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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=C1C=CC=C2)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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HEDULIN
Primary
HEDULIN

T1/2

ValueDoseCo-administeredAnalytePopulation
5 h
125 mg single, oral
PHENINDIONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
125 mg single, oral
PHENINDIONE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Record UNII
5M7Y6274ZE
Record Status Validated (UNII)
Record Version