Page last updated: 2024-12-06

lamifiban

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

lamifiban: a nonpeptide glycoprotein IIb/IIIa antagonist; prevents platelet loss during experimental cardiopulmonary bypass [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3038484
CHEMBL ID108111
CHEBI ID177737
SCHEMBL ID4683
MeSH IDM0223481

Synonyms (36)

Synonym
CHEBI:177737
2-[1-[(2s)-2-[(4-carbamimidoylbenzoyl)amino]-3-(4-hydroxyphenyl)propanoyl]piperidin-4-yl]oxyacetic acid
lamifiban
lamstat
ro-44-9883
ro-44-9883/023
ro-44-9883/000
144412-49-7
((1-(n-(p-amidinobenzoyl)-l-tyrosyl)-4-piperidyl)oxy)acetic acid
lamifiban [usan:inn]
acetic acid, ((1-(2-((4-aminoiminomethyl)benzoyl)amino)-3-(4-hydroxyphenyl)-1-oxopropyl)-4-piperidinyl)oxy)-, (s)-
acetic acid, ((1-(2-((4-(aminoiminomethyl)benzoyl)amino)-3-(4-hydroxyphenyl)-1-oxopropyl)-4-piperidinyl)oxy)-, (s)-
ro 44-9883/000
CHEMBL108111 ,
{1-[2-(4-carbamimidoyl-benzoylamino)-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid (ro 44-9883)
bdbm50003874
{1-[2-(4-carbamimidoyl-benzoylamino)-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid (ro 44-9883 (lamifiban))
{1-[(s)-2-(4-carbamimidoyl-benzoylamino)-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid
9xoe28082s ,
unii-9xoe28082s
FPKOGTAFKSLZLD-FQEVSTJZSA-N
[[1-[n-(p-amidinobenzoyl)-l-tyrosyl]-4-piperidinyl]oxy]acetic acid
SCHEMBL4683
lamifiban [who-dd]
lamifiban [mart.]
lamifiban [usan]
lamifiban [inn]
lamifiban [mi]
DTXSID20869939
ro 44-9883; ro 44-9883/000
2-((1-((4-carbamimidoylbenzoyl)-l-tyrosyl)piperidin-4-yl)oxy)acetic acid
Q27273359
(s)-2-((1-(2-(4-carbamimidoylbenzamido)-3-(4-hydroxyphenyl)propanoyl)piperidin-4-yl)oxy)acetic acid
({1-[n-(4-carbamimidoylbenzoyl)-l-tyrosyl]piperidin-4-yl}oxy)acetic acid
NB9 ,
AKOS040746984

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"Relating pharmacokinetic information obtained in animal species to man (interspecies scaling) can play an important role in enabling understanding of the differences and similarities between species, and helping to predict the kinetic profile of a new compound in man."( Animal pharmacokinetics and interspecies scaling from animals to man of lamifiban, a new platelet aggregation inhibitor.
Brandt, R; Chou, RC; Coassolo, P; Lave, T; Saner, A; Schmitt-Hoffmann, AH, 1996
)
0.29
"Human pharmacokinetic parameters are often predicted prior to clinical study from in vivo preclinical pharmacokinetic data."( Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
Jolivette, LJ; Ward, KW, 2005
)
0.33
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" The patients in Group 3 were sensitized to the antiplatelet effect allowing an 18-fold dosage reduction without compromising the pharmacodynamics."( Increased potency and decreased elimination of lamifiban, a GPIIb-IIIa antagonist, in patients with severe renal dysfunction.
Brosstad, F; Goggin, T; Lehne, G; Midtvedt, K; Nordal, KP, 1998
)
0.3
"To determine if lamifiban, dosed according to creatinine clearance, could decrease the rates of death, myocardial infarction, or refractory ischemia, a randomized, double-blind, placebo-controlled trial was undertaken."( Patient-specific dosing of IIb/IIIa antagonists during acute coronary syndromes: rationale and design of the PARAGON B study. The PARAGON B International Steering Committee.
Moliterno, DJ, 2000
)
0.31
"The plasma concentration of small-molecule IIb/IIIa inhibitors is strongly influenced by renal function, and renal-specific dosing of these agents may improve outcome among patients with acute coronary syndromes."( Patient-specific dosing of IIb/IIIa antagonists during acute coronary syndromes: rationale and design of the PARAGON B study. The PARAGON B International Steering Committee.
Moliterno, DJ, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylglycineAn N-acyl-amino acid in which amino acid specified is glycine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Integrin beta-3Homo sapiens (human)IC50 (µMol)0.01570.00010.632310.0000AID225586; AID32981
Integrin alpha-IIbHomo sapiens (human)IC50 (µMol)0.01570.00010.730910.0000AID225586; AID32981
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (70)

