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Identification
NameAcenocoumarol
Accession NumberDB01418
TypeSmall Molecule
GroupsApproved
DescriptionAcenocoumarol is a coumarin derivative used as an anticoagulant. Coumarin derivatives inhibit the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of vitamin K-dependent clotting factors, II, VII, XI and X, and interferes with coagulation. Hematocrit, hemoglobin, international normalized ratio and liver panel should be monitored. Patients on acenocoumarol are prohibited from giving blood.
Structure
Thumb
Synonyms
3-(alpha-(4'-Nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin
3-(alpha-(P-Nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin
3-(alpha-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin
3-(alpha-Acetonyl-P-nitrobenzyl)-4-hydroxycoumarin
3-(alpha-P-Nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin
4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-one
4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
Acenocoumarin
Acenocoumarolum
Acenocumarol
Acenocumarolo
Acenokumarin
Nicoumalone
Nicumalon
Nitrophenylacetylethyl-4-hydroxycoumarine
Nitrovarfarian
Nitrowarfarin
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SintromTablet4 mgOralPaladin Labs Inc1957-12-31Not applicableCanada
SintromTablet1 mgOralPaladin Labs Inc1962-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AscumarStar
Mini-sintromNot Available
SinkumarNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIII6WP63U32H
CAS number152-72-7
WeightAverage: 353.3255
Monoisotopic: 353.089937217
Chemical FormulaC19H15NO6
InChI KeyVABCILAOYCMVPS-UHFFFAOYSA-N
InChI
InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3
IUPAC Name
4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
SMILES
CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O
Pharmacology
IndicationFor the treatment and prevention of thromboembolic diseases. More specifically, it is indicated for the for the prevention of cerebral embolism, deep vein thrombosis, pulmonary embolism, thromboembolism in infarction and transient ischemic attacks. It is used for the treatment of deep vein thrombosis and myocardial infarction.
Structured Indications
PharmacodynamicsAcenocoumarol inhibits the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of certain glutamic acid residues near the N-terminals of clotting factors II, VII, IX and X, the vitamin K-dependent clotting factors. Glutamic acid carboxylation is important for the interaction between these clotting factors and calcium. Without this interaction, clotting cannot occur. Both the extrinsic (via factors VII, X and II) and intrinsic (via factors IX, X and II) are affected by acenocoumarol.
Mechanism of actionAcenocoumarol 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 clotting factors, 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 resulting 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
AbsorptionRapidly absorbed orally with greater than 60% bioavailability. Peak plasma levels are attained 1 to 3 hours following oral administration.
Volume of distribution

The volume of distribution at steady-state appeared to be significantly dose dependent: 78 ml/kg for doses < or = 20 microg/kg and 88 ml/kg for doses > 20 microg/kg respectively

Protein binding98.7% protein bound, mainly to albumin
Metabolism

Extensively metabolized in the liver via oxidation forming two hydroxy metabolites and keto reduction producing two alcohol metabolites. Reduction of the nitro group produces an amino metabolite which is further transformed to an acetoamido metabolite. Metabolites do not appear to be pharmacologically active.

SubstrateEnzymesProduct
Acenocoumarol
6-Hydroxy-R-acenocoumarolDetails
Acenocoumarol
7-Hydroxy-R-acenocoumarolDetails
Acenocoumarol
8-Hydroxy-R-acenocoumarolDetails
Route of eliminationMostly via the kidney as metabolites
Half life8 to 11 hours.
ClearanceNot Available
ToxicityThe onset and severity of the symptoms are dependent on the individual's sensitivity to oral anticoagulants, the severity of the overdosage, and the duration of treatment. Bleeding is the major sign of toxicity with oral anticoagulant drugs. The most frequent symptoms observed are: cutaneous bleeding (80%), haematuria (with renal colic) (52%), haematomas, gastrointestinal bleeding, haematemesis, uterine bleeding, epistaxis, gingival bleeding and bleeding into the joints. Further symptoms include tachycardia, hypotension, peripheral circulatory disorders due to loss of blood, nausea, vomiting, diarrhoea and abdominal pains.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Acenocoumarol Action PathwayDrug actionSMP00269
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbciximabAbciximab may increase the anticoagulant activities of Acenocoumarol.Approved
AbirateroneThe serum concentration of Acenocoumarol can be increased when it is combined with Abiraterone.Approved
AceclofenacAceclofenac may increase the anticoagulant activities of Acenocoumarol.Approved
AcetaminophenAcetaminophen may increase the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideAcetohexamide may increase the anticoagulant activities of Acenocoumarol.Withdrawn
AcetovanilloneAcetovanillone may increase the anticoagulant activities of Acenocoumarol.Investigational
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
AdapaleneAdapalene may increase the anticoagulant activities of Acenocoumarol.Approved
AllopurinolAllopurinol may increase the anticoagulant activities of Acenocoumarol.Approved
AllylestrenolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Allylestrenol.Approved
AlprostadilAlprostadil may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AlteplaseAlteplase may increase the anticoagulant activities of Acenocoumarol.Approved
AltrenogestThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Altrenogest.Vet Approved
ALX-0081ALX-0081 may increase the anticoagulant activities of Acenocoumarol.Investigational
AmdinocillinAmdinocillin may increase the anticoagulant activities of Acenocoumarol.Withdrawn
AmineptineAmineptine may increase the anticoagulant activities of Acenocoumarol.Illicit, Withdrawn
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Acenocoumarol.Approved
AmiodaroneAmiodarone may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AmitriptylineAmitriptyline may increase the anticoagulant activities of Acenocoumarol.Approved
AmobarbitalThe metabolism of Acenocoumarol can be increased when combined with Amobarbital.Approved, Illicit
AmorolfineAmorolfine may increase the anticoagulant activities of Acenocoumarol.Approved
AmoxicillinAmoxicillin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
AmpicillinAmpicillin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
AnagrelideAnagrelide may increase the anticoagulant activities of Acenocoumarol.Approved
AncrodAcenocoumarol may increase the anticoagulant activities of Ancrod.Investigational
AnisodamineAnisodamine may increase the anticoagulant activities of Acenocoumarol.Investigational
AnistreplaseAnistreplase may increase the anticoagulant activities of Acenocoumarol.Approved
AntipyrineAntipyrine may increase the anticoagulant activities of Acenocoumarol.Approved
Antithrombin III humanAcenocoumarol may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanApixaban may increase the anticoagulant activities of Acenocoumarol.Approved
ApremilastApremilast may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AprepitantThe serum concentration of Acenocoumarol can be increased when it is combined with Aprepitant.Approved, Investigational
AprotininThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Aprotinin.Approved, Withdrawn
ArdeparinArdeparin may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
ArgatrobanArgatroban may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
ArmodafinilThe metabolism of Acenocoumarol can be decreased when combined with Armodafinil.Approved, Investigational
AstaxanthinAstaxanthin may increase the anticoagulant activities of Acenocoumarol.Investigational
AtazanavirThe metabolism of Acenocoumarol can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Acenocoumarol can be decreased when combined with Atomoxetine.Approved
AtorvastatinAtorvastatin may increase the anticoagulant activities of Acenocoumarol.Approved
AzapropazoneAzapropazone may increase the anticoagulant activities of Acenocoumarol.Withdrawn
AzathioprineAzathioprine may decrease the anticoagulant activities of Acenocoumarol.Approved
