Phenindione - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)

Targets (1)Biointeractions (1)

Identification

Name

Phenindione

Accession Number

DB00498 (APRD00166)

Type

Small Molecule

Groups

Approved

Description

An indandione that has been used as an anticoagulant. Phenindione has actions similar to warfarin, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

2-Phenyl-1,3-diketohydrindene

2-Phenyl-1,3-indandione

2-Phenyl-1,3(2H)-indenedione

Fenindiona

Fenindione

Phenindion

Phénindione

Phenindionum

PID

External IDs

Not Available

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Dindevan	Sigma
Fenindion	Souriree
Phenindione	Goldshield
Soluthrombine	Cooper

Brand mixtures

Not Available

Categories

UNII

5M7Y6274ZE

CAS number

83-12-5

Weight

Average: 222.2387
Monoisotopic: 222.068079564

Chemical Formula

C₁₅H₁₀O₂

InChI Key

NFBAXHOPROOJAW-UHFFFAOYSA-N

InChI

InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H

IUPAC Name

2-phenyl-2,3-dihydro-1H-indene-1,3-dione

SMILES

O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, mural thrombosis, and thrombophili. Also used for anticoagulant prophylaxis.

Structured Indications

Not Available

Pharmacodynamics

Phenindione thins the blood by antagonizing vitamin K which is required for the production of clotting factors in the liver. Anticoagulants such as Phenindione 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. Phenindione has actions similar to warfarin, but it is now rarely employed because of its higer incidence of severe adverse effects.

Mechanism of action

Phenindione 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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Vitamin K epoxide reductase complex subunit 1	Protein	yes	inhibitor	Human	Q9BQB6	details

Absorption

Absorbed slowly from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

88%

Metabolism

Hepatic.

Route of elimination

Not Available

Half life

5-10 hours

Clearance

Not Available

Toxicity

Oral, mouse: LD50 = 175 mg/kg; Oral, rat: LD50 = 163 mg/kg.