Processvia Protein(s)Taxonomy
negative regulation of low-density lipoprotein receptor activityIntegrin beta-3Homo sapiens (human)
positive regulation of protein phosphorylationIntegrin beta-3Homo sapiens (human)
positive regulation of endothelial cell proliferationIntegrin beta-3Homo sapiens (human)
positive regulation of cell-matrix adhesionIntegrin beta-3Homo sapiens (human)
cell-substrate junction assemblyIntegrin beta-3Homo sapiens (human)
cell adhesionIntegrin beta-3Homo sapiens (human)
cell-matrix adhesionIntegrin beta-3Homo sapiens (human)
integrin-mediated signaling pathwayIntegrin beta-3Homo sapiens (human)
embryo implantationIntegrin beta-3Homo sapiens (human)
blood coagulationIntegrin beta-3Homo sapiens (human)
positive regulation of endothelial cell migrationIntegrin beta-3Homo sapiens (human)
positive regulation of gene expressionIntegrin beta-3Homo sapiens (human)
negative regulation of macrophage derived foam cell differentiationIntegrin beta-3Homo sapiens (human)
positive regulation of fibroblast migrationIntegrin beta-3Homo sapiens (human)
negative regulation of lipid storageIntegrin beta-3Homo sapiens (human)
response to activityIntegrin beta-3Homo sapiens (human)
smooth muscle cell migrationIntegrin beta-3Homo sapiens (human)
positive regulation of smooth muscle cell migrationIntegrin beta-3Homo sapiens (human)
platelet activationIntegrin beta-3Homo sapiens (human)
positive regulation of vascular endothelial growth factor receptor signaling pathwayIntegrin beta-3Homo sapiens (human)
cell-substrate adhesionIntegrin beta-3Homo sapiens (human)
activation of protein kinase activityIntegrin beta-3Homo sapiens (human)
negative regulation of lipid transportIntegrin beta-3Homo sapiens (human)
regulation of protein localizationIntegrin beta-3Homo sapiens (human)
regulation of actin cytoskeleton organizationIntegrin beta-3Homo sapiens (human)
cell adhesion mediated by integrinIntegrin beta-3Homo sapiens (human)
positive regulation of cell adhesion mediated by integrinIntegrin beta-3Homo sapiens (human)
positive regulation of osteoblast proliferationIntegrin beta-3Homo sapiens (human)
heterotypic cell-cell adhesionIntegrin beta-3Homo sapiens (human)
substrate adhesion-dependent cell spreadingIntegrin beta-3Homo sapiens (human)
tube developmentIntegrin beta-3Homo sapiens (human)
wound healing, spreading of epidermal cellsIntegrin beta-3Homo sapiens (human)
cellular response to platelet-derived growth factor stimulusIntegrin beta-3Homo sapiens (human)
apolipoprotein A-I-mediated signaling pathwayIntegrin beta-3Homo sapiens (human)
wound healingIntegrin beta-3Homo sapiens (human)
apoptotic cell clearanceIntegrin beta-3Homo sapiens (human)
regulation of bone resorptionIntegrin beta-3Homo sapiens (human)
positive regulation of angiogenesisIntegrin beta-3Homo sapiens (human)
positive regulation of bone resorptionIntegrin beta-3Homo sapiens (human)
symbiont entry into host cellIntegrin beta-3Homo sapiens (human)
platelet-derived growth factor receptor signaling pathwayIntegrin beta-3Homo sapiens (human)
positive regulation of fibroblast proliferationIntegrin beta-3Homo sapiens (human)
mesodermal cell differentiationIntegrin beta-3Homo sapiens (human)
positive regulation of smooth muscle cell proliferationIntegrin beta-3Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylationIntegrin beta-3Homo sapiens (human)
negative regulation of lipoprotein metabolic processIntegrin beta-3Homo sapiens (human)
negative chemotaxisIntegrin beta-3Homo sapiens (human)
regulation of release of sequestered calcium ion into cytosolIntegrin beta-3Homo sapiens (human)
regulation of serotonin uptakeIntegrin beta-3Homo sapiens (human)
angiogenesis involved in wound healingIntegrin beta-3Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeIntegrin beta-3Homo sapiens (human)
platelet aggregationIntegrin beta-3Homo sapiens (human)
cellular response to mechanical stimulusIntegrin beta-3Homo sapiens (human)
cellular response to xenobiotic stimulusIntegrin beta-3Homo sapiens (human)
positive regulation of glomerular mesangial cell proliferationIntegrin beta-3Homo sapiens (human)
blood coagulation, fibrin clot formationIntegrin beta-3Homo sapiens (human)
maintenance of postsynaptic specialization structureIntegrin beta-3Homo sapiens (human)
regulation of postsynaptic neurotransmitter receptor internalizationIntegrin beta-3Homo sapiens (human)
regulation of postsynaptic neurotransmitter receptor diffusion trappingIntegrin beta-3Homo sapiens (human)
positive regulation of substrate adhesion-dependent cell spreadingIntegrin beta-3Homo sapiens (human)
positive regulation of adenylate cyclase-inhibiting opioid receptor signaling pathwayIntegrin beta-3Homo sapiens (human)
regulation of trophoblast cell migrationIntegrin beta-3Homo sapiens (human)
regulation of extracellular matrix organizationIntegrin beta-3Homo sapiens (human)
cellular response to insulin-like growth factor stimulusIntegrin beta-3Homo sapiens (human)
negative regulation of endothelial cell apoptotic processIntegrin beta-3Homo sapiens (human)
positive regulation of T cell migrationIntegrin beta-3Homo sapiens (human)
cell migrationIntegrin beta-3Homo sapiens (human)
positive regulation of leukocyte migrationIntegrin alpha-IIbHomo sapiens (human)
cell-matrix adhesionIntegrin alpha-IIbHomo sapiens (human)
integrin-mediated signaling pathwayIntegrin alpha-IIbHomo sapiens (human)
angiogenesisIntegrin alpha-IIbHomo sapiens (human)
cell-cell adhesionIntegrin alpha-IIbHomo sapiens (human)
cell adhesion mediated by integrinIntegrin alpha-IIbHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (21)

