Identification
NamePhenprocoumon
Accession NumberDB00946  (APRD00228)
TypeSmall Molecule
GroupsApproved
Description

Coumarin 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 IDs Not Available
Product Ingredients 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
Categories
UNIIQ08SIO485D
CAS number435-97-2
WeightAverage: 280.3178
Monoisotopic: 280.109944378
Chemical FormulaC18H16O3
InChI KeyDQDAYGNAKTZFIW-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
Pharmacology
Indication

Used 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).

Structured Indications Not Available
Pharmacodynamics

Phenprocoumon, 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 action

Phenprocoumon 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Vitamin K epoxide reductase complex subunit 1Proteinyes
inhibitor
HumanQ9BQB6 details
Related Articles
Absorption

Bioavailability is close to 100%

Volume of distributionNot Available
Protein binding

99%

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 life

5-6 days

ClearanceNot Available
Toxicity

50=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
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*2(T;T) / (C;T)T Allele ADR Directly StudiedAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C Allele ADR Directly StudiedIf carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Vitamin K epoxide reductase complex subunit 1---(A;A) / (A;G)G > A ADR Directly StudiedIf carrier of CYP2C9*2 (rs1799853) or CYP2C9*3 (rs1057910) as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*6Not Available818delA ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*15Not Available485C>A ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAA ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*3Not Available1075A>C ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*4Not Available1076T>C ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*5Not Available1080C>G ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*8Not Available449G>A ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*11Not Available1003C>T ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*12Not Available1465C>T ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*13Not Available269T>C ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*14Not Available374G>A ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*16Not Available895A>G ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*26Not Available389C>GADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*28Not Available641A>TADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Cytochrome P450 2C9CYP2C9*33Not Available395G>A ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation. Details
Interactions
Drug Interactions
DrugInteractionDrug group
AbciximabAbciximab may increase the anticoagulant activities of Phenprocoumon.Approved
AbirateroneThe serum concentration of Phenprocoumon can be increased when it is combined with Abiraterone.Approved
AceclofenacAceclofenac may increase the anticoagulant activities of Phenprocoumon.Approved
AcenocoumarolPhenprocoumon may increase the anticoagulant activities of Acenocoumarol.Approved
AcetaminophenAcetaminophen may increase the anticoagulant activities of Phenprocoumon.Approved
AcetohexamideAcetohexamide may increase the anticoagulant activities of Phenprocoumon.Withdrawn
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
AdapaleneAdapalene may increase the anticoagulant activities of Phenprocoumon.Approved
AllopurinolAllopurinol may increase the anticoagulant activities of Phenprocoumon.Approved
AllylestrenolThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Allylestrenol.Approved
AlprostadilAlprostadil may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
AlteplaseAlteplase may increase the anticoagulant activities of Phenprocoumon.Approved
AmdinocillinAmdinocillin may increase the anticoagulant activities of Phenprocoumon.Withdrawn
AmineptineAmineptine may increase the anticoagulant activities of Phenprocoumon.Illicit, Withdrawn
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Phenprocoumon.Approved
AmiodaroneAmiodarone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
AmitriptylineAmitriptyline may increase the anticoagulant activities of Phenprocoumon.Approved
AmobarbitalThe metabolism of Phenprocoumon can be increased when combined with Amobarbital.Approved, Illicit
AmoxicillinAmoxicillin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
AmpicillinAmpicillin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
AnagrelideAnagrelide may increase the anticoagulant activities of Phenprocoumon.Approved
AncrodPhenprocoumon may increase the anticoagulant activities of Ancrod.Investigational
AndrographolideHMPL-004 may increase the anticoagulant activities of Phenprocoumon.Investigational
AnisodamineAnisodamine may increase the anticoagulant activities of Phenprocoumon.Investigational
AnistreplaseAnistreplase may increase the anticoagulant activities of Phenprocoumon.Approved
AntipyrineAntipyrine may increase the anticoagulant activities of Phenprocoumon.Approved
Antithrombin III humanPhenprocoumon may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanApixaban may increase the anticoagulant activities of Phenprocoumon.Approved
ApocyninAcetovanillone may increase the anticoagulant activities of Phenprocoumon.Investigational
ApremilastApremilast may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
AprepitantThe serum concentration of Phenprocoumon can be increased when it is combined with Aprepitant.Approved, Investigational
AprotininThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Aprotinin.Approved, Withdrawn
ArdeparinArdeparin may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
ArgatrobanArgatroban may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
AtazanavirThe metabolism of Phenprocoumon can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Phenprocoumon can be decreased when combined with Atomoxetine.Approved
AtorvastatinAtorvastatin may increase the anticoagulant activities of Phenprocoumon.Approved
AzapropazoneAzapropazone may increase the anticoagulant activities of Phenprocoumon.Withdrawn
AzathioprineAzathioprine may decrease the anticoagulant activities of Phenprocoumon.Approved
AzelastineAzelastine may increase the anticoagulant activities of Phenprocoumon.Approved
AzidocillinAzidocillin may increase the anticoagulant activities of Phenprocoumon.Approved
AzithromycinThe serum concentration of Phenprocoumon can be increased when it is combined with Azithromycin.Approved
AzlocillinAzlocillin may increase the anticoagulant activities of Phenprocoumon.Approved
BacampicillinBacampicillin may increase the anticoagulant activities of Phenprocoumon.Approved
BalsalazideBalsalazide may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