Affected organisms

Humans and other mammals

Pathways

Pathway	Category	SMPDB ID
Phenindione Action Pathway	Drug action	SMP00655

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Abciximab	Abciximab may increase the anticoagulant activities of Phenindione.	Approved
Aceclofenac	Aceclofenac may increase the anticoagulant activities of Phenindione.	Approved
Acenocoumarol	Phenindione may increase the anticoagulant activities of Acenocoumarol.	Approved
Acetaminophen	Acetaminophen may increase the anticoagulant activities of Phenindione.	Approved
Acetohexamide	Acetohexamide may increase the anticoagulant activities of Phenindione.	Withdrawn
Acetylsalicylic acid	Acetylsalicylic acid may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Adapalene	Adapalene may increase the anticoagulant activities of Phenindione.	Approved
Allopurinol	Allopurinol may increase the anticoagulant activities of Phenindione.	Approved
Allylestrenol	The therapeutic efficacy of Phenindione can be decreased when used in combination with Allylestrenol.	Approved
Alprostadil	Alprostadil may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Alteplase	Alteplase may increase the anticoagulant activities of Phenindione.	Approved
Amdinocillin	Amdinocillin may increase the anticoagulant activities of Phenindione.	Withdrawn
Amineptine	Amineptine may increase the anticoagulant activities of Phenindione.	Illicit, Withdrawn
Aminosalicylic Acid	Aminosalicylic Acid may increase the anticoagulant activities of Phenindione.	Approved
Amiodarone	Amiodarone may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Amitriptyline	Amitriptyline may increase the anticoagulant activities of Phenindione.	Approved
Amobarbital	The metabolism of Phenindione can be increased when combined with Amobarbital.	Approved, Illicit
Amoxicillin	Amoxicillin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Ampicillin	Ampicillin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Anagrelide	Anagrelide may increase the anticoagulant activities of Phenindione.	Approved
Ancrod	Phenindione may increase the anticoagulant activities of Ancrod.	Investigational
Andrographolide	HMPL-004 may increase the anticoagulant activities of Phenindione.	Investigational
Anisodamine	Anisodamine may increase the anticoagulant activities of Phenindione.	Investigational
Anistreplase	Anistreplase may increase the anticoagulant activities of Phenindione.	Approved
Antipyrine	Antipyrine may increase the anticoagulant activities of Phenindione.	Approved
Antithrombin III human	Phenindione may increase the anticoagulant activities of Antithrombin III human.	Approved
Apixaban	Apixaban may increase the anticoagulant activities of Phenindione.	Approved
Apocynin	Acetovanillone may increase the anticoagulant activities of Phenindione.	Investigational
Apremilast	Apremilast may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Aprotinin	The therapeutic efficacy of Phenindione can be decreased when used in combination with Aprotinin.	Approved, Withdrawn
Ardeparin	Ardeparin may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Argatroban	Argatroban may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Atorvastatin	Atorvastatin may increase the anticoagulant activities of Phenindione.	Approved
Azapropazone	Azapropazone may increase the anticoagulant activities of Phenindione.	Withdrawn
Azathioprine	Azathioprine may decrease the anticoagulant activities of Phenindione.	Approved
Azelastine	Azelastine may increase the anticoagulant activities of Phenindione.	Approved
Azidocillin	Azidocillin may increase the anticoagulant activities of Phenindione.	Approved
Azithromycin	The serum concentration of Phenindione can be increased when it is combined with Azithromycin.	Approved
Azlocillin	Azlocillin may increase the anticoagulant activities of Phenindione.	Approved
Bacampicillin	Bacampicillin may increase the anticoagulant activities of Phenindione.	Approved
Balsalazide	Balsalazide may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Barbexaclone	The metabolism of Phenindione can be increased when combined with Barbexaclone.	Experimental
Barbital	The metabolism of Phenindione can be increased when combined with Barbital.	Illicit
Bazedoxifene	Bazedoxifene may decrease the anticoagulant activities of Phenindione.	Approved, Investigational
Becaplermin	Becaplermin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Bemiparin	Bemiparin may increase the anticoagulant activities of Phenindione.	Approved
Benoxaprofen	Benoxaprofen may increase the anticoagulant activities of Phenindione.	Withdrawn
Benzathine benzylpenicillin	Benzathine benzylpenicillin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Benzylpenicillin	Benzylpenicillin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Benzylpenicilloyl Polylysine	Benzylpenicilloyl Polylysine may increase the anticoagulant activities of Phenindione.	Approved
Beraprost	Beraprost may increase the anticoagulant activities of Phenindione.	Investigational
Betulinic Acid	Betulinic Acid may increase the anticoagulant activities of Phenindione.	Investigational
Bezafibrate	Bezafibrate may increase the anticoagulant activities of Phenindione.	Approved
Bicalutamide	The serum concentration of Phenindione can be increased when it is combined with Bicalutamide.	Approved
Bivalirudin	Bivalirudin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Bosentan	The metabolism of Phenindione can be increased when combined with Bosentan.	Approved, Investigational
Bromfenac	Bromfenac may increase the anticoagulant activities of Phenindione.	Approved
Bucillamine	Bucillamine may increase the anticoagulant activities of Phenindione.	Investigational
Butylphthalide	Butylphthalide may increase the anticoagulant activities of Phenindione.	Investigational
Cangrelor	Cangrelor may increase the anticoagulant activities of Phenindione.	Approved
Capecitabine	The serum concentration of Phenindione can be increased when it is combined with Capecitabine.	Approved, Investigational
Carbamazepine	The serum concentration of Phenindione can be decreased when it is combined with Carbamazepine.	Approved, Investigational
Carbenicillin	Carbenicillin may increase the anticoagulant activities of Phenindione.	Approved
Carbimazole	Carbimazole may decrease the anticoagulant activities of Phenindione.	Approved
Carprofen	Carprofen may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved, Withdrawn
Castanospermine	Castanospermine may increase the anticoagulant activities of Phenindione.	Experimental
Cefacetrile	Cefacetrile may increase the anticoagulant activities of Phenindione.	Approved
Cefaclor	Cefaclor may increase the anticoagulant activities of Phenindione.	Approved
Cefadroxil	Cefadroxil may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved, Withdrawn
Cefalotin	Cefalotin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Cefamandole	Cefamandole may increase the anticoagulant activities of Phenindione.	Approved
Cefapirin	Cefapirin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Cefazolin	Cefazolin may increase the anticoagulant activities of Phenindione.	Approved
Cefixime	Cefixime may increase the anticoagulant activities of Phenindione.	Approved
Cefmenoxime	Cefmenoxime may increase the anticoagulant activities of Phenindione.	Approved
Cefmetazole	Cefmetazole may increase the anticoagulant activities of Phenindione.	Approved
Cefonicid	Cefonicid may increase the anticoagulant activities of Phenindione.	Approved
Cefoperazone	Cefoperazone may increase the anticoagulant activities of Phenindione.	Approved
Ceforanide	Ceforanide may increase the anticoagulant activities of Phenindione.	Approved
Cefotaxime	Cefotaxime may increase the anticoagulant activities of Phenindione.	Approved
Cefotetan	Cefotetan may increase the anticoagulant activities of Phenindione.	Approved
Cefotiam	Cefotiam may increase the anticoagulant activities of Phenindione.	Approved
