U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O2
Molecular Weight 222.2387
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENINDIONE

SMILES

O=C1C(C(=O)C2=CC=CC=C12)C3=CC=CC=C3

InChI

InChIKey=NFBAXHOPROOJAW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H10O2
Molecular Weight 222.2387
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Phenindione is an anticoagulant which functions as a Vitamin K antagonist. The drug was discontinued in USA, but still in use worldwide.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HEDULIN

Approved Use

Phenindione is a synthetic anticoagulant which acts by interfering with the formation of factors II, VII, IX and X. It produces its effect in 36-48 hours after the initial dose; the effect wanes over a period of 48-72 hours after phenindione is stopped.
Primary
HEDULIN

Approved Use

Phenindione is a synthetic anticoagulant which acts by interfering with the formation of factors II, VII, IX and X. It produces its effect in 36-48 hours after the initial dose; the effect wanes over a period of 48-72 hours after phenindione is stopped.
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5 h
125 mg single, oral
dose: 125 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENINDIONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
125 mg single, oral
dose: 125 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENINDIONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg 1 times / day multiple, oral
Studied dose
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, 53 years
Health Status: unhealthy
Age Group: 53 years
Sex: M
Sources:
Disc. AE: Jaundice...
AEs leading to
discontinuation/dose reduction:
Jaundice (1 patient)
Sources:
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, 63 years
Health Status: unhealthy
Age Group: 63 years
Sex: M
Sources:
Disc. AE: Jaundice...
AEs leading to
discontinuation/dose reduction:
Jaundice (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Jaundice 1 patient
Disc. AE
75 mg 1 times / day multiple, oral
Studied dose
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, 53 years
Health Status: unhealthy
Age Group: 53 years
Sex: M
Sources:
Jaundice 1 patient
Disc. AE
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, 63 years
Health Status: unhealthy
Age Group: 63 years
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
slight or no effect
slight or no effect
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
PubMed

PubMed

TitleDatePubMed
Acute toxicity of diphacinone in Northern bobwhite: effects on survival and blood clotting.
2010-09
A novel prodrug strategy for beta-dicarbonyl carbon acids: syntheses and evaluation of the physicochemical characteristics of C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrug derivatives.
2010-06
[Glycopeptide-induced cutaneous adverse reaction].
2010-05
Validation of a new liquid chromatography- tandem mass spectrometry ion-trap technique for the simultaneous determination of thirteen anticoagulant rodenticides, drugs, or natural products.
2010-03
[Simultaneous determination of trace diphacinone and chlorophacinone in biological samples by high performance liquid chromatography coupled with ion trap mass spectrometry].
2010-02
[Thrombosis of the inferior vena cava revealing primary antiphospholipid syndrome: a case report].
2010-02
Formulation and evaluation of rizatriptan benzoate mouth disintegrating tablets.
2010-01
Effects of ion exchange resins in different mobile ion forms on semi-aerobic landfill leachate treatment.
2010
Budd-Chiari syndrome as a vascular complication of amebic liver abscess.
2009-11
[Inefficacy of vitamin K antagonists in an human immunodeficiency virus seropositive patient taking nevirapine].
2009-11
Taste masking of Etoricoxib by using ion-exchange resin.
2009-10-23
Use the INN to avoid confusion between drugs.
2009-10
[Severe overdose in vitamin K antagonist secondary to grapefruit juice absorption].
2009-10
Safety and efficacy of fondaparinux as an adjunctive treatment to thrombolysis in patients with high and intermediate risk pulmonary embolism.
2009-10
Potentiometric determination of ionisation constants for diphacinone and chlorophacinone in a dioxane-water cosolvent system.
2009-08-15
Formulation and optimization of sustained release tablets of venlafaxine resinates using response surface methodology.
2009-07
[Acute immuno-allergic interstitial nephritis after treatment with fluindione. Seven cases].
2009-07
A new VKORC1 mutation leading to an isolated resistance to fluindione.
2009-06
[Multidrug intoxication].
2009-03-20
[Liver infarcts with early HELLP syndrome and probable catastrophic antiphospholipid syndrome].
2009-03
[Necrotizing folliculitis in Behçet's disease].
2009-03
Combinatorial mutasynthesis of scrambled beauvericins, cyclooligomer depsipeptide cell migration inhibitors from Beauveria bassiana.
2009-01-26
Self-control of long-term oral anticoagulation using a point-of-care device.
2008-12-09
Analysis of indandione anticoagulant rodenticides in animal liver by eluent generator reagent free ion chromatography coupled with electrospray mass spectrometry.
2008-12-05
[Prospective study of oral anticoagulation control in 110 very elderly hospitalized patients and of risk factors for poor control].
2008-12
Chemical substructures that enrich for biological activity.
2008-11-01
[Hepatic and renal toxicity to fluindione (Previscan)].
2008-10
[Acute interstitial nephritis of fluindione: about three cases].
2008-10
Colchicine: serious interactions.
2008-08
Comparison of INR stability between self-monitoring and standard laboratory method: preliminary results of a prospective study in 67 mechanical heart valve patients.
2008-07-02
[Fluindione-induced acute generalised exanthematous pustulosis confirmed by patch testing].
2008-04
Severe hemorrhagic syndrome due to similarity of drug names.
2008-03
Evaluation of the palatability of three nonsteroidal antiinflammatory top-dress formulations in horses.
2008
Taste mask, design and evaluation of an oral formulation using ion exchange resin as drug carrier.
2008
[Modification of an antitumor action of photodynamic therapy with anticoagulant drug fenylin].
2007-12-27
Iron and manganese contamination: sources, adverse effects and control methods.
2007-10
Potentiation of fluindione or warfarin by dexamethasone in multiple myeloma and AL amyloidosis.
2007-10
Acute thrombosis of a prosthetic mitral valve: a lesson in anticoagulation.
2007-08
Conservative treatment of spontaneous and isolated dissection of mesenteric arteries.
2007-07-30
[Liver toxicity associated with oral anticoagulant treatment: report of two cases].
2007-07-25
Development and evaluation of oral controlled release chlorpheniramine-ion exchange resinate suspension.
2007-05-05
[Advice for patients taking oral anticoagulants (coumadin or Previscan)].
2007-04-15
Identification of selective ion-exchange resin for fluoride sorption.
2007-04-15
Descriptive analysis of the process and quality of oral anticoagulation management in real-life practice in patients with chronic non-valvular atrial fibrillation: the international study of anticoagulation management (ISAM).
2007-04
Can cryoglobulins interfere with the measurement of IgM antiphosphatidylethanolamine antibodies by ELISA?
2007
Sustained release of propranolol hydrochloride based on ion-exchange resin entrapped within polystyrene microcapsules.
2006-12
Acute immuno-allergic interstitial nephritis caused by fluindione.
2006-12
A green method for the electroorganic synthesis of new 1,3-Indandione derivatives.
2006-10
Vitamin K antagonists and pregnancy outcome. A multi-centre prospective study.
2006-06
Preparation and in vitro evaluation of polystyrene-coated diltiazem-resin complex by oil-in-water emulsion solvent evaporation method.
2006-05-26
Patents