BarbexacloneThe metabolism of Phenprocoumon can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Phenprocoumon can be increased when combined with Barbital.Illicit
BazedoxifeneBazedoxifene may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
BecaplerminBecaplermin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
BemiparinBemiparin may increase the anticoagulant activities of Phenprocoumon.Approved
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Phenprocoumon.Withdrawn
Benzathine benzylpenicillinBenzathine benzylpenicillin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
BenzylpenicillinBenzylpenicillin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
Benzylpenicilloyl PolylysineBenzylpenicilloyl Polylysine may increase the anticoagulant activities of Phenprocoumon.Approved
BeraprostBeraprost may increase the anticoagulant activities of Phenprocoumon.Investigational
Betulinic AcidBetulinic Acid may increase the anticoagulant activities of Phenprocoumon.Investigational
BexaroteneThe serum concentration of Phenprocoumon can be decreased when it is combined with Bexarotene.Approved, Investigational
BezafibrateBezafibrate may increase the anticoagulant activities of Phenprocoumon.Approved
BicalutamideThe serum concentration of Phenprocoumon can be increased when it is combined with Bicalutamide.Approved
BivalirudinBivalirudin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
BoceprevirThe metabolism of Phenprocoumon can be decreased when combined with Boceprevir.Approved, Investigational
BortezomibThe metabolism of Phenprocoumon can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe metabolism of Phenprocoumon can be increased when combined with Bosentan.Approved, Investigational
BromfenacBromfenac may increase the anticoagulant activities of Phenprocoumon.Approved
BucillamineBucillamine may increase the anticoagulant activities of Phenprocoumon.Investigational
ButylphthalideButylphthalide may increase the anticoagulant activities of Phenprocoumon.Investigational
CangrelorCangrelor may increase the anticoagulant activities of Phenprocoumon.Approved
CapecitabineThe serum concentration of Phenprocoumon can be increased when it is combined with Capecitabine.Approved, Investigational
CarbamazepineThe serum concentration of Phenprocoumon can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarbenicillinCarbenicillin may increase the anticoagulant activities of Phenprocoumon.Approved
CarbimazoleCarbimazole may decrease the anticoagulant activities of Phenprocoumon.Approved
CarprofenCarprofen may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the anticoagulant activities of Phenprocoumon.Experimental
CefacetrileCefacetrile may increase the anticoagulant activities of Phenprocoumon.Approved
CefaclorCefaclor may increase the anticoagulant activities of Phenprocoumon.Approved
CefadroxilCefadroxil may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved, Withdrawn
CefalotinCefalotin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
CefamandoleCefamandole may increase the anticoagulant activities of Phenprocoumon.Approved
CefapirinCefapirin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
CefazolinCefazolin may increase the anticoagulant activities of Phenprocoumon.Approved
CefiximeCefixime may increase the anticoagulant activities of Phenprocoumon.Approved
CefmenoximeCefmenoxime may increase the anticoagulant activities of Phenprocoumon.Approved
CefmetazoleCefmetazole may increase the anticoagulant activities of Phenprocoumon.Approved
CefonicidCefonicid may increase the anticoagulant activities of Phenprocoumon.Approved
CefoperazoneCefoperazone may increase the anticoagulant activities of Phenprocoumon.Approved
CeforanideCeforanide may increase the anticoagulant activities of Phenprocoumon.Approved
CefotaximeCefotaxime may increase the anticoagulant activities of Phenprocoumon.Approved
CefotetanCefotetan may increase the anticoagulant activities of Phenprocoumon.Approved
CefotiamCefotiam may increase the anticoagulant activities of Phenprocoumon.Approved
CefoxitinCefoxitin may increase the anticoagulant activities of Phenprocoumon.Approved
CefpodoximeCefpodoxime may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
CefradineCefradine may increase the anticoagulant activities of Phenprocoumon.Approved
CefroxadineCefroxadine may increase the anticoagulant activities of Phenprocoumon.Withdrawn
CeftazidimeCeftazidime may increase the anticoagulant activities of Phenprocoumon.Approved
CeftizoximeCeftizoxime may increase the anticoagulant activities of Phenprocoumon.Approved
CeftriaxoneCeftriaxone may increase the anticoagulant activities of Phenprocoumon.Approved
CefuroximeCefuroxime may increase the anticoagulant activities of Phenprocoumon.Approved
CelecoxibCelecoxib may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
CephalexinCephalexin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
CephaloglycinCephaloglycin may increase the anticoagulant activities of Phenprocoumon.Approved
CephaloridineCephaloridine may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
CeritinibThe serum concentration of Phenprocoumon can be increased when it is combined with Ceritinib.Approved
CerivastatinCerivastatin may increase the anticoagulant activities of Phenprocoumon.Withdrawn
CertoparinPhenprocoumon may increase the anticoagulant activities of Certoparin.Approved
Chloral hydrateThe serum concentration of Phenprocoumon can be increased when it is combined with Chloral hydrate.Approved, Illicit, Vet Approved
ChloramphenicolChloramphenicol may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
ChloroquineChloroquine may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Phenprocoumon.Withdrawn
ChlorpropamideChlorpropamide may increase the anticoagulant activities of Phenprocoumon.Approved
ChlortetracyclineChlortetracycline may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
CholecalciferolThe metabolism of Phenprocoumon can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholestyramineCholestyramine can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Choline magnesium trisalicylateTrisalicylate-choline may increase the anticoagulant activities of Phenprocoumon.Approved
CilostazolCilostazol may increase the anticoagulant activities of Phenprocoumon.Approved
CimetidineCimetidine may increase the anticoagulant activities of Phenprocoumon.Approved
CinoxacinCinoxacin may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
CiprofloxacinCiprofloxacin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
CitalopramCitalopram may increase the anticoagulant activities of Phenprocoumon.Approved
Citric AcidPhenprocoumon may increase the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Phenprocoumon can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Phenprocoumon can be decreased when combined with Clemastine.Approved
ClofibrateClofibrate may increase the anticoagulant activities of Phenprocoumon.Approved