AzelastineAzelastine may increase the anticoagulant activities of Acenocoumarol.Approved
AzidocillinAzidocillin may increase the anticoagulant activities of Acenocoumarol.Approved
AzithromycinThe metabolism of Acenocoumarol can be decreased when combined with Azithromycin.Approved
AzlocillinAzlocillin may increase the anticoagulant activities of Acenocoumarol.Approved
BacampicillinBacampicillin may increase the anticoagulant activities of Acenocoumarol.Approved
BalsalazideBalsalazide may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
BarbexacloneThe metabolism of Acenocoumarol can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Acenocoumarol can be increased when combined with Barbital.Illicit
BatroxobinBatroxobin may increase the anticoagulant activities of Acenocoumarol.Experimental
BazedoxifeneBazedoxifene may decrease the anticoagulant activities of Acenocoumarol.Approved, Investigational
BecaplerminBecaplermin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
BemiparinBemiparin may increase the anticoagulant activities of Acenocoumarol.Approved
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Acenocoumarol.Withdrawn
Benzathine benzylpenicillinBenzathine benzylpenicillin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
BenzylpenicillinBenzylpenicillin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
Benzylpenicillin PotassiumBenzylpenicillin Potassium may increase the anticoagulant activities of Acenocoumarol.Approved
Benzylpenicilloyl PolylysineBenzylpenicilloyl Polylysine may increase the anticoagulant activities of Acenocoumarol.Approved
BeraprostBeraprost may increase the anticoagulant activities of Acenocoumarol.Investigational
Betulinic AcidBetulinic Acid may increase the anticoagulant activities of Acenocoumarol.Investigational
BexaroteneThe serum concentration of Acenocoumarol can be decreased when it is combined with Bexarotene.Approved, Investigational
BezafibrateBezafibrate may increase the anticoagulant activities of Acenocoumarol.Approved
BicalutamideThe serum concentration of Acenocoumarol can be increased when it is combined with Bicalutamide.Approved
BivalirudinBivalirudin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
BoceprevirThe metabolism of Acenocoumarol can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Acenocoumarol can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe metabolism of Acenocoumarol can be increased when combined with Bosentan.Approved, Investigational
BromfenacBromfenac may increase the anticoagulant activities of Acenocoumarol.Approved
BucillamineBucillamine may increase the anticoagulant activities of Acenocoumarol.Investigational
ButylphthalideButylphthalide may increase the anticoagulant activities of Acenocoumarol.Investigational
CaffeineThe metabolism of Acenocoumarol can be decreased when combined with Caffeine.Approved
CangrelorCangrelor may increase the anticoagulant activities of Acenocoumarol.Approved
CapecitabineThe serum concentration of Acenocoumarol can be increased when it is combined with Capecitabine.Approved, Investigational
CarbamazepineThe serum concentration of Acenocoumarol can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarbenicillinCarbenicillin may increase the anticoagulant activities of Acenocoumarol.Approved
CarbimazoleCarbimazole may decrease the anticoagulant activities of Acenocoumarol.Approved
CarbomycinThe serum concentration of Acenocoumarol can be increased when it is combined with Carbomycin.Vet Approved
CarindacillinCarindacillin may increase the anticoagulant activities of Acenocoumarol.Approved
CarprofenCarprofen may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the anticoagulant activities of Acenocoumarol.Experimental
CefacetrileCefacetrile may increase the anticoagulant activities of Acenocoumarol.Approved
CefaclorCefaclor may increase the anticoagulant activities of Acenocoumarol.Approved
CefadroxilCefadroxil may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved, Withdrawn
CefalotinCefalotin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
CefamandoleCefamandole may increase the anticoagulant activities of Acenocoumarol.Approved
CefapirinCefapirin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
CefazolinCefazolin may increase the anticoagulant activities of Acenocoumarol.Approved
CefiximeCefixime may increase the anticoagulant activities of Acenocoumarol.Approved
CefmenoximeCefmenoxime may increase the anticoagulant activities of Acenocoumarol.Approved
CefmetazoleCefmetazole may increase the anticoagulant activities of Acenocoumarol.Approved
CefminoxCefminox may increase the anticoagulant activities of Acenocoumarol.Approved
CefonicidCefonicid may increase the anticoagulant activities of Acenocoumarol.Approved
CefoperazoneCefoperazone may increase the anticoagulant activities of Acenocoumarol.Approved
CeforanideCeforanide may increase the anticoagulant activities of Acenocoumarol.Approved
CefotaximeCefotaxime may increase the anticoagulant activities of Acenocoumarol.Approved
CefotetanCefotetan may increase the anticoagulant activities of Acenocoumarol.Approved
CefotiamCefotiam may increase the anticoagulant activities of Acenocoumarol.Approved
CefoxitinCefoxitin may increase the anticoagulant activities of Acenocoumarol.Approved
CefpodoximeCefpodoxime may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
CefradineCefradine may increase the anticoagulant activities of Acenocoumarol.Approved
CefroxadineCefroxadine may increase the anticoagulant activities of Acenocoumarol.Approved
CeftazidimeCeftazidime may increase the anticoagulant activities of Acenocoumarol.Approved
CeftizoximeCeftizoxime may increase the anticoagulant activities of Acenocoumarol.Approved
CeftriaxoneCeftriaxone may increase the anticoagulant activities of Acenocoumarol.Approved
CefuroximeCefuroxime may increase the anticoagulant activities of Acenocoumarol.Approved
CelecoxibCelecoxib may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
CephalexinCephalexin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
CephaloglycinCephaloglycin may increase the anticoagulant activities of Acenocoumarol.Approved
CephaloridineCephaloridine may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
CeritinibThe serum concentration of Acenocoumarol can be increased when it is combined with Ceritinib.Approved
CerivastatinCerivastatin may increase the anticoagulant activities of Acenocoumarol.Withdrawn
CertoparinAcenocoumarol may increase the anticoagulant activities of Certoparin.Approved
Chloral hydrateThe serum concentration of Acenocoumarol can be increased when it is combined with Chloral hydrate.Approved, Illicit, Vet Approved
ChloramphenicolChloramphenicol may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
ChloroquineChloroquine may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Acenocoumarol.Withdrawn
ChlorpropamideChlorpropamide may increase the anticoagulant activities of Acenocoumarol.Approved
ChlortetracyclineChlortetracycline may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
CholecalciferolThe metabolism of Acenocoumarol can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholestyramineCholestyramine can cause a decrease in the absorption of Acenocoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CilostazolCilostazol may increase the anticoagulant activities of Acenocoumarol.Approved
CimetidineCimetidine may increase the anticoagulant activities of Acenocoumarol.Approved
CinoxacinCinoxacin may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
CiprofibrateCiprofibrate may increase the anticoagulant activities of Acenocoumarol.Approved
CiprofloxacinCiprofloxacin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
CitalopramThe metabolism of Acenocoumarol can be decreased when combined with Citalopram.Approved
Citric AcidAcenocoumarol may increase the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Acenocoumarol can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Acenocoumarol can be decreased when combined with Clemastine.Approved
ClofibrateClofibrate may increase the anticoagulant activities of Acenocoumarol.Approved
ClomipramineClomipramine may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
ClonixinClonixin may increase the anticoagulant activities of Acenocoumarol.Approved
ClopidogrelClopidogrel may increase the anticoagulant activities of Acenocoumarol.Approved, Nutraceutical
ClotrimazoleThe metabolism of Acenocoumarol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CloxacillinCloxacillin may decrease the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