Cefoxitin	Cefoxitin may increase the anticoagulant activities of Phenindione.	Approved
Cefpodoxime	Cefpodoxime may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Cefradine	Cefradine may increase the anticoagulant activities of Phenindione.	Approved
Cefroxadine	Cefroxadine may increase the anticoagulant activities of Phenindione.	Withdrawn
Ceftazidime	Ceftazidime may increase the anticoagulant activities of Phenindione.	Approved
Ceftizoxime	Ceftizoxime may increase the anticoagulant activities of Phenindione.	Approved
Ceftriaxone	Ceftriaxone may increase the anticoagulant activities of Phenindione.	Approved
Cefuroxime	Cefuroxime may increase the anticoagulant activities of Phenindione.	Approved
Celecoxib	Celecoxib may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Cephalexin	Cephalexin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Cephaloglycin	Cephaloglycin may increase the anticoagulant activities of Phenindione.	Approved
Cephaloridine	Cephaloridine may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Cerivastatin	Cerivastatin may increase the anticoagulant activities of Phenindione.	Withdrawn
Certoparin	Phenindione may increase the anticoagulant activities of Certoparin.	Approved
Chloral hydrate	The serum concentration of Phenindione can be increased when it is combined with Chloral hydrate.	Approved, Illicit, Vet Approved
Chloramphenicol	Chloramphenicol may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Chloroquine	Chloroquine may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Chlorotrianisene	Chlorotrianisene may decrease the anticoagulant activities of Phenindione.	Withdrawn
Chlorpropamide	Chlorpropamide may increase the anticoagulant activities of Phenindione.	Approved
Chlortetracycline	Chlortetracycline may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Cholestyramine	Cholestyramine can cause a decrease in the absorption of Phenindione resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Choline magnesium trisalicylate	Trisalicylate-choline may increase the anticoagulant activities of Phenindione.	Approved
Cilostazol	Cilostazol may increase the anticoagulant activities of Phenindione.	Approved
Cimetidine	Cimetidine may increase the anticoagulant activities of Phenindione.	Approved
Cinoxacin	Cinoxacin may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Ciprofloxacin	Ciprofloxacin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Citalopram	Citalopram may increase the anticoagulant activities of Phenindione.	Approved
Citric Acid	Phenindione may increase the anticoagulant activities of Citric Acid.	Nutraceutical, Vet Approved
Clarithromycin	The serum concentration of Phenindione can be increased when it is combined with Clarithromycin.	Approved
Clofibrate	Clofibrate may increase the anticoagulant activities of Phenindione.	Approved
Clomipramine	Clomipramine may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Clonixin	Clonixin may increase the anticoagulant activities of Phenindione.	Approved
Clopidogrel	Clopidogrel may increase the anticoagulant activities of Phenindione.	Approved, Nutraceutical
Cloxacillin	Cloxacillin may decrease the anticoagulant activities of Phenindione.	Approved, Vet Approved
Colesevelam	Colesevelam can cause a decrease in the absorption of Phenindione resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Colestipol	Colestipol can cause a decrease in the absorption of Phenindione resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Conjugated estrogens	Conjugated Equine Estrogens may decrease the anticoagulant activities of Phenindione.	Approved
Curcumin	Curcumin may increase the anticoagulant activities of Phenindione.	Investigational
Cyclacillin	Cyclacillin may increase the anticoagulant activities of Phenindione.	Approved
Cyclobenzaprine	Cyclobenzaprine may increase the anticoagulant activities of Phenindione.	Approved
Dabigatran etexilate	Dabigatran etexilate may increase the anticoagulant activities of Phenindione.	Approved
Dalteparin	Phenindione may increase the anticoagulant activities of Dalteparin.	Approved
Dapoxetine	Dapoxetine may increase the anticoagulant activities of Phenindione.	Investigational
Darexaban	Phenindione may increase the anticoagulant activities of Ym150.	Investigational
Dasatinib	Dasatinib may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Deferasirox	The risk or severity of adverse effects can be increased when Phenindione is combined with Deferasirox.	Approved, Investigational
Defibrotide	Defibrotide may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Demeclocycline	Demeclocycline may increase the anticoagulant activities of Phenindione.	Approved
Deoxycholic Acid	The risk or severity of adverse effects can be increased when Phenindione is combined with Deoxycholic Acid.	Approved
Desipramine	Desipramine may increase the anticoagulant activities of Phenindione.	Approved
Desirudin	Phenindione may increase the anticoagulant activities of Desirudin.	Approved
Desmoteplase	Desmoteplase may increase the anticoagulant activities of Phenindione.	Investigational
Desogestrel	Desogestrel may decrease the anticoagulant activities of Phenindione.	Approved
Desvenlafaxine	The risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Phenindione.	Approved
Dexmethylphenidate	The serum concentration of Phenindione can be increased when it is combined with Dexmethylphenidate.	Approved
Dextran	Phenindione may increase the anticoagulant activities of Dextran.	Approved, Vet Approved
Dextran 40	Phenindione may increase the anticoagulant activities of Dextran 40.	Approved
Diclofenac	Diclofenac may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Dicloxacillin	Dicloxacillin may decrease the anticoagulant activities of Phenindione.	Approved, Vet Approved
Dicoumarol	Dicoumarol may increase the anticoagulant activities of Phenindione.	Approved
Dienestrol	Dienestrol may decrease the anticoagulant activities of Phenindione.	Approved
Dienogest	Dienogest may decrease the anticoagulant activities of Phenindione.	Approved
Diethylstilbestrol	Diethylstilbestrol may decrease the anticoagulant activities of Phenindione.	Approved
Diflunisal	Diflunisal may increase the anticoagulant activities of Phenindione.	Approved
Dihydrotestosterone	Dihydrotestosterone may increase the anticoagulant activities of Phenindione.	Illicit
Dipyridamole	Dipyridamole may increase the anticoagulant activities of Phenindione.	Approved
Disulfiram	The serum concentration of Phenindione can be increased when it is combined with Disulfiram.	Approved
Ditazole	Ditazole may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Dosulepin	Dosulepin may increase the anticoagulant activities of Phenindione.	Approved
Doxepin	Doxepin may increase the anticoagulant activities of Phenindione.	Approved
Doxycycline	Doxycycline may increase the anticoagulant activities of Phenindione.	Approved, Investigational, Vet Approved
Dronedarone	The serum concentration of Phenindione can be increased when it is combined with Dronedarone.	Approved
Drospirenone	Drospirenone may decrease the anticoagulant activities of Phenindione.	Approved
Drotrecogin alfa	Drotrecogin alfa may increase the anticoagulant activities of Phenindione.	Approved, Investigational, Withdrawn
Droxicam	Droxicam may increase the anticoagulant activities of Phenindione.	Approved
Duloxetine	Duloxetine may increase the anticoagulant activities of Phenindione.	Approved
Duvelisib	Duvelisib may increase the anticoagulant activities of Phenindione.	Investigational
Dydrogesterone	The therapeutic efficacy of Phenindione can be decreased when used in combination with Dydrogesterone.	Approved, Withdrawn
E-6201	E6201 may increase the anticoagulant activities of Phenindione.	Investigational
Ebselen	Ebselen may increase the anticoagulant activities of Phenindione.	Investigational
Econazole	The serum concentration of Phenindione can be increased when it is combined with Econazole.	Approved