ClomipramineClomipramine may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
ClonixinClonixin may increase the anticoagulant activities of Phenprocoumon.Approved
ClopidogrelThe metabolism of Phenprocoumon can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Phenprocoumon can be decreased when combined with Clotrimazole.Approved, Vet Approved
CloxacillinCloxacillin may decrease the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
CobicistatThe metabolism of Phenprocoumon can be decreased when combined with Cobicistat.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ConivaptanThe serum concentration of Phenprocoumon can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated estrogensConjugated Equine Estrogens may decrease the anticoagulant activities of Phenprocoumon.Approved
CrizotinibThe metabolism of Phenprocoumon can be decreased when combined with Crizotinib.Approved
CurcuminCurcumin may increase the anticoagulant activities of Phenprocoumon.Investigational
CyclacillinCyclacillin may increase the anticoagulant activities of Phenprocoumon.Approved
CyclobenzaprineCyclobenzaprine may increase the anticoagulant activities of Phenprocoumon.Approved
CyclosporineThe metabolism of Phenprocoumon can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Phenprocoumon.Approved
DabrafenibThe serum concentration of Phenprocoumon can be decreased when it is combined with Dabrafenib.Approved
DalteparinPhenprocoumon may increase the anticoagulant activities of Dalteparin.Approved
DapoxetineDapoxetine may increase the anticoagulant activities of Phenprocoumon.Investigational
DarexabanPhenprocoumon may increase the anticoagulant activities of Ym150.Investigational
DarunavirThe metabolism of Phenprocoumon can be decreased when combined with Darunavir.Approved
DasatinibDasatinib may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
DeferasiroxThe serum concentration of Phenprocoumon can be decreased when it is combined with Deferasirox.Approved, Investigational
DefibrotideDefibrotide may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
DelavirdineThe metabolism of Phenprocoumon can be decreased when combined with Delavirdine.Approved
DemeclocyclineDemeclocycline may increase the anticoagulant activities of Phenprocoumon.Approved
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Deoxycholic Acid.Approved
DesipramineDesipramine may increase the anticoagulant activities of Phenprocoumon.Approved
DesirudinPhenprocoumon may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Phenprocoumon.Investigational
DesogestrelDesogestrel may decrease the anticoagulant activities of Phenprocoumon.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Phenprocoumon.Approved
DexamethasoneThe serum concentration of Phenprocoumon can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexmethylphenidateThe serum concentration of Phenprocoumon can be increased when it is combined with Dexmethylphenidate.Approved
DextranPhenprocoumon may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Phenprocoumon may increase the anticoagulant activities of Dextran 40.Approved
DiclofenacDiclofenac may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
DicloxacillinDicloxacillin may decrease the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
DicoumarolDicoumarol may increase the anticoagulant activities of Phenprocoumon.Approved
DienestrolDienestrol may decrease the anticoagulant activities of Phenprocoumon.Approved
DienogestDienogest may decrease the anticoagulant activities of Phenprocoumon.Approved
DiethylstilbestrolDiethylstilbestrol may decrease the anticoagulant activities of Phenprocoumon.Approved
DiflunisalDiflunisal may increase the anticoagulant activities of Phenprocoumon.Approved
DihydroergotamineThe metabolism of Phenprocoumon can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneDihydrotestosterone may increase the anticoagulant activities of Phenprocoumon.Illicit
DiltiazemThe metabolism of Phenprocoumon can be decreased when combined with Diltiazem.Approved
DipyridamoleDipyridamole may increase the anticoagulant activities of Phenprocoumon.Approved
DisulfiramThe serum concentration of Phenprocoumon can be increased when it is combined with Disulfiram.Approved
DitazoleDitazole may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
DosulepinDosulepin may increase the anticoagulant activities of Phenprocoumon.Approved
DoxepinDoxepin may increase the anticoagulant activities of Phenprocoumon.Approved
DoxycyclineThe metabolism of Phenprocoumon can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Phenprocoumon can be increased when it is combined with Dronedarone.Approved
DrospirenoneDrospirenone may decrease the anticoagulant activities of Phenprocoumon.Approved
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational, Withdrawn
DroxicamDroxicam may increase the anticoagulant activities of Phenprocoumon.Approved
DuloxetineDuloxetine may increase the anticoagulant activities of Phenprocoumon.Approved
DuvelisibDuvelisib may increase the anticoagulant activities of Phenprocoumon.Investigational
DydrogesteroneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Dydrogesterone.Approved, Withdrawn
E-6201E6201 may increase the anticoagulant activities of Phenprocoumon.Investigational
EbselenEbselen may increase the anticoagulant activities of Phenprocoumon.Investigational
EconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Econazole.Approved
Edetic AcidPhenprocoumon may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanEdoxaban may increase the anticoagulant activities of Phenprocoumon.Approved
EfavirenzThe serum concentration of Phenprocoumon can be decreased when it is combined with Efavirenz.Approved, Investigational
EnoxacinEnoxacin may increase the anticoagulant activities of Phenprocoumon.Approved
EnoxaparinPhenprocoumon may increase the anticoagulant activities of Enoxaparin.Approved
EnzalutamideThe serum concentration of Phenprocoumon can be decreased when it is combined with Enzalutamide.Approved
EpinastineEpinastine may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
EpirizoleEpirizole may increase the anticoagulant activities of Phenprocoumon.Approved
EpoprostenolEpoprostenol may increase the anticoagulant activities of Phenprocoumon.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
EquolS Equol may decrease the anticoagulant activities of Phenprocoumon.Investigational
ErythromycinThe metabolism of Phenprocoumon can be decreased when combined with Erythromycin.Approved, Vet Approved
ErythromycinThe serum concentration of Phenprocoumon can be increased when it is combined with Erythromycin.Approved, Vet Approved
EscitalopramEscitalopram may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Phenprocoumon can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsmirtazapineEsmirtazapine may increase the anticoagulant activities of Phenprocoumon.Investigational
EsomeprazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Esomeprazole.Approved, Investigational
EstradiolEstradiol may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational, Vet Approved
EstramustineEstramustine may decrease the anticoagulant activities of Phenprocoumon.Approved
EstriolEstriol may decrease the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
Estrogens, esterifiedEstrogens, esterified may decrease the anticoagulant activities of Phenprocoumon.Approved
EstroneEstrone may decrease the anticoagulant activities of Phenprocoumon.Approved
Estrone sulfateEstrone sulfate may decrease the anticoagulant activities of Phenprocoumon.Approved
Etacrynic acidThe serum concentration of Phenprocoumon can be increased when it is combined with Etacrynic acid.Approved
EtanerceptEtanercept may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
EthanolThe serum concentration of Phenprocoumon can be decreased when it is combined with Ethanol.Approved
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Phenprocoumon.Approved
EthotoinEthotoin may increase the anticoagulant activities of Phenprocoumon.Approved
Ethyl biscoumacetatePhenprocoumon may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Ethynodiol diacetateEthynodiol diacetate may decrease the anticoagulant activities of Phenprocoumon.Approved
EtodolacEtodolac may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the anticoagulant activities of Phenprocoumon.Approved
EtofibrateEtofibrate may increase the anticoagulant activities of Phenprocoumon.Approved
EtonogestrelEtonogestrel may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
EtoperidoneEtoperidone may increase the anticoagulant activities of Phenprocoumon.Approved
EtoposideEtoposide may increase the anticoagulant activities of Phenprocoumon.Approved
EtoricoxibEtoricoxib may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
EtravirineThe serum concentration of Phenprocoumon can be decreased when it is combined with Etravirine.Approved
ExenatideExenatide may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
FelodipineThe metabolism of Phenprocoumon can be decreased when combined with Felodipine.Approved, Investigational
FenbufenFenbufen may increase the anticoagulant activities of Phenprocoumon.Approved
FenofibrateFenofibrate may increase the anticoagulant activities of Phenprocoumon.Approved
FenoprofenFenoprofen may increase the anticoagulant activities of Phenprocoumon.Approved
FibrinolysinPlasmin may increase the anticoagulant activities of Phenprocoumon.Investigational
FleroxacinFleroxacin may increase the anticoagulant activities of Phenprocoumon.Approved
FloctafenineFloctafenine may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
FloxuridineThe metabolism of Phenprocoumon can be decreased when combined with Floxuridine.Approved
FlucloxacillinFlucloxacillin may decrease the anticoagulant activities of Phenprocoumon.Approved
FluconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Fluconazole.Approved
FluindionePhenprocoumon may increase the anticoagulant activities of Fluindione.Investigational
FlumequineFlumequine may increase the anticoagulant activities of Phenprocoumon.Withdrawn
FluorouracilThe serum concentration of Phenprocoumon can be increased when it is combined with Fluorouracil.Approved
FluorouracilThe metabolism of Phenprocoumon can be decreased when combined with Fluorouracil.Approved
FluoxetineFluoxetine may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
FluoxymesteroneFluoxymesterone may increase the anticoagulant activities of Phenprocoumon.Approved, Illicit
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
FluvastatinThe metabolism of Phenprocoumon can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Phenprocoumon can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxPhenprocoumon may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumFondaparinux sodium may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
FosamprenavirThe metabolism of Phenprocoumon can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Phenprocoumon can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinFosphenytoin may increase the anticoagulant activities of Phenprocoumon.Approved
Fusidic AcidThe serum concentration of Phenprocoumon can be increased when it is combined with Fusidic Acid.Approved
GabexatePhenprocoumon may increase the anticoagulant activities of Gabexate.Investigational
GatifloxacinGatifloxacin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
GefitinibGefitinib may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
GemfibrozilGemfibrozil may increase the anticoagulant activities of Phenprocoumon.Approved
GemifloxacinGemifloxacin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
GenisteinGenistein may decrease the anticoagulant activities of Phenprocoumon.Investigational
GestodeneGestodene may decrease the anticoagulant activities of Phenprocoumon.Approved
GestrinoneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Gestrinone.Approved
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Ginkgo biloba is combined with Phenprocoumon.Approved, Nutraceutical
GlibornurideGlibornuride may increase the anticoagulant activities of Phenprocoumon.Withdrawn
GliclazideGliclazide may increase the anticoagulant activities of Phenprocoumon.Approved
GlimepirideGlimepiride may increase the anticoagulant activities of Phenprocoumon.Approved
GlipizideGlipizide may increase the anticoagulant activities of Phenprocoumon.Approved
GliquidoneGliquidone may increase the anticoagulant activities of Phenprocoumon.Approved
GlisoxepideGlisoxepide may increase the anticoagulant activities of Phenprocoumon.Approved
Glucagon recombinantGlucagon recombinant may increase the anticoagulant activities of Phenprocoumon.Approved
GlutethimideThe metabolism of Phenprocoumon can be increased when combined with Glutethimide.Approved, Illicit
GlyburideGlyburide may increase the anticoagulant activities of Phenprocoumon.Approved
GrepafloxacinGrepafloxacin may increase the anticoagulant activities of Phenprocoumon.Withdrawn
GriseofulvinThe serum concentration of Phenprocoumon can be decreased when it is combined with Griseofulvin.Approved, Vet Approved
HeminHemin may increase the anticoagulant activities of Phenprocoumon.Approved
HeparinPhenprocoumon may increase the anticoagulant activities of Heparin.Approved, Investigational
HexestrolHexestrol may decrease the anticoagulant activities of Phenprocoumon.Withdrawn
HexobarbitalThe metabolism of Phenprocoumon can be increased when combined with Hexobarbital.Approved
HigenamineHigenamine may increase the anticoagulant activities of Phenprocoumon.Investigational
Hydroxyprogesterone caproateThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Phenprocoumon.Approved
IbudilastIbudilast may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
