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Details

Stereochemistry RACEMIC
Molecular Formula C18H16O3
Molecular Weight 280.3178
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENPROCOUMON

SMILES

CCC(C1=CC=CC=C1)C2=C(O)C3=C(OC2=O)C=CC=C3

InChI

InChIKey=DQDAYGNAKTZFIW-UHFFFAOYSA-N
InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3

HIDE SMILES / InChI

Molecular Formula C18H16O3
Molecular Weight 280.3178
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Phenprocoumon is the dominant anticoagulant in clinical use in several continental European countries. It used for the prevention and treatment of thromboembolic disease including venous thrombosis, thromboembolism, and pulmonary embolism as well as for the prevention of ischemic stroke in patients with atrial fibrillation. Phenprocoumon inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). Bleedings are the most important side -effects of oral anticoagulants. The gastrointestinal and the urinary tract are often affected; the most dangerous are intracerebral hemorrhages. A great number of drugs increase the risk of bleeding of oral anticoagulants. Enzyme inhibitors (e.g. allopurinol, androgens, cimetidine, ciprofloxacin, co-trimoxazole, certain anti-inflammatory agents, fibrates, imidazoles, macrolide antibiotics, etc.) reinforce, and enzyme inducers (e.g. barbiturates, rifampicin) and oral contraceptives reduce, the anticoagulant action.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
LIQUAMAR
Preventing
LIQUAMAR
Preventing
LIQUAMAR
Preventing
LIQUAMAR

Cmax

ValueDoseCo-administeredAnalytePopulation
2.1 μM
12 mg single, oral
PHENPROCOUMON, (S)- plasma
Homo sapiens
2 μM
12 mg single, oral
PHENPROCOUMON, (R)- plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
105.1 μg × h/mL
12 mg single, oral
PHENPROCOUMON, (S)- plasma
Homo sapiens
89.7 μg × h/mL
12 mg single, oral
PHENPROCOUMON, (R)- plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
149 h
12 mg single, oral
PHENPROCOUMON, (S)- plasma
Homo sapiens
123 h
12 mg single, oral
PHENPROCOUMON, (R)- plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
1st day single dose - 12-15 mg, 2nd day single dose - 6-9 mg. Treatment continues with lower doses - 1.5 - 6 mg daily as a maintenance dose.
Route of Administration: Oral
In Vitro Use Guide
At a given cholestyramine concentration (0.1 gm/100 rnI) the percentage phenprocoumon bound remained nearly constant in the 1 to 75 fLg/ml concentration range of phenprocoumon.
Substance Class Chemical
Record UNII
Q08SIO485D
Record Status Validated (UNII)
Record Version