Edetic Acid	Phenindione may increase the anticoagulant activities of Edetic Acid.	Approved, Vet Approved
Edoxaban	Edoxaban may increase the anticoagulant activities of Phenindione.	Approved
Efavirenz	The serum concentration of Phenindione can be decreased when it is combined with Efavirenz.	Approved, Investigational
Enoxacin	Enoxacin may increase the anticoagulant activities of Phenindione.	Approved
Enoxaparin	Phenindione may increase the anticoagulant activities of Enoxaparin.	Approved
Epinastine	Epinastine may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Epirizole	Epirizole may increase the anticoagulant activities of Phenindione.	Approved
Epoprostenol	Epoprostenol may increase the anticoagulant activities of Phenindione.	Approved
Eptifibatide	Eptifibatide may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Equol	S Equol may decrease the anticoagulant activities of Phenindione.	Investigational
Erythromycin	The serum concentration of Phenindione can be increased when it is combined with Erythromycin.	Approved, Vet Approved
Escitalopram	Escitalopram may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Esmirtazapine	Esmirtazapine may increase the anticoagulant activities of Phenindione.	Investigational
Esomeprazole	The serum concentration of Phenindione can be increased when it is combined with Esomeprazole.	Approved, Investigational
Estradiol	Estradiol may decrease the anticoagulant activities of Phenindione.	Approved, Investigational, Vet Approved
Estramustine	Estramustine may decrease the anticoagulant activities of Phenindione.	Approved
Estriol	Estriol may decrease the anticoagulant activities of Phenindione.	Approved, Vet Approved
Estrogens, esterified	Estrogens, esterified may decrease the anticoagulant activities of Phenindione.	Approved
Estrone	Estrone may decrease the anticoagulant activities of Phenindione.	Approved
Estrone sulfate	Estrone sulfate may decrease the anticoagulant activities of Phenindione.	Approved
Etacrynic acid	The serum concentration of Phenindione can be increased when it is combined with Etacrynic acid.	Approved
Etanercept	Etanercept may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Ethanol	The serum concentration of Phenindione can be decreased when it is combined with Ethanol.	Approved
Ethinyl Estradiol	Ethinyl Estradiol may decrease the anticoagulant activities of Phenindione.	Approved
Ethotoin	Ethotoin may increase the anticoagulant activities of Phenindione.	Approved
Ethyl biscoumacetate	Phenindione may increase the anticoagulant activities of Ethyl biscoumacetate.	Withdrawn
Ethynodiol diacetate	Ethynodiol diacetate may decrease the anticoagulant activities of Phenindione.	Approved
Etodolac	Etodolac may increase the anticoagulant activities of Phenindione.	Approved, Investigational, Vet Approved
Etofenamate	Etofenamate may increase the anticoagulant activities of Phenindione.	Approved
Etofibrate	Etofibrate may increase the anticoagulant activities of Phenindione.	Approved
Etonogestrel	Etonogestrel may decrease the anticoagulant activities of Phenindione.	Approved, Investigational
Etoperidone	Etoperidone may increase the anticoagulant activities of Phenindione.	Approved
Etoposide	Etoposide may increase the anticoagulant activities of Phenindione.	Approved
Etoricoxib	Etoricoxib may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Exenatide	Exenatide may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Fenbufen	Fenbufen may increase the anticoagulant activities of Phenindione.	Approved
Fenofibrate	Fenofibrate may increase the anticoagulant activities of Phenindione.	Approved
Fenoprofen	Fenoprofen may increase the anticoagulant activities of Phenindione.	Approved
Fibrinolysin	Plasmin may increase the anticoagulant activities of Phenindione.	Investigational
Fleroxacin	Fleroxacin may increase the anticoagulant activities of Phenindione.	Approved
Floctafenine	Floctafenine may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Flucloxacillin	Flucloxacillin may decrease the anticoagulant activities of Phenindione.	Approved
Fluconazole	The serum concentration of Phenindione can be increased when it is combined with Fluconazole.	Approved
Fluindione	Phenindione may increase the anticoagulant activities of Fluindione.	Investigational
Flumequine	Flumequine may increase the anticoagulant activities of Phenindione.	Withdrawn
Fluorouracil	The serum concentration of Phenindione can be increased when it is combined with Fluorouracil.	Approved
Fluoxetine	Fluoxetine may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Fluoxymesterone	Fluoxymesterone may increase the anticoagulant activities of Phenindione.	Approved, Illicit
Flurbiprofen	Flurbiprofen may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Fluvastatin	Fluvastatin may increase the anticoagulant activities of Phenindione.	Approved
Fluvoxamine	Fluvoxamine may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Fondaparinux	Phenindione may increase the anticoagulant activities of Fondaparinux.	Investigational
Fondaparinux sodium	Phenindione may increase the anticoagulant activities of Fondaparinux sodium.	Approved, Investigational
Fosphenytoin	Fosphenytoin may increase the anticoagulant activities of Phenindione.	Approved
Fusidic Acid	The serum concentration of Phenindione can be increased when it is combined with Fusidic Acid.	Approved
Gabexate	Phenindione may increase the anticoagulant activities of Gabexate.	Investigational
Gatifloxacin	Gatifloxacin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Gefitinib	Gefitinib may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Gemfibrozil	Gemfibrozil may increase the anticoagulant activities of Phenindione.	Approved
Gemifloxacin	Gemifloxacin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Genistein	Genistein may decrease the anticoagulant activities of Phenindione.	Investigational
Gestodene	Gestodene may decrease the anticoagulant activities of Phenindione.	Approved
Gestrinone	The therapeutic efficacy of Phenindione can be decreased when used in combination with Gestrinone.	Approved
Ginkgo biloba	The risk or severity of adverse effects can be increased when Ginkgo biloba is combined with Phenindione.	Approved, Nutraceutical
Glibornuride	Glibornuride may increase the anticoagulant activities of Phenindione.	Withdrawn
Gliclazide	Gliclazide may increase the anticoagulant activities of Phenindione.	Approved
Glimepiride	Glimepiride may increase the anticoagulant activities of Phenindione.	Approved
Glipizide	Glipizide may increase the anticoagulant activities of Phenindione.	Approved
Gliquidone	Gliquidone may increase the anticoagulant activities of Phenindione.	Approved
Glisoxepide	Glisoxepide may increase the anticoagulant activities of Phenindione.	Approved
Glucagon recombinant	Glucagon recombinant may increase the anticoagulant activities of Phenindione.	Approved
Glutethimide	The metabolism of Phenindione can be increased when combined with Glutethimide.	Approved, Illicit
Glyburide	Glyburide may increase the anticoagulant activities of Phenindione.	Approved
Grepafloxacin	Grepafloxacin may increase the anticoagulant activities of Phenindione.	Withdrawn
Griseofulvin	The serum concentration of Phenindione can be decreased when it is combined with Griseofulvin.	Approved, Vet Approved
Hemin	Hemin may increase the anticoagulant activities of Phenindione.	Approved
Heparin	Phenindione may increase the anticoagulant activities of Heparin.	Approved, Investigational
Hexestrol	Hexestrol may decrease the anticoagulant activities of Phenindione.	Withdrawn
Hexobarbital	The metabolism of Phenindione can be increased when combined with Hexobarbital.	Approved
Higenamine	Higenamine may increase the anticoagulant activities of Phenindione.	Investigational
Hydroxyprogesterone caproate	The therapeutic efficacy of Phenindione can be decreased when used in combination with Hydroxyprogesterone caproate.	Approved