IbuprofenIbuprofen may increase the anticoagulant activities of Phenprocoumon.Approved
IbuproxamIbuproxam may increase the anticoagulant activities of Phenprocoumon.Withdrawn
IcatibantIcatibant may increase the anticoagulant activities of Phenprocoumon.Approved
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Phenprocoumon.Approved, Nutraceutical
IdelalisibThe serum concentration of Phenprocoumon can be increased when it is combined with Idelalisib.Approved
IfenprodilIfenprodil may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
IfosfamideIfosfamide may increase the anticoagulant activities of Phenprocoumon.Approved
IloprostIloprost may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
ImatinibThe metabolism of Phenprocoumon can be decreased when combined with Imatinib.Approved
ImipramineImipramine may increase the anticoagulant activities of Phenprocoumon.Approved
IndalpineIndalpine may increase the anticoagulant activities of Phenprocoumon.Investigational, Withdrawn
IndinavirThe metabolism of Phenprocoumon can be decreased when combined with Indinavir.Approved
IndobufenIndobufen may increase the anticoagulant activities of Phenprocoumon.Investigational
IndomethacinIndomethacin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
IndoprofenIndoprofen may increase the anticoagulant activities of Phenprocoumon.Withdrawn
IrbesartanThe metabolism of Phenprocoumon can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Phenprocoumon can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoxicamIsoxicam may increase the anticoagulant activities of Phenprocoumon.Withdrawn
IsradipineThe metabolism of Phenprocoumon can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Phenprocoumon can be increased when it is combined with Ivacaftor.Approved
IvermectinIvermectin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
JosamycinThe serum concentration of Phenprocoumon can be increased when it is combined with Josamycin.Approved
KebuzoneKebuzone may increase the anticoagulant activities of Phenprocoumon.Experimental
KetanserinKetanserin may increase the anticoagulant activities of Phenprocoumon.Investigational
KetoconazoleThe metabolism of Phenprocoumon can be decreased when combined with Ketoconazole.Approved, Investigational
KetoconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Ketoconazole.Approved, Investigational
KetoprofenKetoprofen may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
KetorolacKetorolac may increase the anticoagulant activities of Phenprocoumon.Approved
KitasamycinThe serum concentration of Phenprocoumon can be increased when it is combined with Kitasamycin.Experimental
L-CarnitineL-Carnitine may increase the anticoagulant activities of Phenprocoumon.Approved
LansoprazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe metabolism of Phenprocoumon can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideLeflunomide may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
LepirudinLepirudin may increase the anticoagulant activities of Phenprocoumon.Approved
LevofloxacinLevofloxacin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Phenprocoumon.Approved
LevonorgestrelLevonorgestrel may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
LevothyroxineLevothyroxine may increase the anticoagulant activities of Phenprocoumon.Approved
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Phenprocoumon.Approved
LiothyronineLiothyronine may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
LiotrixLiotrix may increase the anticoagulant activities of Phenprocoumon.Approved
LisofyllineLisofylline may increase the anticoagulant activities of Phenprocoumon.Investigational
LixisenatideLixisenatide can cause a decrease in the absorption of Phenprocoumon resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
LomefloxacinLomefloxacin may increase the anticoagulant activities of Phenprocoumon.Approved
LopinavirThe metabolism of Phenprocoumon can be decreased when combined with Lopinavir.Approved
LornoxicamLornoxicam may increase the anticoagulant activities of Phenprocoumon.Approved
LosartanThe metabolism of Phenprocoumon can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Phenprocoumon can be decreased when combined with Lovastatin.Approved, Investigational
LoxoprofenLoxoprofen may increase the anticoagulant activities of Phenprocoumon.Approved
LuliconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Phenprocoumon can be increased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
LynestrenolLynestrenol may decrease the anticoagulant activities of Phenprocoumon.Investigational
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Phenprocoumon.Approved
MasoprocolMasoprocol may increase the anticoagulant activities of Phenprocoumon.Approved
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
MedrogestoneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Medrogestone.Approved
Medroxyprogesterone acetateMedroxyprogesterone acetate may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Phenprocoumon.Approved
Megestrol acetateThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Megestrol acetate.Approved, Vet Approved
MeloxicamMeloxicam may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
MercaptopurineMercaptopurine may decrease the anticoagulant activities of Phenprocoumon.Approved
MesalazineMesalazine may increase the anticoagulant activities of Phenprocoumon.Approved
MestranolMestranol may decrease the anticoagulant activities of Phenprocoumon.Approved
MetamizoleMetamizole may increase the anticoagulant activities of Phenprocoumon.Withdrawn
MethallenestrilMethallenestril may decrease the anticoagulant activities of Phenprocoumon.Experimental
MethimazoleMethimazole may decrease the anticoagulant activities of Phenprocoumon.Approved
MethohexitalThe metabolism of Phenprocoumon can be increased when combined with Methohexital.Approved
MethylphenidateThe serum concentration of Phenprocoumon can be increased when it is combined with Methylphenidate.Approved, Investigational
MethylphenobarbitalThe metabolism of Phenprocoumon can be increased when combined with Methylphenobarbital.Approved
MethyltestosteroneMethyltestosterone may increase the anticoagulant activities of Phenprocoumon.Approved
MeticillinMeticillin may increase the anticoagulant activities of Phenprocoumon.Approved
MetronidazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Metronidazole.Approved
MevastatinMevastatin may increase the anticoagulant activities of Phenprocoumon.Experimental
MezlocillinMezlocillin may increase the anticoagulant activities of Phenprocoumon.Approved
MiconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MifepristoneThe serum concentration of Phenprocoumon can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Phenprocoumon.Approved
MilrinoneMilrinone may increase the anticoagulant activities of Phenprocoumon.Approved
MinocyclineMinocycline may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