CobicistatThe metabolism of Acenocoumarol can be decreased when combined with Cobicistat.Approved
Coenzyme Q10Coenzyme Q10 may decrease the anticoagulant activities of Acenocoumarol.Experimental
ColesevelamColesevelam can cause a decrease in the absorption of Acenocoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Acenocoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CollagenaseThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Collagenase.Approved
ConivaptanThe serum concentration of Acenocoumarol can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated Equine EstrogensConjugated Equine Estrogens may decrease the anticoagulant activities of Acenocoumarol.Approved
CranberryCranberry may increase the anticoagulant activities of Acenocoumarol.Approved
CrizotinibThe metabolism of Acenocoumarol can be decreased when combined with Crizotinib.Approved
CurcuminCurcumin may increase the anticoagulant activities of Acenocoumarol.Investigational
CyclacillinCyclacillin may increase the anticoagulant activities of Acenocoumarol.Approved
CyclobenzaprineCyclobenzaprine may increase the anticoagulant activities of Acenocoumarol.Approved
CyclosporineThe metabolism of Acenocoumarol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Acenocoumarol can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
D-LimoneneD-Limonene may increase the anticoagulant activities of Acenocoumarol.Investigational
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Acenocoumarol.Approved
DabrafenibThe serum concentration of Acenocoumarol can be decreased when it is combined with Dabrafenib.Approved
DalteparinAcenocoumarol may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidAcenocoumarol may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DapoxetineDapoxetine may increase the anticoagulant activities of Acenocoumarol.Investigational
DarunavirThe metabolism of Acenocoumarol can be decreased when combined with Darunavir.Approved
DasatinibDasatinib may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
DeferasiroxThe serum concentration of Acenocoumarol can be decreased when it is combined with Deferasirox.Approved, Investigational
DefibrotideDefibrotide may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
DelavirdineThe metabolism of Acenocoumarol can be decreased when combined with Delavirdine.Approved
DemeclocyclineDemeclocycline may increase the anticoagulant activities of Acenocoumarol.Approved
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Deoxycholic Acid.Approved
dersalazinedersalazine may increase the anticoagulant activities of Acenocoumarol.Investigational
DesipramineDesipramine may increase the anticoagulant activities of Acenocoumarol.Approved
DesirudinAcenocoumarol may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Acenocoumarol.Investigational
DesogestrelDesogestrel may decrease the anticoagulant activities of Acenocoumarol.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Acenocoumarol.Approved
DexamethasoneThe serum concentration of Acenocoumarol can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexmethylphenidateThe serum concentration of Acenocoumarol can be increased when it is combined with Dexmethylphenidate.Approved
DextranAcenocoumarol may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Acenocoumarol may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Acenocoumarol may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Acenocoumarol may increase the anticoagulant activities of Dextran 75.Approved
DiclofenacDiclofenac may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
DicloxacillinDicloxacillin may decrease the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
DicoumarolDicoumarol may increase the anticoagulant activities of Acenocoumarol.Approved
DienestrolDienestrol may decrease the anticoagulant activities of Acenocoumarol.Approved
DienogestDienogest may decrease the anticoagulant activities of Acenocoumarol.Approved
DiethylstilbestrolDiethylstilbestrol may decrease the anticoagulant activities of Acenocoumarol.Approved
DiflunisalDiflunisal may increase the anticoagulant activities of Acenocoumarol.Approved
DihydroergotamineThe metabolism of Acenocoumarol can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneDihydrotestosterone may increase the anticoagulant activities of Acenocoumarol.Illicit
DiltiazemThe metabolism of Acenocoumarol can be decreased when combined with Diltiazem.Approved
DipyridamoleDipyridamole may increase the anticoagulant activities of Acenocoumarol.Approved
DisulfiramThe serum concentration of Acenocoumarol can be increased when it is combined with Disulfiram.Approved
DitazoleDitazole may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
DosulepinDosulepin may increase the anticoagulant activities of Acenocoumarol.Approved
DoxepinDoxepin may increase the anticoagulant activities of Acenocoumarol.Approved
DoxycyclineThe metabolism of Acenocoumarol can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Acenocoumarol can be increased when it is combined with Dronedarone.Approved
DrospirenoneDrospirenone may decrease the anticoagulant activities of Acenocoumarol.Approved
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational, Withdrawn
DroxicamDroxicam may increase the anticoagulant activities of Acenocoumarol.Approved
DuloxetineDuloxetine may increase the anticoagulant activities of Acenocoumarol.Approved
DuvelisibDuvelisib may increase the anticoagulant activities of Acenocoumarol.Investigational
DydrogesteroneThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Dydrogesterone.Approved, Withdrawn
E6201E6201 may increase the anticoagulant activities of Acenocoumarol.Investigational
EbselenEbselen may increase the anticoagulant activities of Acenocoumarol.Investigational
EconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Econazole.Approved
Edetic AcidEdetic Acid may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
EdoxabanEdoxaban may increase the anticoagulant activities of Acenocoumarol.Approved
EfavirenzThe serum concentration of Acenocoumarol can be decreased when it is combined with Efavirenz.Approved, Investigational
EnoxacinEnoxacin may increase the anticoagulant activities of Acenocoumarol.Approved
EnoxaparinEnoxaparin may increase the anticoagulant activities of Acenocoumarol.Approved
EnzalutamideThe serum concentration of Acenocoumarol can be decreased when it is combined with Enzalutamide.Approved
EpinastineEpinastine may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
EpirizoleEpirizole may increase the anticoagulant activities of Acenocoumarol.Approved
eplivanserineeplivanserine may increase the anticoagulant activities of Acenocoumarol.Investigational
EpoprostenolEpoprostenol may increase the anticoagulant activities of Acenocoumarol.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
ErythromycinThe metabolism of Acenocoumarol can be decreased when combined with Erythromycin.Approved, Vet Approved
ErythromycinThe serum concentration of Acenocoumarol can be increased when it is combined with Erythromycin.Approved, Vet Approved
EscitalopramEscitalopram may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Acenocoumarol can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsmirtazapineEsmirtazapine may increase the anticoagulant activities of Acenocoumarol.Investigational
EsomeprazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Esomeprazole.Approved, Investigational
EstradiolEstradiol may decrease the anticoagulant activities of Acenocoumarol.Approved, Investigational, Vet Approved
EstramustineEstramustine may decrease the anticoagulant activities of Acenocoumarol.Approved
EstriolEstriol may decrease the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
Estrogens, esterifiedEstrogens, esterified may decrease the anticoagulant activities of Acenocoumarol.Approved
EstroneEstrone may decrease the anticoagulant activities of Acenocoumarol.Approved
Estrone sulfateEstrone sulfate may decrease the anticoagulant activities of Acenocoumarol.Approved
Etacrynic acidThe serum concentration of Acenocoumarol can be increased when it is combined with Etacrynic acid.Approved
EtanerceptEtanercept may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
EthanolThe serum concentration of Acenocoumarol can be decreased when it is combined with Ethanol.Approved
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Acenocoumarol.Approved
EthotoinEthotoin may increase the anticoagulant activities of Acenocoumarol.Approved