Ibritumomab tiuxetan	The risk or severity of adverse effects can be increased when Phenindione is combined with Ibritumomab tiuxetan.	Approved
Ibrutinib	The risk or severity of adverse effects can be increased when Ibrutinib is combined with Phenindione.	Approved
Ibudilast	Ibudilast may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Ibuprofen	Ibuprofen may increase the anticoagulant activities of Phenindione.	Approved
Ibuproxam	Ibuproxam may increase the anticoagulant activities of Phenindione.	Withdrawn
Icatibant	Icatibant may increase the anticoagulant activities of Phenindione.	Approved
Icosapent ethyl	Icosapent ethyl may increase the anticoagulant activities of Phenindione.	Approved, Nutraceutical
Ifenprodil	Ifenprodil may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Ifosfamide	Ifosfamide may increase the anticoagulant activities of Phenindione.	Approved
Iloprost	Iloprost may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Imipramine	Imipramine may increase the anticoagulant activities of Phenindione.	Approved
Indalpine	Indalpine may increase the anticoagulant activities of Phenindione.	Investigational, Withdrawn
Indobufen	Indobufen may increase the anticoagulant activities of Phenindione.	Investigational
Indomethacin	Indomethacin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Indoprofen	Indoprofen may increase the anticoagulant activities of Phenindione.	Withdrawn
Isoxicam	Isoxicam may increase the anticoagulant activities of Phenindione.	Withdrawn
Itraconazole	The serum concentration of Phenindione can be increased when it is combined with Itraconazole.	Approved, Investigational
Ivermectin	Ivermectin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Josamycin	The serum concentration of Phenindione can be increased when it is combined with Josamycin.	Approved
Kebuzone	Kebuzone may increase the anticoagulant activities of Phenindione.	Experimental
Ketanserin	Ketanserin may increase the anticoagulant activities of Phenindione.	Investigational
Ketoconazole	The serum concentration of Phenindione can be increased when it is combined with Ketoconazole.	Approved, Investigational
Ketoprofen	Ketoprofen may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Ketorolac	Ketorolac may increase the anticoagulant activities of Phenindione.	Approved
Kitasamycin	The serum concentration of Phenindione can be increased when it is combined with Kitasamycin.	Experimental
L-Carnitine	L-Carnitine may increase the anticoagulant activities of Phenindione.	Approved
Lansoprazole	The serum concentration of Phenindione can be increased when it is combined with Lansoprazole.	Approved, Investigational
Leflunomide	Leflunomide may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Lepirudin	Lepirudin may increase the anticoagulant activities of Phenindione.	Approved
Levofloxacin	Levofloxacin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Levomilnacipran	The risk or severity of adverse effects can be increased when Levomilnacipran is combined with Phenindione.	Approved
Levonorgestrel	Levonorgestrel may decrease the anticoagulant activities of Phenindione.	Approved, Investigational
Levothyroxine	Levothyroxine may increase the anticoagulant activities of Phenindione.	Approved
Limaprost	The risk or severity of adverse effects can be increased when Limaprost is combined with Phenindione.	Approved
Liothyronine	Liothyronine may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Liotrix	Liotrix may increase the anticoagulant activities of Phenindione.	Approved
Lisofylline	Lisofylline may increase the anticoagulant activities of Phenindione.	Investigational
Lixisenatide	Lixisenatide can cause a decrease in the absorption of Phenindione resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Lomefloxacin	Lomefloxacin may increase the anticoagulant activities of Phenindione.	Approved
Lornoxicam	Lornoxicam may increase the anticoagulant activities of Phenindione.	Approved
Lovastatin	Lovastatin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Loxoprofen	Loxoprofen may increase the anticoagulant activities of Phenindione.	Approved
Lumiracoxib	Lumiracoxib may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Lynestrenol	Lynestrenol may decrease the anticoagulant activities of Phenindione.	Investigational
Magnesium salicylate	Magnesium salicylate may increase the anticoagulant activities of Phenindione.	Approved
Masoprocol	Masoprocol may increase the anticoagulant activities of Phenindione.	Approved
Meclofenamic acid	Meclofenamic acid may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Medrogestone	The therapeutic efficacy of Phenindione can be decreased when used in combination with Medrogestone.	Approved
Medroxyprogesterone acetate	Medroxyprogesterone acetate may decrease the anticoagulant activities of Phenindione.	Approved, Investigational
Mefenamic acid	Mefenamic acid may increase the anticoagulant activities of Phenindione.	Approved
Megestrol acetate	The therapeutic efficacy of Phenindione can be decreased when used in combination with Megestrol acetate.	Approved, Vet Approved
Meloxicam	Meloxicam may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Mercaptopurine	Mercaptopurine may decrease the anticoagulant activities of Phenindione.	Approved
Mesalazine	Mesalazine may increase the anticoagulant activities of Phenindione.	Approved
Mestranol	Mestranol may decrease the anticoagulant activities of Phenindione.	Approved
Metamizole	Metamizole may increase the anticoagulant activities of Phenindione.	Withdrawn
Methallenestril	Methallenestril may decrease the anticoagulant activities of Phenindione.	Experimental
Methimazole	Methimazole may decrease the anticoagulant activities of Phenindione.	Approved
Methohexital	The metabolism of Phenindione can be increased when combined with Methohexital.	Approved
Methylphenidate	The serum concentration of Phenindione can be increased when it is combined with Methylphenidate.	Approved, Investigational
Methylphenobarbital	The metabolism of Phenindione can be increased when combined with Methylphenobarbital.	Approved
Methyltestosterone	Methyltestosterone may increase the anticoagulant activities of Phenindione.	Approved
Meticillin	Meticillin may increase the anticoagulant activities of Phenindione.	Approved
Metronidazole	The serum concentration of Phenindione can be increased when it is combined with Metronidazole.	Approved
Mevastatin	Mevastatin may increase the anticoagulant activities of Phenindione.	Experimental
Mezlocillin	Mezlocillin may increase the anticoagulant activities of Phenindione.	Approved
Miconazole	The serum concentration of Phenindione can be increased when it is combined with Miconazole.	Approved, Investigational, Vet Approved
Milnacipran	The risk or severity of adverse effects can be increased when Milnacipran is combined with Phenindione.	Approved
Milrinone	Milrinone may increase the anticoagulant activities of Phenindione.	Approved
Minocycline	Minocycline may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Mirtazapine	Mirtazapine may increase the anticoagulant activities of Phenindione.	Approved
Mizoribine	Mizoribine may increase the anticoagulant activities of Phenindione.	Investigational
Moxifloxacin	Moxifloxacin may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Mycophenolate mofetil	Mycophenolate mofetil may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Mycophenolic acid	Mycophenolic acid may increase the anticoagulant activities of Phenindione.	Approved
Nabumetone	Nabumetone may increase the anticoagulant activities of Phenindione.	Approved
Nadroparin	Phenindione may increase the anticoagulant activities of Nadroparin.	Approved
Nafamostat	Nafamostat may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Nafcillin	Nafcillin may decrease the anticoagulant activities of Phenindione.	Approved
Naftifine	Naftifine may increase the anticoagulant activities of Phenindione.	Approved