MirtazapineMirtazapine may increase the anticoagulant activities of Phenprocoumon.Approved
MitotaneThe serum concentration of Phenprocoumon can be decreased when it is combined with Mitotane.Approved
MizoribineMizoribine may increase the anticoagulant activities of Phenprocoumon.Investigational
ModafinilThe serum concentration of Phenprocoumon can be decreased when it is combined with Modafinil.Approved, Investigational
MoxifloxacinMoxifloxacin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Phenprocoumon.Approved
NabumetoneNabumetone may increase the anticoagulant activities of Phenprocoumon.Approved
NadroparinPhenprocoumon may increase the anticoagulant activities of Nadroparin.Approved
NafamostatNafamostat may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
NafcillinNafcillin may decrease the anticoagulant activities of Phenprocoumon.Approved
NaftifineNaftifine may increase the anticoagulant activities of Phenprocoumon.Approved
NaftopidilNaftopidil may increase the anticoagulant activities of Phenprocoumon.Investigational
Nalidixic AcidNalidixic Acid may increase the anticoagulant activities of Phenprocoumon.Approved
NaproxenNaproxen may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
NCX 4016NCX 4016 may increase the anticoagulant activities of Phenprocoumon.Investigational
NefazodoneThe metabolism of Phenprocoumon can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Phenprocoumon can be decreased when combined with Nelfinavir.Approved
NeomycinNeomycin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
NepafenacNepafenac may increase the anticoagulant activities of Phenprocoumon.Approved
NetupitantThe serum concentration of Phenprocoumon can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Phenprocoumon can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Phenprocoumon can be decreased when combined with Nicardipine.Approved
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Phenprocoumon.Approved
NilotinibThe metabolism of Phenprocoumon can be decreased when combined with Nilotinib.Approved, Investigational
NimesulideNimesulide may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
NintedanibThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Nintedanib.Approved
NitroaspirinNitroaspirin may increase the anticoagulant activities of Phenprocoumon.Investigational
NorelgestrominNorelgestromin may decrease the anticoagulant activities of Phenprocoumon.Approved
NorethisteroneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Norethisterone.Approved
NorfloxacinNorfloxacin may increase the anticoagulant activities of Phenprocoumon.Approved
NorgestimateNorgestimate may decrease the anticoagulant activities of Phenprocoumon.Approved
NorgestrelNorgestrel may decrease the anticoagulant activities of Phenprocoumon.Approved
NortriptylineNortriptyline may increase the anticoagulant activities of Phenprocoumon.Approved
ObinutuzumabThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Obinutuzumab.Approved
OfloxacinOfloxacin may increase the anticoagulant activities of Phenprocoumon.Approved
OlaparibThe metabolism of Phenprocoumon can be decreased when combined with Olaparib.Approved
OlopatadineOlopatadine may increase the anticoagulant activities of Phenprocoumon.Approved
OlsalazineOlsalazine may increase the anticoagulant activities of Phenprocoumon.Approved
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Omacetaxine mepesuccinate.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Phenprocoumon.Approved, Nutraceutical
OmeprazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OpipramolOpipramol may increase the anticoagulant activities of Phenprocoumon.Investigational
OritavancinThe serum concentration of Phenprocoumon can be increased when it is combined with Oritavancin.Approved, Investigational
OsimertinibThe serum concentration of Phenprocoumon can be increased when it is combined with Osimertinib.Approved
OxacillinOxacillin may increase the anticoagulant activities of Phenprocoumon.Approved
OxandroloneOxandrolone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
OxaprozinOxaprozin may increase the anticoagulant activities of Phenprocoumon.Approved
OxymetholoneOxymetholone may increase the anticoagulant activities of Phenprocoumon.Approved, Illicit
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Phenprocoumon.Withdrawn
OxytetracyclineOxytetracycline may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
OzagrelKct 0809 may increase the anticoagulant activities of Phenprocoumon.Investigational
PalbociclibThe serum concentration of Phenprocoumon can be increased when it is combined with Palbociclib.Approved
ParecoxibParecoxib may increase the anticoagulant activities of Phenprocoumon.Approved
ParnaparinParnaparin may increase the anticoagulant activities of Phenprocoumon.Approved
ParoxetineParoxetine may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PazufloxacinPazufloxacin may increase the anticoagulant activities of Phenprocoumon.Investigational
PefloxacinPefloxacin may increase the anticoagulant activities of Phenprocoumon.Approved
PentobarbitalThe metabolism of Phenprocoumon can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Phenprocoumon.Approved
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenindionePhenindione may increase the anticoagulant activities of Phenprocoumon.Approved
PhenobarbitalThe metabolism of Phenprocoumon can be increased when combined with Phenobarbital.Approved
PhenoxymethylpenicillinPhenoxymethylpenicillin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
PhenytoinPhenytoin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
PhylloquinonePhylloquinone may decrease the anticoagulant activities of Phenprocoumon.Approved
PimecrolimusPimecrolimus may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PioglitazoneThe metabolism of Phenprocoumon can be decreased when combined with Pioglitazone.Approved, Investigational
PiperacillinPiperacillin may increase the anticoagulant activities of Phenprocoumon.Approved
PirfenidonePirfenidone may increase the anticoagulant activities of Phenprocoumon.Investigational
PiroxicamPiroxicam may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PitavastatinPitavastatin may increase the anticoagulant activities of Phenprocoumon.Approved
PivampicillinPivampicillin may increase the anticoagulant activities of Phenprocoumon.Approved
PivmecillinamPivmecillinam may increase the anticoagulant activities of Phenprocoumon.Approved
PosaconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrasugrelPrasugrel may increase the anticoagulant activities of Phenprocoumon.Approved
PravastatinPravastatin may increase the anticoagulant activities of Phenprocoumon.Approved
PrimidoneThe metabolism of Phenprocoumon can be increased when combined with Primidone.Approved, Vet Approved
Procaine benzylpenicillinProcaine benzylpenicillin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
ProgesteroneThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Progesterone.Approved, Vet Approved
PromestrienePromestriene may decrease the anticoagulant activities of Phenprocoumon.Investigational
PropacetamolPropacetamol may increase the anticoagulant activities of Phenprocoumon.Approved
PropafenoneThe serum concentration of Phenprocoumon can be increased when it is combined with Propafenone.Approved
PropylthiouracilPropylthiouracil may decrease the anticoagulant activities of Phenprocoumon.Approved
Protein S humanPhenprocoumon may increase the anticoagulant activities of Protein S human.Approved
ProtriptylineProtriptyline may increase the anticoagulant activities of Phenprocoumon.Approved
PrulifloxacinPrulifloxacin may increase the anticoagulant activities of Phenprocoumon.Investigational
PTC299PTC299 may increase the anticoagulant activities of Phenprocoumon.Investigational
PyrimethamineThe metabolism of Phenprocoumon can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinestrolQuinestrol may decrease the anticoagulant activities of Phenprocoumon.Approved
QuinidineQuinidine may increase the anticoagulant activities of Phenprocoumon.Approved
QuinineQuinine may increase the anticoagulant activities of Phenprocoumon.Approved
RabeprazoleThe metabolism of Phenprocoumon can be decreased when combined with Rabeprazole.Approved, Investigational
RamatrobanRamatroban may increase the anticoagulant activities of Phenprocoumon.Investigational
RanolazineThe metabolism of Phenprocoumon can be decreased when combined with Ranolazine.Approved, Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Phenprocoumon.Experimental, Investigational
ReteplaseReteplase may increase the anticoagulant activities of Phenprocoumon.Approved
ReviparinPhenprocoumon may increase the anticoagulant activities of Reviparin.Approved
RidogrelRidogrel may increase the anticoagulant activities of Phenprocoumon.Approved
RifabutinThe metabolism of Phenprocoumon can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Phenprocoumon can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Phenprocoumon can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Phenprocoumon can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanPhenprocoumon may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the anticoagulant activities of Phenprocoumon.Investigational, Withdrawn
RosiglitazoneRosiglitazone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
RosoxacinRosoxacin may increase the anticoagulant activities of Phenprocoumon.Approved
RosuvastatinRosuvastatin may increase the anticoagulant activities of Phenprocoumon.Approved
SalicylamideSalicylamide may increase the anticoagulant activities of Phenprocoumon.Approved
Salicylic acidSalicylic acid may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
SalsalateSalsalate may increase the anticoagulant activities of Phenprocoumon.Approved
SaquinavirThe metabolism of Phenprocoumon can be decreased when combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Phenprocoumon can be increased when combined with Secobarbital.Approved, Vet Approved
SecoisolariciresinolSecoisolariciresinol may decrease the anticoagulant activities of Phenprocoumon.Investigational
SelexipagSelexipag may increase the anticoagulant activities of Phenprocoumon.Approved
SertralineSertraline may increase the anticoagulant activities of Phenprocoumon.Approved
SevofluraneSevoflurane may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
SildenafilThe metabolism of Phenprocoumon can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Phenprocoumon can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Phenprocoumon can be increased when it is combined with Simeprevir.Approved
SimvastatinSimvastatin may increase the anticoagulant activities of Phenprocoumon.Approved
SolithromycinThe serum concentration of Phenprocoumon can be increased when it is combined with Solithromycin.Investigational
SorafenibThe metabolism of Phenprocoumon can be decreased when combined with Sorafenib.Approved, Investigational
SparfloxacinSparfloxacin may increase the anticoagulant activities of Phenprocoumon.Approved
SRT501SRT501 may increase the anticoagulant activities of Phenprocoumon.Investigational
St. John's WortThe metabolism of Phenprocoumon can be increased when combined with St. John's Wort.Nutraceutical
StanozololStanozolol may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
StiripentolThe serum concentration of Phenprocoumon can be increased when it is combined with Stiripentol.Approved
StreptokinaseStreptokinase may increase the anticoagulant activities of Phenprocoumon.Approved
SucralfateSucralfate may decrease the anticoagulant activities of Phenprocoumon.Approved
SugammadexSugammadex may increase the anticoagulant activities of Phenprocoumon.Approved
SulbactamSulbactam may increase the anticoagulant activities of Phenprocoumon.Approved
SulfadiazineThe metabolism of Phenprocoumon can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleSulfamethoxazole may increase the anticoagulant activities of Phenprocoumon.Approved
SulfasalazineSulfasalazine may increase the anticoagulant activities of Phenprocoumon.Approved
SulfinpyrazoneThe metabolism of Phenprocoumon can be decreased when combined with Sulfinpyrazone.Approved
SulfisoxazoleThe metabolism of Phenprocoumon can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulindacSulindac may increase the anticoagulant activities of Phenprocoumon.Approved
SulodexidePhenprocoumon may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SultamicillinSultamicillin may increase the anticoagulant activities of Phenprocoumon.Investigational
SuprofenSuprofen may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Phenprocoumon.Approved
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Phenprocoumon.Approved
TamoxifenThe serum concentration of Phenprocoumon can be increased when it is combined with Tamoxifen.Approved
TazobactamTazobactam may increase the anticoagulant activities of Phenprocoumon.Approved
TegafurThe serum concentration of Phenprocoumon can be increased when it is combined with Tegafur.Approved
TelaprevirThe metabolism of Phenprocoumon can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Phenprocoumon can be decreased when combined with Telithromycin.Approved
TemafloxacinTemafloxacin may increase the anticoagulant activities of Phenprocoumon.Withdrawn
TenecteplaseTenecteplase may increase the anticoagulant activities of Phenprocoumon.Approved
TenoxicamTenoxicam may increase the anticoagulant activities of Phenprocoumon.Approved
TeriflunomideTeriflunomide may increase the anticoagulant activities of Phenprocoumon.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Phenprocoumon.Investigational
TestosteroneTestosterone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
TetracyclineTetracycline may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