Ethyl biscoumacetateAcenocoumarol may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Ethynodiol diacetateEthynodiol diacetate may decrease the anticoagulant activities of Acenocoumarol.Approved
EtodolacEtodolac may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the anticoagulant activities of Acenocoumarol.Approved
EtofibrateEtofibrate may increase the anticoagulant activities of Acenocoumarol.Approved
EtonogestrelEtonogestrel may decrease the anticoagulant activities of Acenocoumarol.Approved, Investigational
EtoperidoneEtoperidone may increase the anticoagulant activities of Acenocoumarol.Approved
EtoposideEtoposide may increase the anticoagulant activities of Acenocoumarol.Approved
EtoricoxibEtoricoxib may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
EtravirineThe serum concentration of Acenocoumarol can be decreased when it is combined with Etravirine.Approved
Evening primrose oilEvening primrose oil may increase the anticoagulant activities of Acenocoumarol.Approved
ExenatideExenatide may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
exisulindexisulind may increase the anticoagulant activities of Acenocoumarol.Investigational
FenbufenFenbufen may increase the anticoagulant activities of Acenocoumarol.Approved
FenofibrateFenofibrate may increase the anticoagulant activities of Acenocoumarol.Approved
FenoprofenFenoprofen may increase the anticoagulant activities of Acenocoumarol.Approved
FibrinolysinFibrinolysin may increase the anticoagulant activities of Acenocoumarol.Approved
FleroxacinFleroxacin may increase the anticoagulant activities of Acenocoumarol.Approved
FloctafenineFloctafenine may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
FloxuridineThe metabolism of Acenocoumarol can be decreased when combined with Floxuridine.Approved
FlucloxacillinFlucloxacillin may decrease the anticoagulant activities of Acenocoumarol.Approved
FluconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Fluconazole.Approved
FluindioneAcenocoumarol may increase the anticoagulant activities of Fluindione.Investigational
FlumequineFlumequine may increase the anticoagulant activities of Acenocoumarol.Withdrawn
FlunixinFlunixin may increase the anticoagulant activities of Acenocoumarol.Vet Approved
FluorouracilThe serum concentration of Acenocoumarol can be increased when it is combined with Fluorouracil.Approved
FluorouracilThe metabolism of Acenocoumarol can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Acenocoumarol can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluoxymesteroneFluoxymesterone may increase the anticoagulant activities of Acenocoumarol.Approved, Illicit
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
FluvastatinThe metabolism of Acenocoumarol can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Acenocoumarol can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxAcenocoumarol may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumFondaparinux sodium may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
FosamprenavirThe metabolism of Acenocoumarol can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Acenocoumarol can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinFosphenytoin may increase the anticoagulant activities of Acenocoumarol.Approved
Fusidic AcidThe serum concentration of Acenocoumarol can be increased when it is combined with Fusidic Acid.Approved
GabexateAcenocoumarol may increase the anticoagulant activities of Gabexate.Investigational
GarenoxacinGarenoxacin may increase the anticoagulant activities of Acenocoumarol.Investigational
GatifloxacinGatifloxacin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
GefitinibGefitinib may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
GemfibrozilThe metabolism of Acenocoumarol can be decreased when combined with Gemfibrozil.Approved
GemifloxacinGemifloxacin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
GenisteinGenistein may decrease the anticoagulant activities of Acenocoumarol.Investigational
GestodeneGestodene may decrease the anticoagulant activities of Acenocoumarol.Approved
GestrinoneThe therapeutic efficacy of Acenocoumarol 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 Acenocoumarol.Approved, Nutraceutical
GlibornurideGlibornuride may increase the anticoagulant activities of Acenocoumarol.Withdrawn
GliclazideGliclazide may increase the anticoagulant activities of Acenocoumarol.Approved
GlimepirideGlimepiride may increase the anticoagulant activities of Acenocoumarol.Approved
GlipizideGlipizide may increase the anticoagulant activities of Acenocoumarol.Approved
GliquidoneGliquidone may increase the anticoagulant activities of Acenocoumarol.Approved
GlisoxepideGlisoxepide may increase the anticoagulant activities of Acenocoumarol.Approved
Glucagon recombinantGlucagon recombinant may increase the anticoagulant activities of Acenocoumarol.Approved
GlutethimideThe metabolism of Acenocoumarol can be increased when combined with Glutethimide.Approved, Illicit
GlyburideGlyburide may increase the anticoagulant activities of Acenocoumarol.Approved
GrepafloxacinGrepafloxacin may increase the anticoagulant activities of Acenocoumarol.Withdrawn
GriseofulvinThe serum concentration of Acenocoumarol can be decreased when it is combined with Griseofulvin.Approved, Vet Approved
HeminHemin may increase the anticoagulant activities of Acenocoumarol.Approved
HeparinHeparin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
HexestrolHexestrol may decrease the anticoagulant activities of Acenocoumarol.Withdrawn
HexobarbitalThe metabolism of Acenocoumarol can be increased when combined with Hexobarbital.Approved
HigenamineHigenamine may increase the anticoagulant activities of Acenocoumarol.Investigational
HirulogAcenocoumarol may increase the anticoagulant activities of Hirulog.Experimental
HMPL-004HMPL-004 may increase the anticoagulant activities of Acenocoumarol.Investigational
Hydroxyprogesterone caproateThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Acenocoumarol.Approved
IbudilastIbudilast may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
IbuprofenIbuprofen may increase the anticoagulant activities of Acenocoumarol.Approved
IbuproxamIbuproxam may increase the anticoagulant activities of Acenocoumarol.Withdrawn
IcatibantIcatibant may increase the anticoagulant activities of Acenocoumarol.Approved
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Acenocoumarol.Approved, Nutraceutical
IdelalisibThe serum concentration of Acenocoumarol can be increased when it is combined with Idelalisib.Approved
idraparinuxAcenocoumarol may increase the anticoagulant activities of idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
IfosfamideIfosfamide may increase the anticoagulant activities of Acenocoumarol.Approved
IloprostIloprost may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
ImatinibThe metabolism of Acenocoumarol can be decreased when combined with Imatinib.Approved
ImipramineImipramine may increase the anticoagulant activities of Acenocoumarol.Approved
IndalpineIndalpine may increase the anticoagulant activities of Acenocoumarol.Investigational, Withdrawn
IndinavirThe metabolism of Acenocoumarol can be decreased when combined with Indinavir.Approved
IndobufenIndobufen may increase the anticoagulant activities of Acenocoumarol.Investigational
IndomethacinIndomethacin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
IndoprofenIndoprofen may increase the anticoagulant activities of Acenocoumarol.Withdrawn
IrbesartanThe metabolism of Acenocoumarol can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Acenocoumarol can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Acenocoumarol can be decreased when combined with Isoniazid.Approved
IsoxicamIsoxicam may increase the anticoagulant activities of Acenocoumarol.Withdrawn
IsradipineThe metabolism of Acenocoumarol can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Acenocoumarol can be increased when it is combined with Ivacaftor.Approved
IvermectinIvermectin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
JosamycinThe serum concentration of Acenocoumarol can be increased when it is combined with Josamycin.Approved
Kct 0809Kct 0809 may increase the anticoagulant activities of Acenocoumarol.Investigational
KebuzoneKebuzone may increase the anticoagulant activities of Acenocoumarol.Experimental
KetanserinKetanserin may increase the anticoagulant activities of Acenocoumarol.Investigational
KetoconazoleThe metabolism of Acenocoumarol can be decreased when combined with Ketoconazole.Approved, Investigational
KetoconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Ketoconazole.Approved, Investigational
KetoprofenKetoprofen may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
KetorolacKetorolac may increase the anticoagulant activities of Acenocoumarol.Approved
KitasamycinThe serum concentration of Acenocoumarol can be increased when it is combined with Kitasamycin.Experimental
L-CarnitineL-Carnitine may increase the anticoagulant activities of Acenocoumarol.Approved
LansoprazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Lansoprazole.Approved, Investigational
LeflunomideLeflunomide may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
LepirudinLepirudin may increase the anticoagulant activities of Acenocoumarol.Approved
LevofloxacinLevofloxacin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Acenocoumarol.Approved
LevonorgestrelLevonorgestrel may decrease the anticoagulant activities of Acenocoumarol.Approved, Investigational
LevothyroxineLevothyroxine may increase the anticoagulant activities of Acenocoumarol.Approved
LidocaineThe metabolism of Acenocoumarol can be decreased when combined with Lidocaine.Approved, Vet Approved
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Acenocoumarol.Approved
LiothyronineLiothyronine may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
LiotrixLiotrix may increase the anticoagulant activities of Acenocoumarol.Approved
LisofyllineLisofylline may increase the anticoagulant activities of Acenocoumarol.Investigational
LixisenatideLixisenatide can cause a decrease in the absorption of Acenocoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
LomefloxacinLomefloxacin may increase the anticoagulant activities of Acenocoumarol.Approved
LopinavirThe metabolism of Acenocoumarol can be decreased when combined with Lopinavir.Approved
LornoxicamLornoxicam may increase the anticoagulant activities of Acenocoumarol.Approved
LosartanThe metabolism of Acenocoumarol can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Acenocoumarol can be decreased when combined with Lovastatin.Approved, Investigational
LoxoprofenLoxoprofen may increase the anticoagulant activities of Acenocoumarol.Approved
LuliconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Acenocoumarol can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
LynestrenolLynestrenol may decrease the anticoagulant activities of Acenocoumarol.Investigational
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Acenocoumarol.Approved
MasoprocolMasoprocol may increase the anticoagulant activities of Acenocoumarol.Approved
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
MedrogestoneThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Medrogestone.Approved
Medroxyprogesterone acetateMedroxyprogesterone acetate may decrease the anticoagulant activities of Acenocoumarol.Approved, Investigational
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Acenocoumarol.Approved
Megestrol acetateThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Megestrol acetate.Approved, Vet Approved
MeloxicamMeloxicam may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
MercaptopurineMercaptopurine may decrease the anticoagulant activities of Acenocoumarol.Approved
MesalazineMesalazine may increase the anticoagulant activities of Acenocoumarol.Approved
MestranolMestranol may decrease the anticoagulant activities of Acenocoumarol.Approved
MetamizoleMetamizole may increase the anticoagulant activities of Acenocoumarol.Withdrawn
MethallenestrilMethallenestril may decrease the anticoagulant activities of Acenocoumarol.Experimental
MethimazoleMethimazole may decrease the anticoagulant activities of Acenocoumarol.Approved
MethohexitalThe metabolism of Acenocoumarol can be increased when combined with Methohexital.Approved
MethylphenidateThe serum concentration of Acenocoumarol can be increased when it is combined with Methylphenidate.Approved, Investigational
MethylphenobarbitalThe metabolism of Acenocoumarol can be increased when combined with Methylphenobarbital.Approved
MethyltestosteroneMethyltestosterone may increase the anticoagulant activities of Acenocoumarol.Approved
MeticillinMeticillin may increase the anticoagulant activities of Acenocoumarol.Approved
MetronidazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Metronidazole.Approved
MevastatinMevastatin may increase the anticoagulant activities of Acenocoumarol.Experimental
MexiletineThe metabolism of Acenocoumarol can be decreased when combined with Mexiletine.Approved
MezlocillinMezlocillin may increase the anticoagulant activities of Acenocoumarol.Approved
MiconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MifepristoneThe serum concentration of Acenocoumarol 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 Acenocoumarol.Approved
MilrinoneMilrinone may increase the anticoagulant activities of Acenocoumarol.Approved
MinocyclineMinocycline may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
MirtazapineMirtazapine may increase the anticoagulant activities of Acenocoumarol.Approved
MitotaneThe serum concentration of Acenocoumarol can be decreased when it is combined with Mitotane.Approved
MizoribineMizoribine may increase the anticoagulant activities of Acenocoumarol.Investigational
MoclobemideThe metabolism of Acenocoumarol can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Acenocoumarol can be decreased when it is combined with Modafinil.Approved, Investigational
MoxifloxacinMoxifloxacin may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Acenocoumarol.Approved
NabumetoneNabumetone may increase the anticoagulant activities of Acenocoumarol.Approved
NadroparinAcenocoumarol may increase the anticoagulant activities of Nadroparin.Approved
NafamostatNafamostat may increase the anticoagulant activities of Acenocoumarol.Investigational
NafcillinNafcillin may decrease the anticoagulant activities of Acenocoumarol.Approved
NaftifineNaftifine may increase the anticoagulant activities of Acenocoumarol.Approved
NaftopidilNaftopidil may increase the anticoagulant activities of Acenocoumarol.Investigational
Nalidixic AcidNalidixic Acid may increase the anticoagulant activities of Acenocoumarol.Approved
NaproxenNaproxen may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
NCX 4016NCX 4016 may increase the anticoagulant activities of Acenocoumarol.Investigational
NefazodoneThe metabolism of Acenocoumarol can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Acenocoumarol can be decreased when combined with Nelfinavir.Approved
NemonoxacinNemonoxacin may increase the anticoagulant activities of Acenocoumarol.Investigational
NeomycinNeomycin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
NepafenacNepafenac may increase the anticoagulant activities of Acenocoumarol.Approved
NetupitantThe serum concentration of Acenocoumarol can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Acenocoumarol can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Acenocoumarol can be decreased when combined with Nicardipine.Approved
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Acenocoumarol.Approved
NilotinibThe metabolism of Acenocoumarol can be decreased when combined with Nilotinib.Approved, Investigational
NimesulideNimesulide may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
NintedanibThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Nintedanib.Approved
NitroaspirinNitroaspirin may increase the anticoagulant activities of Acenocoumarol.Investigational
NomegestrolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Nomegestrol.Approved
NorelgestrominNorelgestromin may decrease the anticoagulant activities of Acenocoumarol.Approved
NorethisteroneThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Norethisterone.Approved
NorfloxacinNorfloxacin may increase the anticoagulant activities of Acenocoumarol.Approved
NorgestimateNorgestimate may decrease the anticoagulant activities of Acenocoumarol.Approved
NorgestrelNorgestrel may decrease the anticoagulant activities of Acenocoumarol.Approved
NortriptylineNortriptyline may increase the anticoagulant activities of Acenocoumarol.Approved
ObinutuzumabThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Obinutuzumab.Approved
OfloxacinOfloxacin may increase the anticoagulant activities of Acenocoumarol.Approved
OlaparibThe metabolism of Acenocoumarol can be decreased when combined with Olaparib.Approved
OleandomycinThe serum concentration of Acenocoumarol can be increased when it is combined with Oleandomycin.Vet Approved