Naftopidil	Naftopidil may increase the anticoagulant activities of Phenindione.	Investigational
Nalidixic Acid	Nalidixic Acid may increase the anticoagulant activities of Phenindione.	Approved
Naproxen	Naproxen may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Nefazodone	Nefazodone may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Neomycin	Neomycin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Nepafenac	Nepafenac may increase the anticoagulant activities of Phenindione.	Approved
Niflumic Acid	Niflumic Acid may increase the anticoagulant activities of Phenindione.	Approved
Nimesulide	Nimesulide may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Nintedanib	The risk or severity of adverse effects can be increased when Phenindione is combined with Nintedanib.	Approved
Nitroaspirin	Nitroaspirin may increase the anticoagulant activities of Phenindione.	Investigational
Norelgestromin	Norelgestromin may decrease the anticoagulant activities of Phenindione.	Approved
Norethisterone	The therapeutic efficacy of Phenindione can be decreased when used in combination with Norethisterone.	Approved
Norfloxacin	Norfloxacin may increase the anticoagulant activities of Phenindione.	Approved
Norgestimate	Norgestimate may decrease the anticoagulant activities of Phenindione.	Approved
Norgestrel	Norgestrel may decrease the anticoagulant activities of Phenindione.	Approved
Nortriptyline	Nortriptyline may increase the anticoagulant activities of Phenindione.	Approved
Obinutuzumab	The risk or severity of adverse effects can be increased when Phenindione is combined with Obinutuzumab.	Approved
Ofloxacin	Ofloxacin may increase the anticoagulant activities of Phenindione.	Approved
Olopatadine	Olopatadine may increase the anticoagulant activities of Phenindione.	Approved
Olsalazine	Olsalazine may increase the anticoagulant activities of Phenindione.	Approved
Omacetaxine mepesuccinate	The risk or severity of adverse effects can be increased when Phenindione is combined with Omacetaxine mepesuccinate.	Approved
Omega-3 fatty acids	Omega-3 fatty acids may increase the anticoagulant activities of Phenindione.	Approved, Nutraceutical
Omeprazole	The serum concentration of Phenindione can be increased when it is combined with Omeprazole.	Approved, Investigational, Vet Approved
Opipramol	Opipramol may increase the anticoagulant activities of Phenindione.	Investigational
Oritavancin	The serum concentration of Phenindione can be increased when it is combined with Oritavancin.	Approved, Investigational
Oxacillin	Oxacillin may increase the anticoagulant activities of Phenindione.	Approved
Oxandrolone	Oxandrolone may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Oxaprozin	Oxaprozin may increase the anticoagulant activities of Phenindione.	Approved
Oxymetholone	Oxymetholone may increase the anticoagulant activities of Phenindione.	Approved, Illicit
Oxyphenbutazone	Oxyphenbutazone may increase the anticoagulant activities of Phenindione.	Withdrawn
Oxytetracycline	Oxytetracycline may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Ozagrel	Kct 0809 may increase the anticoagulant activities of Phenindione.	Investigational
Parecoxib	Parecoxib may increase the anticoagulant activities of Phenindione.	Approved
Parnaparin	Parnaparin may increase the anticoagulant activities of Phenindione.	Approved
Paroxetine	Paroxetine may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Pazufloxacin	Pazufloxacin may increase the anticoagulant activities of Phenindione.	Investigational
Pefloxacin	Pefloxacin may increase the anticoagulant activities of Phenindione.	Approved
Pentobarbital	The metabolism of Phenindione can be increased when combined with Pentobarbital.	Approved, Vet Approved
Pentosan Polysulfate	Pentosan Polysulfate may increase the anticoagulant activities of Phenindione.	Approved
Pentoxifylline	Pentoxifylline may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Phenobarbital	The metabolism of Phenindione can be increased when combined with Phenobarbital.	Approved
Phenoxymethylpenicillin	Phenoxymethylpenicillin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Phenprocoumon	Phenindione may increase the anticoagulant activities of Phenprocoumon.	Approved
Phenylbutazone	Phenylbutazone may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Phenytoin	Phenytoin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Phylloquinone	Phylloquinone may decrease the anticoagulant activities of Phenindione.	Approved
Pimecrolimus	Pimecrolimus may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Piperacillin	Piperacillin may increase the anticoagulant activities of Phenindione.	Approved
Pirfenidone	Pirfenidone may increase the anticoagulant activities of Phenindione.	Investigational
Piroxicam	Piroxicam may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Pitavastatin	Pitavastatin may increase the anticoagulant activities of Phenindione.	Approved
Pivampicillin	Pivampicillin may increase the anticoagulant activities of Phenindione.	Approved
Pivmecillinam	Pivmecillinam may increase the anticoagulant activities of Phenindione.	Approved
Posaconazole	The serum concentration of Phenindione can be increased when it is combined with Posaconazole.	Approved, Investigational, Vet Approved
Prasugrel	Prasugrel may increase the anticoagulant activities of Phenindione.	Approved
Pravastatin	Pravastatin may increase the anticoagulant activities of Phenindione.	Approved
Primidone	The metabolism of Phenindione can be increased when combined with Primidone.	Approved, Vet Approved
Procaine benzylpenicillin	Procaine benzylpenicillin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Progesterone	The therapeutic efficacy of Phenindione can be decreased when used in combination with Progesterone.	Approved, Vet Approved
Promestriene	Promestriene may decrease the anticoagulant activities of Phenindione.	Investigational
Propacetamol	Propacetamol may increase the anticoagulant activities of Phenindione.	Approved
Propafenone	The serum concentration of Phenindione can be increased when it is combined with Propafenone.	Approved
Propylthiouracil	Propylthiouracil may decrease the anticoagulant activities of Phenindione.	Approved
Protein S human	Phenindione may increase the anticoagulant activities of Protein S human.	Approved
Protriptyline	Protriptyline may increase the anticoagulant activities of Phenindione.	Approved
Prulifloxacin	Prulifloxacin may increase the anticoagulant activities of Phenindione.	Investigational
PTC299	PTC299 may increase the anticoagulant activities of Phenindione.	Investigational
Quinestrol	Quinestrol may decrease the anticoagulant activities of Phenindione.	Approved
Quinidine	Quinidine may increase the anticoagulant activities of Phenindione.	Approved
Quinine	Quinine may increase the anticoagulant activities of Phenindione.	Approved
Ramatroban	Ramatroban may increase the anticoagulant activities of Phenindione.	Investigational
Resveratrol	Resveratrol may increase the anticoagulant activities of Phenindione.	Experimental, Investigational
Reteplase	Reteplase may increase the anticoagulant activities of Phenindione.	Approved
Reviparin	Phenindione may increase the anticoagulant activities of Reviparin.	Approved
Ridogrel	Ridogrel may increase the anticoagulant activities of Phenindione.	Approved
Rifabutin	The metabolism of Phenindione can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Phenindione can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Phenindione can be increased when combined with Rifapentine.	Approved
Rivaroxaban	Phenindione may increase the anticoagulant activities of Rivaroxaban.	Approved
Rofecoxib	Rofecoxib may increase the anticoagulant activities of Phenindione.	Investigational, Withdrawn
Rosiglitazone	Rosiglitazone may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Rosoxacin	Rosoxacin may increase the anticoagulant activities of Phenindione.	Approved
Rosuvastatin	Rosuvastatin may increase the anticoagulant activities of Phenindione.	Approved