ThiamylalThe metabolism of Phenprocoumon can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Phenprocoumon can be increased when combined with Thiopental.Approved, Vet Approved
Thyroid, porcineThyroid, porcine may increase the anticoagulant activities of Phenprocoumon.Approved
TianeptineTianeptine may increase the anticoagulant activities of Phenprocoumon.Approved
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Phenprocoumon.Approved
TiboloneTibolone may increase the anticoagulant activities of Phenprocoumon.Approved
TicagrelorThe metabolism of Phenprocoumon can be decreased when combined with Ticagrelor.Approved
TicarcillinTicarcillin may increase the anticoagulant activities of Phenprocoumon.Approved, Vet Approved
TiclopidineThe metabolism of Phenprocoumon can be decreased when combined with Ticlopidine.Approved
TinoridineTinoridine may increase the anticoagulant activities of Phenprocoumon.Investigational
TinzaparinTinzaparin may increase the anticoagulant activities of Phenprocoumon.Approved
TipranavirTipranavir may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Phenprocoumon.Approved
TocilizumabThe serum concentration of Phenprocoumon can be decreased when it is combined with Tocilizumab.Approved
TolazamideTolazamide may increase the anticoagulant activities of Phenprocoumon.Approved
TolbutamideThe metabolism of Phenprocoumon can be decreased when combined with Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Phenprocoumon.Approved
TolmetinTolmetin may increase the anticoagulant activities of Phenprocoumon.Approved
ToremifeneToremifene may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
TositumomabThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Tositumomab.Approved
TramadolTramadol may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
TranilastTranilast may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
TrapidilTrapidil may increase the anticoagulant activities of Phenprocoumon.Approved
TreprostinilTreprostinil may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
TriflusalTriflusal may increase the anticoagulant activities of Phenprocoumon.Approved
TrimethoprimThe metabolism of Phenprocoumon can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineTrimipramine may increase the anticoagulant activities of Phenprocoumon.Approved
TrovafloxacinTrovafloxacin may increase the anticoagulant activities of Phenprocoumon.Approved, Withdrawn
UbidecarenoneCoenzyme Q10 may decrease the anticoagulant activities of Phenprocoumon.Experimental
UrokinaseUrokinase may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational, Withdrawn
ValdecoxibValdecoxib may increase the anticoagulant activities of Phenprocoumon.Investigational, Withdrawn
Valproic AcidThe metabolism of Phenprocoumon can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Phenprocoumon can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Phenprocoumon.Approved
VerapamilThe metabolism of Phenprocoumon can be decreased when combined with Verapamil.Approved
Vitamin EVitamin E may increase the anticoagulant activities of Phenprocoumon.Approved, Nutraceutical, Vet Approved
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Phenprocoumon.Approved
VoriconazoleThe serum concentration of Phenprocoumon can be increased when it is combined with Voriconazole.Approved, Investigational
VorinostatVorinostat may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
WarfarinWarfarin may increase the anticoagulant activities of Phenprocoumon.Approved
XimelagatranPhenprocoumon may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
ZafirlukastThe serum concentration of Phenprocoumon can be increased when it is combined with Zafirlukast.Approved, Investigational
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Phenprocoumon.Approved
ZileutonZileuton may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational, Withdrawn
ZimelidineZimelidine may increase the anticoagulant activities of Phenprocoumon.Withdrawn
ZiprasidoneThe metabolism of Phenprocoumon can be decreased when combined with Ziprasidone.Approved
ZomepiracZomepirac may increase the anticoagulant activities of Phenprocoumon.Withdrawn
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesB01AA04 — Phenprocoumon
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableMalignant Melanoma, Neoplasms1
2TerminatedTreatmentHaemorrhage / Thrombosis1
3Not Yet RecruitingTreatmentEnd-Stage Kidney Disease / Nonvalvular Atrial Fibrillation1
3Not Yet RecruitingTreatmentNonvalvular Atrial Fibrillation1
3TerminatedTreatmentNeoplasms / Venous Thromboembolism1
3Unknown StatusNot AvailableDeep Venous Thrombosis1
4Active Not RecruitingTreatmentNonvalvular Atrial Fibrillation1
4CompletedBasic ScienceAcute Coronary Syndromes (ACS) / Nonvalvular Atrial Fibrillation1
4CompletedTreatmentHip Replacement Postoperative / Knee Replacement Postoperative / Nonvalvular Atrial Fibrillation / Prophylaxis of Pulmonary embolism1
4CompletedTreatmentNonvalvular Atrial Fibrillation1
4RecruitingBasic ScienceAtrial Fibrillation or Pulmonary Embolism / Existent Coronary or Valvular Calcification, or Both and Agatston Score > 50 in at Least One Location / Need of Long Term Oral Anticoagulation Therapy (OAT)1
4RecruitingTreatment(Atrial Fibrillation) or (Atrial Flutter) / Thrombosis of Left Atrial Appendage1
4RecruitingTreatmentCervical Artery Dissection1
4RecruitingTreatmentLeft Atrial Thrombosis / Nonvalvular Atrial Fibrillation1
4TerminatedTreatmentAcute Coronary Syndromes (ACS) / Atherosclerosis / Coronary Heart Disease (CHD) / Nonvalvular Atrial Fibrillation1
4TerminatedTreatmentMechanical Heart Valve Recipients1
4WithdrawnTreatmentCoronary Heart Disease (CHD) / Non ST Segment Elevation Myocardial Infarction (NSTEMI) / ST Elevation Myocardial Infarction (STEMI) / Stable Angina (SA) / Unstable Angina (UA)1
Not AvailableActive Not RecruitingNot AvailableNonvalvular Atrial Fibrillation1
Not AvailableCompletedNot AvailableNonvalvular Atrial Fibrillation2
Not AvailableRecruitingNot AvailableUnsuspected Pulmonary Embolism1
Pharmacoeconomics
Manufacturers
  • Organon usa inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)179.5 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 )
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
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
Direct Parent4-hydroxycoumarins
Alternative Parents1-benzopyrans / Phenylpropanes / Pyranones and derivatives / Vinylogous acids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents4-hydroxycoumarin / Benzopyran / 1-benzopyran / Phenylpropane / Pyranone / Monocyclic benzene moiety / Benzenoid / Pyran / Heteroaromatic compound / Vinylogous acid
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorshydroxycoumarin (CHEBI:50438 )

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 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:54