OlopatadineOlopatadine may increase the anticoagulant activities of Acenocoumarol.Approved
OlsalazineOlsalazine may increase the anticoagulant activities of Acenocoumarol.Approved
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Omacetaxine mepesuccinate.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Acenocoumarol.Approved
OmeprazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OpipramolOpipramol may increase the anticoagulant activities of Acenocoumarol.Investigational
OrgoteinOrgotein may increase the anticoagulant activities of Acenocoumarol.Vet Approved
OritavancinThe serum concentration of Acenocoumarol can be increased when it is combined with Oritavancin.Approved, Investigational
OsimertinibThe serum concentration of Acenocoumarol can be increased when it is combined with Osimertinib.Approved
OtamixabanAcenocoumarol may increase the anticoagulant activities of Otamixaban.Investigational
OxacillinOxacillin may increase the anticoagulant activities of Acenocoumarol.Approved
OxandroloneOxandrolone may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
OxaprozinOxaprozin may increase the anticoagulant activities of Acenocoumarol.Approved
OxymetholoneOxymetholone may increase the anticoagulant activities of Acenocoumarol.Approved, Illicit
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Acenocoumarol.Withdrawn
OxytetracyclineOxytetracycline may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
PalbociclibThe serum concentration of Acenocoumarol can be increased when it is combined with Palbociclib.Approved
PantoprazoleThe metabolism of Acenocoumarol can be decreased when combined with Pantoprazole.Approved
ParecoxibParecoxib may increase the anticoagulant activities of Acenocoumarol.Approved
ParnaparinParnaparin may increase the anticoagulant activities of Acenocoumarol.Approved
ParoxetineParoxetine may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
PazufloxacinPazufloxacin may increase the anticoagulant activities of Acenocoumarol.Investigational
PefloxacinPefloxacin may increase the anticoagulant activities of Acenocoumarol.Approved
Peginterferon alfa-2bThe serum concentration of Acenocoumarol can be increased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Acenocoumarol can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Acenocoumarol.Approved
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
PhenindionePhenindione may increase the anticoagulant activities of Acenocoumarol.Approved
PhenobarbitalThe metabolism of Acenocoumarol can be increased when combined with Phenobarbital.Approved
PhenoxymethylpenicillinPhenoxymethylpenicillin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
PhenprocoumonPhenprocoumon may increase the anticoagulant activities of Acenocoumarol.Approved
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
PhenytoinPhenytoin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
PhylloquinonePhylloquinone may decrease the anticoagulant activities of Acenocoumarol.Approved
PimecrolimusPimecrolimus may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
PiperacillinPiperacillin may increase the anticoagulant activities of Acenocoumarol.Approved
PirfenidonePirfenidone may increase the anticoagulant activities of Acenocoumarol.Investigational
PiroxicamPiroxicam may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
PitavastatinPitavastatin may increase the anticoagulant activities of Acenocoumarol.Approved
PivampicillinPivampicillin may increase the anticoagulant activities of Acenocoumarol.Approved
PivmecillinamPivmecillinam may increase the anticoagulant activities of Acenocoumarol.Approved
PlasminPlasmin may increase the anticoagulant activities of Acenocoumarol.Investigational
Polyestradiol phosphatePolyestradiol phosphate may decrease the anticoagulant activities of Acenocoumarol.Approved
PosaconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrasugrelPrasugrel may increase the anticoagulant activities of Acenocoumarol.Approved
PravastatinPravastatin may increase the anticoagulant activities of Acenocoumarol.Approved
PrimidoneThe metabolism of Acenocoumarol can be increased when combined with Primidone.Approved, Vet Approved
Procaine benzylpenicillinProcaine benzylpenicillin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
ProgesteroneThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Progesterone.Approved, Vet Approved
PromestrienePromestriene may decrease the anticoagulant activities of Acenocoumarol.Investigational
PropacetamolPropacetamol may increase the anticoagulant activities of Acenocoumarol.Approved
PropafenoneThe serum concentration of Acenocoumarol can be increased when it is combined with Propafenone.Approved
PropylthiouracilPropylthiouracil may decrease the anticoagulant activities of Acenocoumarol.Approved
Protein CAcenocoumarol may increase the anticoagulant activities of Protein C.Approved
Protein S humanAcenocoumarol may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeAcenocoumarol may increase the anticoagulant activities of Protocatechualdehyde.Approved
ProtriptylineProtriptyline may increase the anticoagulant activities of Acenocoumarol.Approved
PrulifloxacinPrulifloxacin may increase the anticoagulant activities of Acenocoumarol.Investigational
PTC299PTC299 may increase the anticoagulant activities of Acenocoumarol.Investigational
PyrimethamineThe metabolism of Acenocoumarol can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinestrolQuinestrol may decrease the anticoagulant activities of Acenocoumarol.Approved
QuinidineQuinidine may increase the anticoagulant activities of Acenocoumarol.Approved
QuinineQuinine may increase the anticoagulant activities of Acenocoumarol.Approved
RamatrobanRamatroban may increase the anticoagulant activities of Acenocoumarol.Investigational
RanolazineThe metabolism of Acenocoumarol can be decreased when combined with Ranolazine.Approved, Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Acenocoumarol.Experimental, Investigational
ReteplaseReteplase may increase the anticoagulant activities of Acenocoumarol.Approved
ReviparinAcenocoumarol may increase the anticoagulant activities of Reviparin.Approved
RidogrelRidogrel may increase the anticoagulant activities of Acenocoumarol.Approved
RifabutinThe metabolism of Acenocoumarol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Acenocoumarol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Acenocoumarol can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Acenocoumarol can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanAcenocoumarol may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the anticoagulant activities of Acenocoumarol.Investigational, Withdrawn
RopiniroleThe metabolism of Acenocoumarol can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneRosiglitazone may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
RosoxacinRosoxacin may increase the anticoagulant activities of Acenocoumarol.Approved
RosuvastatinRosuvastatin may increase the anticoagulant activities of Acenocoumarol.Approved
S EquolS Equol may decrease the anticoagulant activities of Acenocoumarol.Investigational
SalicylamideSalicylamide may increase the anticoagulant activities of Acenocoumarol.Approved
Salicylic acidSalicylic acid may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
SalsalateSalsalate may increase the anticoagulant activities of Acenocoumarol.Approved
SaquinavirThe metabolism of Acenocoumarol can be decreased when combined with Saquinavir.Approved, Investigational
SCH-530348SCH-530348 may increase the anticoagulant activities of Acenocoumarol.Investigational
SecobarbitalThe metabolism of Acenocoumarol can be increased when combined with Secobarbital.Approved, Vet Approved
SecoisolariciresinolSecoisolariciresinol may decrease the anticoagulant activities of Acenocoumarol.Investigational
SelexipagSelexipag may increase the anticoagulant activities of Acenocoumarol.Approved
SeratrodastSeratrodast may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
SertralineThe metabolism of Acenocoumarol can be decreased when combined with Sertraline.Approved
SevofluraneSevoflurane may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
SildenafilThe metabolism of Acenocoumarol can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Acenocoumarol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Acenocoumarol can be increased when it is combined with Simeprevir.Approved
SimvastatinSimvastatin may increase the anticoagulant activities of Acenocoumarol.Approved