Salicylamide	Salicylamide may increase the anticoagulant activities of Phenindione.	Approved
Salicylic acid	Salicylic acid may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Salsalate	Salsalate may increase the anticoagulant activities of Phenindione.	Approved
Secobarbital	The metabolism of Phenindione can be increased when combined with Secobarbital.	Approved, Vet Approved
Secoisolariciresinol	Secoisolariciresinol may decrease the anticoagulant activities of Phenindione.	Investigational
Selexipag	Selexipag may increase the anticoagulant activities of Phenindione.	Approved
Sertraline	Sertraline may increase the anticoagulant activities of Phenindione.	Approved
Sevoflurane	Sevoflurane may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Simvastatin	Simvastatin may increase the anticoagulant activities of Phenindione.	Approved
Solithromycin	The serum concentration of Phenindione can be increased when it is combined with Solithromycin.	Investigational
Sparfloxacin	Sparfloxacin may increase the anticoagulant activities of Phenindione.	Approved
SRT501	SRT501 may increase the anticoagulant activities of Phenindione.	Investigational
St. John's Wort	The metabolism of Phenindione can be increased when combined with St. John's Wort.	Nutraceutical
Stanozolol	Stanozolol may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Streptokinase	Streptokinase may increase the anticoagulant activities of Phenindione.	Approved
Sucralfate	Sucralfate may decrease the anticoagulant activities of Phenindione.	Approved
Sugammadex	Sugammadex may increase the anticoagulant activities of Phenindione.	Approved
Sulbactam	Sulbactam may increase the anticoagulant activities of Phenindione.	Approved
Sulfadiazine	Sulfadiazine may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Sulfamethoxazole	Sulfamethoxazole may increase the anticoagulant activities of Phenindione.	Approved
Sulfasalazine	Sulfasalazine may increase the anticoagulant activities of Phenindione.	Approved
Sulfinpyrazone	The metabolism of Phenindione can be decreased when combined with Sulfinpyrazone.	Approved
Sulfisoxazole	Sulfisoxazole may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Sulindac	Sulindac may increase the anticoagulant activities of Phenindione.	Approved
Sulodexide	Phenindione may increase the anticoagulant activities of Sulodexide.	Approved, Investigational
Sultamicillin	Sultamicillin may increase the anticoagulant activities of Phenindione.	Investigational
Suprofen	Suprofen may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Synthetic Conjugated Estrogens, A	Synthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Phenindione.	Approved
Synthetic Conjugated Estrogens, B	Synthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Phenindione.	Approved
Tamoxifen	The serum concentration of Phenindione can be increased when it is combined with Tamoxifen.	Approved
Tazobactam	Tazobactam may increase the anticoagulant activities of Phenindione.	Approved
Tegafur	The serum concentration of Phenindione can be increased when it is combined with Tegafur.	Approved
Telithromycin	The serum concentration of Phenindione can be increased when it is combined with Telithromycin.	Approved
Temafloxacin	Temafloxacin may increase the anticoagulant activities of Phenindione.	Withdrawn
Tenecteplase	Tenecteplase may increase the anticoagulant activities of Phenindione.	Approved
Tenoxicam	Tenoxicam may increase the anticoagulant activities of Phenindione.	Approved
Teriflunomide	Teriflunomide may increase the anticoagulant activities of Phenindione.	Approved
Tesmilifene	Tesmilifene may increase the anticoagulant activities of Phenindione.	Investigational
Testosterone	Testosterone may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Tetracycline	Tetracycline may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Thiamylal	The metabolism of Phenindione can be increased when combined with Thiamylal.	Approved, Vet Approved
Thiopental	The metabolism of Phenindione can be increased when combined with Thiopental.	Approved, Vet Approved
Thyroid, porcine	Thyroid, porcine may increase the anticoagulant activities of Phenindione.	Approved
Tianeptine	Tianeptine may increase the anticoagulant activities of Phenindione.	Approved
Tiaprofenic acid	Tiaprofenic acid may increase the anticoagulant activities of Phenindione.	Approved
Tibolone	Tibolone may increase the anticoagulant activities of Phenindione.	Approved
Ticagrelor	Ticagrelor may increase the anticoagulant activities of Phenindione.	Approved
Ticarcillin	Ticarcillin may increase the anticoagulant activities of Phenindione.	Approved, Vet Approved
Ticlopidine	Ticlopidine may increase the anticoagulant activities of Phenindione.	Approved
Tinoridine	Tinoridine may increase the anticoagulant activities of Phenindione.	Investigational
Tinzaparin	Tinzaparin may increase the anticoagulant activities of Phenindione.	Approved
Tipranavir	Tipranavir may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Tirofiban	Tirofiban may increase the anticoagulant activities of Phenindione.	Approved
Tolazamide	Tolazamide may increase the anticoagulant activities of Phenindione.	Approved
Tolbutamide	Tolbutamide may increase the anticoagulant activities of Phenindione.	Approved
Tolfenamic Acid	Tolfenamic Acid may increase the anticoagulant activities of Phenindione.	Approved
Tolmetin	Tolmetin may increase the anticoagulant activities of Phenindione.	Approved
Toremifene	Toremifene may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Tositumomab	The risk or severity of adverse effects can be increased when Phenindione is combined with Tositumomab.	Approved
Tramadol	Tramadol may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Tranilast	Tranilast may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Trapidil	Trapidil may increase the anticoagulant activities of Phenindione.	Approved
Treprostinil	Treprostinil may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Triflusal	Triflusal may increase the anticoagulant activities of Phenindione.	Approved
Trimipramine	Trimipramine may increase the anticoagulant activities of Phenindione.	Approved
Trovafloxacin	Trovafloxacin may increase the anticoagulant activities of Phenindione.	Approved, Withdrawn
Ubidecarenone	Coenzyme Q10 may decrease the anticoagulant activities of Phenindione.	Experimental
Urokinase	Urokinase may increase the anticoagulant activities of Phenindione.	Approved, Investigational, Withdrawn
Valdecoxib	Valdecoxib may increase the anticoagulant activities of Phenindione.	Investigational, Withdrawn
Venlafaxine	The risk or severity of adverse effects can be increased when Venlafaxine is combined with Phenindione.	Approved
Vitamin E	Vitamin E may increase the anticoagulant activities of Phenindione.	Approved, Nutraceutical, Vet Approved
Vorapaxar	The risk or severity of adverse effects can be increased when Vorapaxar is combined with Phenindione.	Approved
Voriconazole	The serum concentration of Phenindione can be increased when it is combined with Voriconazole.	Approved, Investigational
Vorinostat	Vorinostat may increase the anticoagulant activities of Phenindione.	Approved, Investigational
Warfarin	Phenindione may increase the anticoagulant activities of Warfarin.	Approved
Ximelagatran	Phenindione may increase the anticoagulant activities of Ximelagatran.	Approved, Investigational, Withdrawn
Zafirlukast	The serum concentration of Phenindione can be increased when it is combined with Zafirlukast.	Approved, Investigational
Zaltoprofen	Zaltoprofen may increase the anticoagulant activities of Phenindione.	Approved
Zileuton	Zileuton may increase the anticoagulant activities of Phenindione.	Approved, Investigational, Withdrawn
Zimelidine	Zimelidine may increase the anticoagulant activities of Phenindione.	Withdrawn
Zomepirac	Zomepirac may increase the anticoagulant activities of Phenindione.	Withdrawn

