Identification

Name
Phenprocoumon
Accession Number
DB00946  (APRD00228)
Type
Small Molecule
Groups
Approved, Investigational
Description

Coumarin derivative that acts as a long acting oral anticoagulant.

Structure
Thumb
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
International/Other Brands
Falithrom / Marcoumar / Marcumar
Categories
UNII
Q08SIO485D
CAS number
435-97-2
Weight
Average: 280.3178
Monoisotopic: 280.109944378
Chemical Formula
C18H16O3
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

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).

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
Human
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.

Route of elimination
Not Available
Half life

5-6 days

Clearance
Not Available
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).

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Phenprocoumon Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*2(C;T) / (T;T)T AlleleADR Directly StudiedThe presence of this polymorphism in CYP2C9 is associated with reduction in phenprocoumon metabolism.Details
Cytochrome P450 2C9CYP2C9*3(A;C) / (C;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
DrugInteraction
(1,2,6,7-3H)TestosteroneThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with (1,2,6,7-3H)Testosterone.
(R)-warfarinThe metabolism of Phenprocoumon can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Phenprocoumon can be decreased when combined with (S)-Warfarin.
1-TestosteroneThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with 1-Testosterone.
18-methyl-19-nortestosteroneThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with 18-methyl-19-nortestosterone.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Phenprocoumon.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Phenprocoumon.
3,5-diiodothyropropionic acidThe metabolism of Phenprocoumon can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Phenprocoumon.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Phenprocoumon.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015081
KEGG Drug
D05457
PubChem Compound
54680692
PubChem Substance
46506423
ChemSpider
10441592
BindingDB
768
ChEBI
50438
ChEMBL
CHEMBL1465
Therapeutic Targets Database
DAP000771
PharmGKB
PA450921
Wikipedia
Phenprocoumon
ATC Codes
B01AA04 — Phenprocoumon

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableMalignant Melanoma, Neoplasms1
2TerminatedTreatmentHaemorrhage / Thrombotic events1
3Active Not RecruitingTreatmentNonvalvular Atrial Fibrillation1
3Not Yet RecruitingTreatmentEnd-Stage Kidney Disease / Nonvalvular Atrial Fibrillation1
3TerminatedTreatmentNeoplasms / Venous Thromboembolism (VTE)1
3Unknown StatusNot AvailableDeep Venous Thrombosis1
4Active Not RecruitingBasic ScienceAtrial Fibrillation or Pulmonary Embolism / Existent Coronary or Valvular Calcification, or Both and Agatston Score > 50 in at Least One Location / Need of Long Term Oral Anticoagulation Therapy (OAT)1
4CompletedBasic ScienceAcute Coronary Syndromes (ACS) / Nonvalvular Atrial Fibrillation1
4CompletedTreatmentHip Replacement Postoperative / Knee Replacement Postoperative / Nonvalvular Atrial Fibrillation / Pulmonary Embolism (PE)1
4CompletedTreatmentNonvalvular Atrial Fibrillation2
4RecruitingPreventionNonvalvular Atrial Fibrillation1
4RecruitingTreatment(Atrial Fibrillation) or (Atrial Flutter) / Thrombosis of Left Atrial Appendage1
4RecruitingTreatmentCervical Artery Dissection1
4RecruitingTreatmentLeft Atrial Thrombosis / Nonvalvular Atrial Fibrillation1
4TerminatedTreatmentAcute Coronary Syndromes (ACS) / Atherosclerosis / Coronary Heart Disease (CHD) / Nonvalvular Atrial Fibrillation1
4TerminatedTreatmentMechanical Heart Valve Recipients1
4WithdrawnTreatmentCoronary Heart Disease (CHD) / Non ST Segment Elevation Myocardial Infarction (NSTEMI) / ST Elevation Myocardial Infarction (STEMI) / Stable Angina (SA) / Unstable Angina (UA)1
Not AvailableActive Not RecruitingNot AvailableNonvalvular Atrial Fibrillation1
Not AvailableCompletedNot AvailableNonvalvular Atrial Fibrillation3
Not AvailableCompletedNot AvailableUnsuspected Pulmonary Embolism1

Pharmacoeconomics

Manufacturers
  • Organon usa inc
Packagers
Not Available
Dosage forms
Not Available
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)6.44ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.64 m3·mol-1ChemAxon
Polarizability29.92 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
4-hydroxycoumarin / Benzopyran / 1-benzopyran / Phenylpropane / Pyranone / Monocyclic benzene moiety / Benzenoid / Pyran / Heteroaromatic compound / Vinylogous acid
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
hydroxycoumarin (CHEBI:50438)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17192772]
  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. [PubMed:16201835]
  3. Thijssen HH, Baars LG: Microsomal warfarin binding and vitamin K 2,3-epoxide reductase. Biochem Pharmacol. 1989 Apr 1;38(7):1115-20. [PubMed:2706010]
  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. [PubMed:3207986]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
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. 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. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. 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. [PubMed:15054565]
Kind
Protein
Organism
Human
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. [PubMed:19515014]
  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. [PubMed:17192772]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. 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. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. 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. [PubMed:15054565]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
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. [PubMed:1205658]
  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. [PubMed:12543492]
  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. [PubMed:1642965]
  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. [PubMed:2751413]
  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. [PubMed:4762907]
Kind
Protein
Organism
Human
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. [PubMed:11002825]
  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. [PubMed:16290938]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 05:30