SolithromycinThe serum concentration of Acenocoumarol can be increased when it is combined with Solithromycin.Investigational
SorafenibThe metabolism of Acenocoumarol can be decreased when combined with Sorafenib.Approved, Investigational
SparfloxacinSparfloxacin may increase the anticoagulant activities of Acenocoumarol.Approved
SRT501SRT501 may increase the anticoagulant activities of Acenocoumarol.Investigational
St. John's WortThe metabolism of Acenocoumarol can be increased when combined with St. John&#39;s Wort.Nutraceutical
StanozololStanozolol may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
StiripentolThe serum concentration of Acenocoumarol can be increased when it is combined with Stiripentol.Approved
StreptokinaseStreptokinase may increase the anticoagulant activities of Acenocoumarol.Approved
SucralfateSucralfate may decrease the anticoagulant activities of Acenocoumarol.Approved
SugammadexSugammadex may increase the anticoagulant activities of Acenocoumarol.Approved
SulbactamSulbactam may increase the anticoagulant activities of Acenocoumarol.Approved
SulfadiazineThe metabolism of Acenocoumarol can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleSulfamethoxazole may increase the anticoagulant activities of Acenocoumarol.Approved
SulfasalazineSulfasalazine may increase the anticoagulant activities of Acenocoumarol.Approved
SulfinpyrazoneThe metabolism of Acenocoumarol can be decreased when combined with Sulfinpyrazone.Approved
SulfisoxazoleThe metabolism of Acenocoumarol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulindacSulindac may increase the anticoagulant activities of Acenocoumarol.Approved
SulodexideAcenocoumarol may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SultamicillinSultamicillin may increase the anticoagulant activities of Acenocoumarol.Investigational
SuprofenSuprofen may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Acenocoumarol.Approved
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Acenocoumarol.Approved
TamoxifenThe serum concentration of Acenocoumarol can be increased when it is combined with Tamoxifen.Approved
TazobactamTazobactam may increase the anticoagulant activities of Acenocoumarol.Approved
TegafurThe serum concentration of Acenocoumarol can be increased when it is combined with Tegafur.Approved
TelaprevirThe metabolism of Acenocoumarol can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Acenocoumarol can be decreased when combined with Telithromycin.Approved
TemafloxacinTemafloxacin may increase the anticoagulant activities of Acenocoumarol.Withdrawn
TenecteplaseTenecteplase may increase the anticoagulant activities of Acenocoumarol.Approved
TenofovirThe metabolism of Acenocoumarol can be decreased when combined with Tenofovir.Approved, Investigational
TenoxicamTenoxicam may increase the anticoagulant activities of Acenocoumarol.Approved
TepoxalinTepoxalin may increase the anticoagulant activities of Acenocoumarol.Vet Approved
TeriflunomideThe serum concentration of Acenocoumarol can be decreased when it is combined with Teriflunomide.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Acenocoumarol.Investigational
TestosteroneTestosterone may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
TetracyclineTetracycline may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
TheophyllineThe metabolism of Acenocoumarol can be decreased when combined with Theophylline.Approved
ThiamylalThe metabolism of Acenocoumarol can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Acenocoumarol can be increased when combined with Thiopental.Approved, Vet Approved
Thyroid, porcineThyroid, porcine may increase the anticoagulant activities of Acenocoumarol.Approved
TianeptineTianeptine may increase the anticoagulant activities of Acenocoumarol.Approved
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Acenocoumarol.Approved
TiboloneTibolone may increase the anticoagulant activities of Acenocoumarol.Approved
TicagrelorThe metabolism of Acenocoumarol can be decreased when combined with Ticagrelor.Approved
TicarcillinTicarcillin may increase the anticoagulant activities of Acenocoumarol.Approved, Vet Approved
TiclopidineThe metabolism of Acenocoumarol can be decreased when combined with Ticlopidine.Approved
TinoridineTinoridine may increase the anticoagulant activities of Acenocoumarol.Investigational
TinzaparinTinzaparin may increase the anticoagulant activities of Acenocoumarol.Approved
TipranavirTipranavir may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Acenocoumarol.Approved
TocilizumabThe serum concentration of Acenocoumarol can be decreased when it is combined with Tocilizumab.Approved
TolazamideTolazamide may increase the anticoagulant activities of Acenocoumarol.Approved
TolbutamideThe metabolism of Acenocoumarol can be decreased when combined with Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Acenocoumarol.Approved
TolmetinTolmetin may increase the anticoagulant activities of Acenocoumarol.Approved
TopiramateThe metabolism of Acenocoumarol can be decreased when combined with Topiramate.Approved
ToremifeneToremifene may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
TositumomabThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Tositumomab.Approved
TramadolTramadol may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
TranilastTranilast may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
TranylcypromineThe metabolism of Acenocoumarol can be decreased when combined with Tranylcypromine.Approved
TrapidilTrapidil may increase the anticoagulant activities of Acenocoumarol.Approved
TreprostinilTreprostinil may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
TriflusalTriflusal may increase the anticoagulant activities of Acenocoumarol.Approved
TrimethoprimThe metabolism of Acenocoumarol can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineTrimipramine may increase the anticoagulant activities of Acenocoumarol.Approved
Trisalicylate-cholineTrisalicylate-choline may increase the anticoagulant activities of Acenocoumarol.Approved
TroleandomycinThe serum concentration of Acenocoumarol can be increased when it is combined with Troleandomycin.Approved
TrovafloxacinTrovafloxacin may increase the anticoagulant activities of Acenocoumarol.Approved, Withdrawn
TylosinThe serum concentration of Acenocoumarol can be increased when it is combined with Tylosin.Vet Approved
UrokinaseUrokinase may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational, Withdrawn
ValdecoxibValdecoxib may increase the anticoagulant activities of Acenocoumarol.Investigational, Withdrawn
Valproic AcidThe metabolism of Acenocoumarol can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Acenocoumarol can be decreased when combined with Valsartan.Approved, Investigational
VemurafenibThe serum concentration of Acenocoumarol can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Acenocoumarol.Approved
VerapamilThe metabolism of Acenocoumarol can be decreased when combined with Verapamil.Approved
Vitamin EVitamin E may increase the anticoagulant activities of Acenocoumarol.Approved, Nutraceutical, Vet Approved
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Acenocoumarol.Approved
VoriconazoleThe serum concentration of Acenocoumarol can be increased when it is combined with Voriconazole.Approved, Investigational
VorinostatVorinostat may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
WarfarinWarfarin may increase the anticoagulant activities of Acenocoumarol.Approved
XimelagatranAcenocoumarol may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Ym150Acenocoumarol may increase the anticoagulant activities of Ym150.Investigational
ZafirlukastThe serum concentration of Acenocoumarol can be increased when it is combined with Zafirlukast.Approved, Investigational
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Acenocoumarol.Approved
ZeranolZeranol may decrease the anticoagulant activities of Acenocoumarol.Vet Approved
ZileutonZileuton may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational, Withdrawn
ZimelidineZimelidine may increase the anticoagulant activities of Acenocoumarol.Withdrawn
ZiprasidoneThe metabolism of Acenocoumarol can be decreased when combined with Ziprasidone.Approved
ZomepiracZomepirac may increase the anticoagulant activities of Acenocoumarol.Withdrawn
Food Interactions
  • High doses of vitamin A, C, E and K (e.g. avocado, green vegetables)
References
Synthesis Reference

Stoll, W. and Litvan, F.; U.S. Patent 2,648,682; August 11,1953; assigned to J.R. Geigy A.G.,
Switzerland.