Patents

Sample Use Guides

Initial: orally 200 mg in 2 equal doses on day 1, then 100 mg on day 2. Maintenance: 50-150 mg/day.
Route of Administration: Oral
In Vitro Use Guide
Experiments for determination of inhibition of vitamin-K-dependent carboxylation was determined using preparation of rat liver microsomes. Experimental reaction mixtures contained both vitamin K and a vitamin K antagonist. The control reaction mixture contained 3.00 ml of microsomal suspension, 0.81 ml of buffer II. 1.20 ml of an ATP-generating system, 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 m.V/) in buffer II. 0.060 ml of NaH[14C]O3 (1.0 uCi/uL added 0.5 min prior to reaction initiation) and at the time of reaction initiation 0.030 ml of vitamin K (final concentration 20 ug/ml) diluted in 0.85% sodium chloride solution. Reaction mixtures were equilibrated at 27 °C in a reciprocating shaker water bath at 100 excursions per minute. Serial samples (0.45 ml each) were collected from each control and blank reaction tube at 2,4, 6, 8, 10, 12, 14, 16, 30, 60, 90 and 120 min, and from each experimental reaction tube at 2,4, 6, 8, 10, 12, 14 and 16 min. Each sample was transferred to a tube containing I ml of ice-cold 10% TCA. Amount of product formed was determined using liquid scintillation spectrometer with the external standard method of quench correction. Phenindione inhibits Vitamin K-dependent carboxylation with IC50 of 19 uM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:52 GMT 2025
Record UNII
5M7Y6274ZE
Record Status Validated (UNII)
Record Version
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Name Type Language
PHENINDIONE
HSDB   INN   MART.   MI   ORANGE BOOK   USP-RS   WHO-DD  
INN  
Official Name English
DANILONE
Preferred Name English
PHENINDIONE [MI]
Common Name English
PHENINDIONE [HSDB]
Common Name English
HEDULIN
Brand Name English
NSC-41693
Code English
1H-INDENE-1,3(2H)-DIONE, 2-PHENYL-
Systematic Name English
2-Phenyl-1,3-indandione
Systematic Name English
PHENINDIONE [ORANGE BOOK]
Common Name English
PHENINDIONE [MART.]
Common Name English
phenindione [INN]
Common Name English
Phenindione [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC B01AA02
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
WHO-VATC QB01AA02
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
NCI_THESAURUS C263
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
Code System Code Type Description
RXCUI
8130
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C66371
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
EVMPD
SUB09765MIG
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
WIKIPEDIA
PHENINDIONE
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
NSC
41693
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
MESH
D010630
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-454-4
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
DRUG BANK
DB00498
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
INN
23
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
SMS_ID
100000082255
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
CAS
83-12-5
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
ChEMBL
CHEMBL711
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
FDA UNII
5M7Y6274ZE
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
PUBCHEM
4760
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
HSDB
3155
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
DRUG CENTRAL
2130
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023453
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
CHEBI
8066
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
MERCK INDEX
m8618
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY Merck Index
IUPHAR
6838
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY