Phenprocoumon

Identification

Summary

Phenprocoumon is an anticoagulant drug used for the prevention of thrombosis.

Generic Name
Phenprocoumon
DrugBank Accession Number
DB00946
Background

Coumarin derivative that acts as a long-acting oral anticoagulant.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 280.3178
Monoisotopic: 280.109944378
Chemical Formula
C18H16O3
Synonyms
  • 3-(1-Phenylpropyl)-4-hydroxycoumarin
  • 3-(1'-Phenyl-propyl)-4-oxycoumarin
  • 3-(alpha-Ethylbenzyl)-4-hydroxycoumarin
  • 3-(alpha-Phenylpropyl)-4-hydroxycoumarin
  • 4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one
  • 4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
  • Fenprocumon
  • Fenprocumone
  • Phenprocoumarol
  • Phenprocoumarole
  • Phenprocoumon
  • Phenprocoumone
  • Phenprocoumonum
  • Phenprocumone

Pharmacology

Indication

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 (AF).

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prevention ofEmbolism venous••••••••••••••••••
Treatment ofEmbolism venous••••••••••••••••••
Treatment ofMyocardial infarction••••••••••••••••••
Prevention ofThrombotic events••••••••••••••••••
Treatment ofThrombotic events••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Phenprocoumon, a coumarin anticoagulant, thins the blood by antagonizing vitamin K which is required for the production of clotting factors in the liver. Anticoagulants such as phenprocoumon 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.

Mechanism of action

Phenprocoumon 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.

TargetActionsOrganism
AVitamin K epoxide reductase complex subunit 1
inhibitor
Humans
Absorption

Bioavailability is close to 100%

Volume of distribution

Not Available

Protein binding

99%

Metabolism

Phenprocoumon is stereoselectively metabolized by hepatic microsomal enzymes (cytochrome P-450) to inactive hydroxylated metabolites (predominant route) and by reductases to reduced metabolites. Cytochrome P450 2C9 is the principal form of human liver P-450 responsible for metabolism.

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Route of elimination

Not Available

Half-life

5-6 days

Clearance

Not Available

Adverse Effects
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Toxicity

50=500 mg/kg. Symptoms of overdose includes suspected or overt abnormal bleeding (e.g., appearance of blood in stools or urine, hematuria, excessive menstrual bleeding, melena, petechiae, excessive bruising or persistent oozing from superficial injuries).

Pathways
PathwayCategory
Phenprocoumon Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*2(T;T) / (C;T)T AlleleADR Directly StudiedThe presence of this polymorphism in CYP2C9 is associated with reduction in phenprocoumon metabolism.Details
Cytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleADR Directly StudiedThe presence of this polymorphism in CYP2C9 is associated with reduction in phenprocoumon metabolism.Details
Vitamin K epoxide reductase complex subunit 1---(A;A) / (A;G)G > AADR Directly StudiedThe presence of this polymorphism in VKORC1 is associated with reduction in phenprocoumon metabolism.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*15Not Available485C>AADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*3Not Available1075A>CADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*8Not Available449G>AADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*13Not Available269T>CADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*14Not Available374G>AADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*16Not Available895A>GADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all ADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*26Not Available389C>GADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*28Not Available641A>TADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details
Cytochrome P450 2C9CYP2C9*33Not Available395G>AADR InferredAssociated with delayed stabilization. If carrier of rs9934438 as well, increased risk of severe overanticoagulation.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Phenprocoumon can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Phenprocoumon can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Phenprocoumon.
AbirateroneThe metabolism of Phenprocoumon can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Phenprocoumon.
Food Interactions
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
  • Ensure consistent Vitamin K intake. Changes in vitamin K intake may impact coagulation.
  • Exercise caution with grapefruit products.
  • Exercise caution with St. John's Wort.

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International/Other Brands
Falithrom / Liquamar / Marcoumar / Marcumar

Categories

ATC Codes
B01AA04 — Phenprocoumon
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Coumarins and derivatives
Sub Class
Hydroxycoumarins
Direct Parent
4-hydroxycoumarins
Alternative Parents
1-benzopyrans / Phenylpropanes / Pyranones and derivatives / Vinylogous acids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
1-benzopyran / 4-hydroxycoumarin / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Heteroaromatic compound / Hydrocarbon derivative / Lactone / Monocyclic benzene moiety / Organic oxide
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
hydroxycoumarin (CHEBI:50438)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Q08SIO485D
CAS number
435-97-2
InChI Key
DQDAYGNAKTZFIW-UHFFFAOYSA-N
InChI
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
IUPAC Name
4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
SMILES
CCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2

References

General References
Not Available
Human Metabolome Database
HMDB0015081
KEGG Drug
D05457
PubChem Compound
54680692
PubChem Substance
46506423
ChemSpider
10441592
BindingDB
768
RxNav
8150
ChEBI
50438
ChEMBL
CHEMBL1465
Therapeutic Targets Database
DAP000771
PharmGKB
PA450921
Wikipedia
Phenprocoumon

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Organon usa inc
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral3 mg
Tablet, film coatedOral1.5 mg
TabletOral
TabletOral3 MG
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)179.5 °CPhysProp
water solubility12.9 mg/LNot Available
logP3.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0486 mg/mLALOGPS
logP3.81ALOGPS
logP3.74Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)5.67Chemaxon
pKa (Strongest Basic)-6.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area46.53 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity81.64 m3·mol-1Chemaxon
Polarizability29.95 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.992
Blood Brain Barrier+0.8992
Caco-2 permeable+0.8924
P-glycoprotein substrateSubstrate0.5545
P-glycoprotein inhibitor INon-inhibitor0.8579
P-glycoprotein inhibitor IINon-inhibitor0.8896
Renal organic cation transporterNon-inhibitor0.8798
CYP450 2C9 substrateNon-substrate0.6832
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.687
CYP450 1A2 substrateInhibitor0.6462
CYP450 2C9 inhibitorInhibitor0.7572
CYP450 2D6 inhibitorNon-inhibitor0.9555
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorNon-inhibitor0.9032
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6013
Ames testNon AMES toxic0.8363
CarcinogenicityNon-carcinogens0.9044
BiodegradationNot ready biodegradable0.8477
Rat acute toxicity3.1784 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9105
hERG inhibition (predictor II)Non-inhibitor0.9479
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.9 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0gk9-1390000000-b8adf6e29e27ba0e0032
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-2290000000-0d6599c4696e72fbdea5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0190000000-012c3078c2affc17020b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001l-6790000000-50fad2b50efc58d22627
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-0490000000-f821148c92ff29771a10
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ku-9700000000-821f2ae829f4932fa3d7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-010u-6920000000-8f47a578fa0104d2e9b5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.5128415
predicted
DarkChem Lite v0.1.0
[M-H]-165.07245
predicted
DeepCCS 1.0 (2019)
[M+H]+175.3638415
predicted
DarkChem Lite v0.1.0
[M+H]+167.43045
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.9700415
predicted
DarkChem Lite v0.1.0
[M+Na]+173.5236
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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...
Gene Name
VKORC1
Uniprot ID
Q9BQB6
Uniprot Name
Vitamin K epoxide reductase complex subunit 1
Molecular Weight
18234.3 Da
References
  1. Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [Article]
  2. Reitsma PH, van der Heijden JF, Groot AP, Rosendaal FR, Buller HR: A C1173T dimorphism in the VKORC1 gene determines coumarin sensitivity and bleeding risk. PLoS Med. 2005 Oct;2(10):e312. Epub 2005 Oct 11. [Article]
  3. Thijssen HH, Baars LG: Microsomal warfarin binding and vitamin K 2,3-epoxide reductase. Biochem Pharmacol. 1989 Apr 1;38(7):1115-20. [Article]
  4. Thijssen HH, Baars LG, Vervoort-Peters HT: Vitamin K 2,3-epoxide reductase: the basis for stereoselectivity of 4-hydroxycoumarin anticoagulant activity. Br J Pharmacol. 1988 Nov;95(3):675-82. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Ufer M, Svensson JO, Krausz KW, Gelboin HV, Rane A, Tybring G: Identification of cytochromes P450 2C9 and 3A4 as the major catalysts of phenprocoumon hydroxylation in vitro. Eur J Clin Pharmacol. 2004 May;60(3):173-82. doi: 10.1007/s00228-004-0740-5. Epub 2004 Mar 31. [Article]
  2. Visser LE, van Schaik RH, van Vliet M, Trienekens PH, De Smet PA, Vulto AG, Hofman A, van Duijn CM, Stricker BH: The risk of bleeding complications in patients with cytochrome P450 CYP2C9*2 or CYP2C9*3 alleles on acenocoumarol or phenprocoumon. Thromb Haemost. 2004 Jul;92(1):61-6. doi: 10.1160/TH03-12-0741. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [Article]
  3. Daly AK, King BP: Contribution of CYP2C9 to variability in vitamin K antagonist metabolism. Expert Opin Drug Metab Toxicol. 2006 Feb;2(1):3-15. doi: 10.1517/17425255.2.1.3 . [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ufer M, Svensson JO, Krausz KW, Gelboin HV, Rane A, Tybring G: Identification of cytochromes P450 2C9 and 3A4 as the major catalysts of phenprocoumon hydroxylation in vitro. Eur J Clin Pharmacol. 2004 May;60(3):173-82. doi: 10.1007/s00228-004-0740-5. Epub 2004 Mar 31. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
Regulator
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Niedner R, von Oettingen U, Meyer F: [The reciprocal actions of phenprocoumon (Marcumar) with human serum albumin, erythrocytes and blood]. Int J Clin Pharmacol Biopharm. 1975 Dec;12(4):446-57. [Article]
  2. Fitos I, Visy J, Simonyi M: Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods. J Biochem Biophys Methods. 2002 Dec 31;54(1-3):71-84. [Article]
  3. Fitos I, Simonyi M: Stereoselective effect of phenprocoumon enantiomers on the binding of benzodiazepines to human serum albumin. Chirality. 1992;4(1):21-3. [Article]
  4. Rehse K, Fiedler B: [Determination of the protein binding of drugs by continuous ultrafiltration. 9. Comparison of the binding of nonsteroid antirheumatics to human serum albumin and their interaction with phenprocoumon]. Arch Pharm (Weinheim). 1989 Apr;322(4):241-3. [Article]
  5. Niedner R, von Oettingen U, Meyer F: [Binding of phenprocoumarol (Marcumar) to human albumin]. Int J Clin Pharmacol. 1973 Oct;8(2):160-6. [Article]
  6. Watanabe H, Yamasaki K, Kragh-Hansen U, Tanase S, Harada K, Suenaga A, Otagiri M: In vitro and in vivo properties of recombinant human serum albumin from Pichia pastoris purified by a method of short processing time. Pharm Res. 2001 Dec;18(12):1775-81. doi: 10.1023/a:1013391001141. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Otagiri M, Maruyama T, Imai T, Imamura Y: Fluorescent investigations of binding of phenprocoumon to alpha 1-acid glycoprotein. J Pharm Sci. 1987 Aug;76(8):646-9. [Article]
  2. Hazai E, Visy J, Fitos I, Bikadi Z, Simonyi M: Selective binding of coumarin enantiomers to human alpha1-acid glycoprotein genetic variants. Bioorg Med Chem. 2006 Mar 15;14(6):1959-65. Epub 2005 Nov 15. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:46