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
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
| 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 |
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1930 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3781349 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | HEDULIN Approved UsePhenindione 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 UsePhenindione 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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse 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 |
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 |
Disc. AE: Jaundice... AEs leading to discontinuation/dose reduction: Jaundice (1 patient) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
| 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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/ Page: 2.0 |
slight or no effect | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/ Page: 2.0 |
slight or no effect |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/ Page: 11.0 |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/ Page: 11.0 |
likely |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3781349
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
Edited
Mon Mar 31 17:46:52 GMT 2025
by
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| Record UNII |
5M7Y6274ZE
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-ATC |
B01AA02
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WHO-VATC |
QB01AA02
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NCI_THESAURUS |
C263
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8130
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C66371
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SUB09765MIG
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PHENINDIONE
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201-454-4
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DB00498
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83-12-5
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CHEMBL711
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m8618
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6838
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