Processvia Protein(s)Taxonomy
fibroblast growth factor bindingIntegrin beta-3Homo sapiens (human)
C-X3-C chemokine bindingIntegrin beta-3Homo sapiens (human)
insulin-like growth factor I bindingIntegrin beta-3Homo sapiens (human)
neuregulin bindingIntegrin beta-3Homo sapiens (human)
virus receptor activityIntegrin beta-3Homo sapiens (human)
fibronectin bindingIntegrin beta-3Homo sapiens (human)
protease bindingIntegrin beta-3Homo sapiens (human)
protein disulfide isomerase activityIntegrin beta-3Homo sapiens (human)
protein kinase C bindingIntegrin beta-3Homo sapiens (human)
platelet-derived growth factor receptor bindingIntegrin beta-3Homo sapiens (human)
integrin bindingIntegrin beta-3Homo sapiens (human)
protein bindingIntegrin beta-3Homo sapiens (human)
coreceptor activityIntegrin beta-3Homo sapiens (human)
enzyme bindingIntegrin beta-3Homo sapiens (human)
identical protein bindingIntegrin beta-3Homo sapiens (human)
vascular endothelial growth factor receptor 2 bindingIntegrin beta-3Homo sapiens (human)
metal ion bindingIntegrin beta-3Homo sapiens (human)
cell adhesion molecule bindingIntegrin beta-3Homo sapiens (human)
extracellular matrix bindingIntegrin beta-3Homo sapiens (human)
fibrinogen bindingIntegrin beta-3Homo sapiens (human)
protein bindingIntegrin alpha-IIbHomo sapiens (human)
identical protein bindingIntegrin alpha-IIbHomo sapiens (human)
metal ion bindingIntegrin alpha-IIbHomo sapiens (human)
extracellular matrix bindingIntegrin alpha-IIbHomo sapiens (human)
molecular adaptor activityIntegrin alpha-IIbHomo sapiens (human)
fibrinogen bindingIntegrin alpha-IIbHomo sapiens (human)
integrin bindingIntegrin alpha-IIbHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (30)