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Link [Link]

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB14641
KEGG Compound	C07584
PubChem Compound	4760
PubChem Substance	46505018
ChemSpider	4596
BindingDB	50280157
ChEBI	8066
ChEMBL	CHEMBL711
Therapeutic Targets Database	DAP000769
PharmGKB	PA164784031
Wikipedia	Phenindione

ATC Codes

B01AA02 — Phenindione

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (62.6 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Completed	Prevention	Anticoagulation in Pregnancy	1

Pharmacoeconomics

Manufacturers

Sanofi aventis us llc

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	150 °C	PhysProp
water solubility	27 mg/L (at 20 °C)	Not Available
logP	2.90	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	0.023 mg/mL	ALOGPS
logP	3.1	ALOGPS
logP	2.88	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.23 m³·mol^-1	ChemAxon
Polarizability	23.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9816
Caco-2 permeable	+	0.7697
P-glycoprotein substrate	Non-substrate	0.7593
P-glycoprotein inhibitor I	Non-inhibitor	0.5461
P-glycoprotein inhibitor II	Non-inhibitor	0.8381
Renal organic cation transporter	Non-inhibitor	0.833
CYP450 2C9 substrate	Non-substrate	0.8036
CYP450 2D6 substrate	Non-substrate	0.9024
CYP450 3A4 substrate	Non-substrate	0.6947
CYP450 1A2 substrate	Inhibitor	0.9013
CYP450 2C9 inhibitor	Non-inhibitor	0.5714
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.7715
CYP450 3A4 inhibitor	Non-inhibitor	0.9141
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.598
Ames test	AMES toxic	0.7125
Carcinogenicity	Non-carcinogens	0.88
Biodegradation	Not ready biodegradable	0.8033
Rat acute toxicity	3.1041 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9414
hERG inhibition (predictor II)	Non-inhibitor	0.9008

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
MS	Mass Spectrum (Electron Ionization)	splash10-00di-4690000000-3b0da30c88d7d0ecf339	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as indanediones. These are compounds containing an indane ring bearing two ketone groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Aryl alkyl ketones / Beta-diketones / Benzene and substituted derivatives / Organic oxides / Hydrocarbon derivatives

Substituents

Indanedione / Aryl alkyl ketone / Aryl ketone / 1,3-diketone / 1,3-dicarbonyl compound / Monocyclic benzene moiety / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic ketone, beta-diketone (CHEBI:8066 )

Targets

Details

1. Vitamin K epoxide reductase complex subunit 1

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
Uniprot Name:: Vitamin K epoxide reductase complex subunit 1
Molecular Weight:: 18234.3 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Mentre F, Pousset F, Comets E, Plaud B, Diquet B, Montalescot G, Ankri A, Mallet A, Lechat P: Population pharmacokinetic-pharmacodynamic analysis of fluindione in patients. Clin Pharmacol Ther. 1998 Jan;63(1):64-78. [PubMed:9465843 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:49

Get DrugBank to go!

Structure for DB00498 (Phenindione)

Targets

References