NAV

Lefradafiban

Identification

Generic Name
Lefradafiban
DrugBank Accession Number
DB04863
Background

Lefradafiban is an oral platelet glycoprotein IIb/IIIa receptor antagonist being investigated in the treatment of angina.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 439.4611
Monoisotopic: 439.174335547
Chemical Formula
C23H25N3O6
Synonyms
  • Lefradafibán
  • Lefradafiban
  • Léfradafiban
  • Lefradafibanum
External IDs
  • FP-007SE

Pharmacology

Indication

For the treatment of unstable angina.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Lefradafiban, an orally active prodrug of fradafiban, is a novel glycoprotein (IIb/IIIa) inhibitor for the treatment of unstable angina. Development was discontinued in 2000 due to lack of efficacy.

Mechanism of action

GPIIb/IIIa inhibitors, such as lefradafiban, block the final common pathway of platelet aggregation.

TargetActionsOrganism
UIntegrin alpha-IIbNot AvailableHumans
UIntegrin beta-3Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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.
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Isosorbide mononitrateLefradafiban may increase the vasodilatory activities of Isosorbide mononitrate.
Patent BlueThe therapeutic efficacy of Lefradafiban can be decreased when used in combination with Patent Blue.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Pyrrolines / Cyclic carboximidic acids / Methyl esters / Lactims / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds
show 7 more
Substituents
Alkyl aryl ether / Amidine / Aromatic heteromonocyclic compound / Azacycle / Biphenyl / Carbonic acid derivative / Carbonyl group / Carboximidamide / Carboxylic acid amidine / Carboxylic acid derivative
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
methyl ester, pyrrolidin-2-ones (CHEBI:60634)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0R4888YXR5
CAS number
149503-79-7
InChI Key
PGCFXITVMNNKON-ROUUACIJSA-N
InChI
InChI=1S/C23H25N3O6/c1-30-20(27)12-17-11-18(25-22(17)28)13-32-19-9-7-15(8-10-19)14-3-5-16(6-4-14)21(24)26-23(29)31-2/h3-10,17-18H,11-13H2,1-2H3,(H,25,28)(H2,24,26,29)/t17-,18-/m0/s1
IUPAC Name
methyl 2-[(3S,5S)-5-{[(4'-{[(methoxycarbonyl)amino]methanimidoyl}-[1,1'-biphenyl]-4-yl)oxy]methyl}-2-oxopyrrolidin-3-yl]acetate
SMILES
[H][C@@]1(COC2=CC=C(C=C2)C2=CC=C(C=C2)C(=N)NC(=O)OC)C[C@@H](CC(=O)OC)C(=O)N1

References

General References
  1. Akkerhuis KM, van Den Brand MJ, van Der Zwaan C, Peels HO, Suryapranata H, van Der Wieken LR, Stibbe J, Hoffmann J, Baardman T, Deckers JW, Simoons ML: Pharmacodynamics and safety of lefradafiban, an oral platelet glycoprotein IIb/IIIa receptor antagonist, in patients with stable coronary artery disease undergoing elective angioplasty. Heart. 2001 Apr;85(4):444-50. [Article]
  2. Doggrell SA: Clinical trials with glycoprotein IIb/IIIa antagonists - No benefit without bleeding? Drugs Today (Barc). 2001 Aug;37(8):509-531. [Article]
PubChem Compound
9576916
PubChem Substance
175426872
ChemSpider
7851357
ChEBI
60634
ChEMBL
CHEMBL2105032

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Subjects (HS)3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0288 mg/mLALOGPS
logP2.16ALOGPS
logP2.06Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)10.16Chemaxon
pKa (Strongest Basic)2.32Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area126.81 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity125.97 m3·mol-1Chemaxon
Polarizability47.28 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9954
Blood Brain Barrier+0.5605
Caco-2 permeable-0.7001
P-glycoprotein substrateSubstrate0.5684
P-glycoprotein inhibitor INon-inhibitor0.8028
P-glycoprotein inhibitor IIInhibitor0.509
Renal organic cation transporterNon-inhibitor0.7191
CYP450 2C9 substrateNon-substrate0.7478
CYP450 2D6 substrateNon-substrate0.8114
CYP450 3A4 substrateSubstrate0.582
CYP450 1A2 substrateNon-inhibitor0.6713
CYP450 2C9 inhibitorNon-inhibitor0.7755
CYP450 2D6 inhibitorNon-inhibitor0.8675
CYP450 2C19 inhibitorNon-inhibitor0.6173
CYP450 3A4 inhibitorNon-inhibitor0.5688
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6038
Ames testNon AMES toxic0.643
CarcinogenicityNon-carcinogens0.8891
BiodegradationNot ready biodegradable0.9819
Rat acute toxicity2.5767 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9859
hERG inhibition (predictor II)Non-inhibitor0.8247
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Targets

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Details1. Integrin alpha-IIb
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Integrin alpha-IIb/beta-3 is a receptor for fibronectin, fibrinogen, plasminogen, prothrombin, thrombospondin and vitronectin. It recognizes the sequence R-G-D in a wide array of ligands. It recogn...
Gene Name
ITGA2B
Uniprot ID
P08514
Uniprot Name
Integrin alpha-IIb
Molecular Weight
113375.96 Da
References
  1. Akkerhuis KM, van Den Brand MJ, van Der Zwaan C, Peels HO, Suryapranata H, van Der Wieken LR, Stibbe J, Hoffmann J, Baardman T, Deckers JW, Simoons ML: Pharmacodynamics and safety of lefradafiban, an oral platelet glycoprotein IIb/IIIa receptor antagonist, in patients with stable coronary artery disease undergoing elective angioplasty. Heart. 2001 Apr;85(4):444-50. [Article]
Details2. Integrin beta-3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Integrin alpha-V/beta-3 (ITGAV:ITGB3) is a receptor for cytotactin, fibronectin, laminin, matrix metalloproteinase-2, osteopontin, osteomodulin, prothrombin, thrombospondin, vitronectin and von Wil...
Gene Name
ITGB3
Uniprot ID
P05106
Uniprot Name
Integrin beta-3
Molecular Weight
87056.975 Da
References
  1. Akkerhuis KM, van Den Brand MJ, van Der Zwaan C, Peels HO, Suryapranata H, van Der Wieken LR, Stibbe J, Hoffmann J, Baardman T, Deckers JW, Simoons ML: Pharmacodynamics and safety of lefradafiban, an oral platelet glycoprotein IIb/IIIa receptor antagonist, in patients with stable coronary artery disease undergoing elective angioplasty. Heart. 2001 Apr;85(4):444-50. [Article]

Drug created at October 19, 2007 22:06 / Updated at February 21, 2021 18:51