazodoneTrazodone may increase the anticoagulant activities of Phenprocoumon.
TreprostinilTreprostinil may increase the anticoagulant activities of Phenprocoumon.
TreprostinilThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Treprostinil.
TriflusalTriflusal may increase the anticoagulant activities of Phenprocoumon.
TrimethoprimThe metabolism of Phenprocoumon can be decreased when combined with Trimethoprim.
TrimipramineTrimipramine may increase the anticoagulant activities of Phenprocoumon.
Trisalicylate-cholineTrisalicylate-choline may increase the anticoagulant activities of Phenprocoumon.
UrokinaseUrokinase may increase the anticoagulant activities of Phenprocoumon.
ValdecoxibValdecoxib may increase the anticoagulant activities of Phenprocoumon.
Valproic AcidThe metabolism of Phenprocoumon can be decreased when combined with Valproic Acid.
ValsartanThe metabolism of Phenprocoumon can be decreased when combined with Valsartan.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Phenprocoumon.
VerapamilThe metabolism of Phenprocoumon can be decreased when combined with Verapamil.
VilazodoneVilazodone may increase the anticoagulant activities of Phenprocoumon.
Vitamin EVitamin E may increase the anticoagulant activities of Phenprocoumon.
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Phenprocoumon.
VoriconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Voriconazole.
VorinostatVorinostat may increase the anticoagulant activities of Phenprocoumon.
VortioxetineVortioxetine may increase the anticoagulant activities of Phenprocoumon.
WarfarinWarfarin may increase the anticoagulant activities of Phenprocoumon.
XimelagatranPhenprocoumon may increase the anticoagulant activities of Ximelagatran.
ZafirlukastThe serum concentration of Phenprocoumon can be increased when it is combined with Zafirlukast.
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Phenprocoumon.
ZeranolZeranol may decrease the anticoagulant activities of Phenprocoumon.
ZileutonZileuton may increase the anticoagulant activities of Phenprocoumon.
ZimelidineZimelidine may increase the anticoagulant activities of Phenprocoumon.
ZiprasidoneThe metabolism of Phenprocoumon can be decreased when combined with Ziprasidone.
ZomepiracZomepirac may increase the anticoagulant activities of Phenprocoumon.
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. Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [PubMed:17192772 ]
  2. Reitsma PH, van der Heijden JF, Groot AP, Rosendaal FR, Buller HR: A C1173T dimorphism in the VKORC1 gene determines coumarin sensitivity and bleeding risk. PLoS Med. 2005 Oct;2(10):e312. Epub 2005 Oct 11. [PubMed:16201835 ]
  3. Thijssen HH, Baars LG: Microsomal warfarin binding and vitamin K 2,3-epoxide reductase. Biochem Pharmacol. 1989 Apr 1;38(7):1115-20. [PubMed:2706010 ]
  4. Thijssen HH, Baars LG, Vervoort-Peters HT: Vitamin K 2,3-epoxide reductase: the basis for stereoselectivity of 4-hydroxycoumarin anticoagulant activity. Br J Pharmacol. 1988 Nov;95(3):675-82. [PubMed:3207986 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [PubMed:17192772 ]
  3. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Niedner R, von Oettingen U, Meyer F: [The reciprocal actions of phenprocoumon (Marcumar) with human serum albumin, erythrocytes and blood]. Int J Clin Pharmacol Biopharm. 1975 Dec;12(4):446-57. [PubMed:1205658 ]
  2. Fitos I, Visy J, Simonyi M: Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods. J Biochem Biophys Methods. 2002 Dec 31;54(1-3):71-84. [PubMed:12543492 ]
  3. Fitos I, Simonyi M: Stereoselective effect of phenprocoumon enantiomers on the binding of benzodiazepines to human serum albumin. Chirality. 1992;4(1):21-3. [PubMed:1642965 ]
  4. Rehse K, Fiedler B: [Determination of the protein binding of drugs by continuous ultrafiltration. 9. Comparison of the binding of nonsteroid antirheumatics to human serum albumin and their interaction with phenprocoumon]. Arch Pharm (Weinheim). 1989 Apr;322(4):241-3. [PubMed:2751413 ]
  5. Niedner R, von Oettingen U, Meyer F: [Binding of phenprocoumarol (Marcumar) to human albumin]. Int J Clin Pharmacol. 1973 Oct;8(2):160-6. [PubMed:4762907 ]
Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Not Available
Specific Function:
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction.
Gene Name:
ORM1
Uniprot ID:
P02763
Molecular Weight:
23511.38 Da
References
  1. Otagiri M, Maruyama T, Imai T, Imamura Y: Fluorescent investigations of binding of phenprocoumon to alpha 1-acid glycoprotein. J Pharm Sci. 1987 Aug;76(8):646-9. [PubMed:11002825 ]
  2. Hazai E, Visy J, Fitos I, Bikadi Z, Simonyi M: Selective binding of coumarin enantiomers to human alpha1-acid glycoprotein genetic variants. Bioorg Med Chem. 2006 Mar 15;14(6):1959-65. Epub 2005 Nov 15. [PubMed:16290938 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23