General References
  1. Cesar JM, Garcia-Avello A, Navarro JL, Herraez MV: Aging and oral anticoagulant therapy using acenocoumarol. Blood Coagul Fibrinolysis. 2004 Oct;15(8):673-6. [PubMed:15613922 ]
  2. Lengyel M: [Warfarin or acenocoumarol is better in the anticoagulant treatment of chronic atrial fibrillation?]. Orv Hetil. 2004 Dec 26;145(52):2619-21. [PubMed:15724697 ]
  3. Ufer M: Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46. [PubMed:16372822 ]
  4. Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. [PubMed:16611310 ]
  5. Girard P, Nony P, Erhardtsen E, Delair S, Ffrench P, Dechavanne M, Boissel JP: Population pharmacokinetics of recombinant factor VIIa in volunteers anticoagulated with acenocoumarol. Thromb Haemost. 1998 Jul;80(1):109-13. [PubMed:9684795 ]
External Links
ATC CodesB01AA07
AHFS Codes
  • 20:12.04.08
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (126 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7518
Blood Brain Barrier+0.5765
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.6031
P-glycoprotein inhibitor INon-inhibitor0.7078
P-glycoprotein inhibitor IINon-inhibitor0.843
Renal organic cation transporterNon-inhibitor0.8944
CYP450 2C9 substrateNon-substrate0.6256
CYP450 2D6 substrateNon-substrate0.8936
CYP450 3A4 substrateSubstrate0.6267
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7492
Ames testAMES toxic0.6954
CarcinogenicityNon-carcinogens0.7015
BiodegradationNot ready biodegradable0.9403
Rat acute toxicity2.7869 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6326
hERG inhibition (predictor II)Non-inhibitor0.9347
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral1 mg
TabletOral4 mg
Prices
Unit descriptionCostUnit
Sintrom 4 mg Tablet1.6USD tablet
Sintrom 1 mg Tablet0.51USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point196-199Merck Index 23
water solubilitypractically insolubleMSDS
logP1.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0106 mg/mLALOGPS
logP2.53ALOGPS
logP2.68ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)5.79ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.42 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.18 m3·mol-1ChemAxon
Polarizability34.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • 1-benzopyran
  • Benzopyran
  • Nitrobenzene
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Lactone
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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. 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. Bodin L, Verstuyft C, Tregouet DA, Robert A, Dubert L, Funck-Brentano C, Jaillon P, Beaune P, Laurent-Puig P, Becquemont L, Loriot MA: Cytochrome P450 2C9 (CYP2C9) and vitamin K epoxide reductase (VKORC1) genotypes as determinants of acenocoumarol sensitivity. Blood. 2005 Jul 1;106(1):135-40. Epub 2005 Mar 24. [PubMed:15790782 ]
  3. Gonzalez-Conejero R, Corral J, Roldan V, Ferrer F, Sanchez-Serrano I, Sanchez-Blanco JJ, Marin F, Vicente V: The genetic interaction between VKORC1 c1173t and calumenin a29809g modulates the anticoagulant response of acenocoumarol. J Thromb Haemost. 2007 Aug;5(8):1701-6. Epub 2007 May 21. [PubMed:17596133 ]
  4. Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. [PubMed:16611310 ]
  5. Rettie AE, Farin FM, Beri NG, Srinouanprachanh SL, Rieder MJ, Thijssen HH: A case study of acenocoumarol sensitivity and genotype-phenotype discordancy explained by combinations of polymorphisms in VKORC1 and CYP2C9. Br J Clin Pharmacol. 2006 Nov;62(5):617-20. Epub 2006 Jul 21. [PubMed:16869821 ]
  6. Schalekamp T, Brasse BP, Roijers JF, Chahid Y, van Geest-Daalderop JH, de Vries-Goldschmeding H, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and acenocoumarol anticoagulation status: interaction between both genotypes affects overanticoagulation. Clin Pharmacol Ther. 2006 Jul;80(1):13-22. [PubMed:16815313 ]
  7. 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
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. 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. Stehle S, Kirchheiner J, Lazar A, Fuhr U: Pharmacogenetics of oral anticoagulants: a basis for dose individualization. Clin Pharmacokinet. 2008;47(9):565-94. [PubMed:18698879 ]
  3. Bodin L, Verstuyft C, Tregouet DA, Robert A, Dubert L, Funck-Brentano C, Jaillon P, Beaune P, Laurent-Puig P, Becquemont L, Loriot MA: Cytochrome P450 2C9 (CYP2C9) and vitamin K epoxide reductase (VKORC1) genotypes as determinants of acenocoumarol sensitivity. Blood. 2005 Jul 1;106(1):135-40. Epub 2005 Mar 24. [PubMed:15790782 ]
  4. Gonzalez-Conejero R, Corral J, Roldan V, Ferrer F, Sanchez-Serrano I, Sanchez-Blanco JJ, Marin F, Vicente V: The genetic interaction between VKORC1 c1173t and calumenin a29809g modulates the anticoagulant response of acenocoumarol. J Thromb Haemost. 2007 Aug;5(8):1701-6. Epub 2007 May 21. [PubMed:17596133 ]
  5. Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. [PubMed:16611310 ]
  6. Rettie AE, Farin FM, Beri NG, Srinouanprachanh SL, Rieder MJ, Thijssen HH: A case study of acenocoumarol sensitivity and genotype-phenotype discordancy explained by combinations of polymorphisms in VKORC1 and CYP2C9. Br J Clin Pharmacol. 2006 Nov;62(5):617-20. Epub 2006 Jul 21. [PubMed:16869821 ]
  7. Schalekamp T, Brasse BP, Roijers JF, Chahid Y, van Geest-Daalderop JH, de Vries-Goldschmeding H, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and acenocoumarol anticoagulation status: interaction between both genotypes affects overanticoagulation. Clin Pharmacol Ther. 2006 Jul;80(1):13-22. [PubMed:16815313 ]
  8. 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:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 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 ]
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. Ufer M: Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46. [PubMed:16372822 ]
  2. Morales-Molina JA, Arrebola MA, Robles PA, Mangana JC: Possible interaction between topical terbinafine and acenocoumarol. Ann Pharmacother. 2009 Nov;43(11):1911-2. doi: 10.1345/aph.1M299. Epub 2009 Oct 20. [PubMed:19843835 ]

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. Fitos I, Visy J, Simonyi M, Hermansson J: Stereoselective distribution of acenocoumarol enantiomers in human plasma: chiral chromatographic analysis of the ultrafiltrates. Chirality. 1993;5(5):346-9. [PubMed:8398591 ]
  2. Fitos I, Visy J, Magyar A, Kajtar J, Simonyi M: Inverse stereoselectivity in the binding of acenocoumarol to human serum albumin and to alpha 1-acid glycoprotein. Biochem Pharmacol. 1989 Jul 15;38(14):2259-62. [PubMed:2751692 ]
  3. Otagiri M, Fleitman JS, Perrin JH: Investigations into the binding of phenprocoumon to albumin using fluorescence spectroscopy. J Pharm Pharmacol. 1980 Jul;32(7):478-82. [PubMed:6105183 ]
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. Fitos I, Visy J, Simonyi M, Hermansson J: Stereoselective distribution of acenocoumarol enantiomers in human plasma: chiral chromatographic analysis of the ultrafiltrates. Chirality. 1993;5(5):346-9. [PubMed:8398591 ]
  2. Fitos I, Visy J, Magyar A, Kajtar J, Simonyi M: Inverse stereoselectivity in the binding of acenocoumarol to human serum albumin and to alpha 1-acid glycoprotein. Biochem Pharmacol. 1989 Jul 15;38(14):2259-62. [PubMed:2751692 ]
  3. 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 July 24, 2007 02:32 / Updated on August 17, 2016 12:23