Processvia Protein(s)Taxonomy
glutamatergic synapseIntegrin beta-3Homo sapiens (human)
nucleusIntegrin beta-3Homo sapiens (human)
nucleoplasmIntegrin beta-3Homo sapiens (human)
plasma membraneIntegrin beta-3Homo sapiens (human)
cell-cell junctionIntegrin beta-3Homo sapiens (human)
focal adhesionIntegrin beta-3Homo sapiens (human)
external side of plasma membraneIntegrin beta-3Homo sapiens (human)
cell surfaceIntegrin beta-3Homo sapiens (human)
apical plasma membraneIntegrin beta-3Homo sapiens (human)
platelet alpha granule membraneIntegrin beta-3Homo sapiens (human)
lamellipodium membraneIntegrin beta-3Homo sapiens (human)
filopodium membraneIntegrin beta-3Homo sapiens (human)
microvillus membraneIntegrin beta-3Homo sapiens (human)
ruffle membraneIntegrin beta-3Homo sapiens (human)
integrin alphav-beta3 complexIntegrin beta-3Homo sapiens (human)
melanosomeIntegrin beta-3Homo sapiens (human)
synapseIntegrin beta-3Homo sapiens (human)
postsynaptic membraneIntegrin beta-3Homo sapiens (human)
extracellular exosomeIntegrin beta-3Homo sapiens (human)
integrin alphaIIb-beta3 complexIntegrin beta-3Homo sapiens (human)
glycinergic synapseIntegrin beta-3Homo sapiens (human)
integrin complexIntegrin beta-3Homo sapiens (human)
protein-containing complexIntegrin beta-3Homo sapiens (human)
alphav-beta3 integrin-PKCalpha complexIntegrin beta-3Homo sapiens (human)
alphav-beta3 integrin-IGF-1-IGF1R complexIntegrin beta-3Homo sapiens (human)
alphav-beta3 integrin-HMGB1 complexIntegrin beta-3Homo sapiens (human)
receptor complexIntegrin beta-3Homo sapiens (human)
alphav-beta3 integrin-vitronectin complexIntegrin beta-3Homo sapiens (human)
alpha9-beta1 integrin-ADAM8 complexIntegrin beta-3Homo sapiens (human)
focal adhesionIntegrin beta-3Homo sapiens (human)
cell surfaceIntegrin beta-3Homo sapiens (human)
synapseIntegrin beta-3Homo sapiens (human)
plasma membraneIntegrin alpha-IIbHomo sapiens (human)
focal adhesionIntegrin alpha-IIbHomo sapiens (human)
cell surfaceIntegrin alpha-IIbHomo sapiens (human)
platelet alpha granule membraneIntegrin alpha-IIbHomo sapiens (human)
extracellular exosomeIntegrin alpha-IIbHomo sapiens (human)
integrin alphaIIb-beta3 complexIntegrin alpha-IIbHomo sapiens (human)
blood microparticleIntegrin alpha-IIbHomo sapiens (human)
integrin complexIntegrin alpha-IIbHomo sapiens (human)
external side of plasma membraneIntegrin alpha-IIbHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID540217Volume of distribution at steady state in dog after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID73164Inhibition of fibrinogen binding to immobilized fibrinogen receptor1992Journal of medicinal chemistry, Nov-13, Volume: 35, Issue:23
Low molecular weight, non-peptide fibrinogen receptor antagonists.
AID540218Clearance in monkey after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID158086Compound was tested for inhibition of platelet aggregation of human platelet rich plasma(h-PRP) induced by adenosine 5-diphosphate (ADP)1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Orally active fibrinogen receptor antagonists. 2. Amidoximes as prodrugs of amidines.
AID540216Clearance in dog after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID225586Inhibition of platelet aggregation2000Journal of medicinal chemistry, Sep-21, Volume: 43, Issue:19
Platelet glycoprotein IIb-IIIa antagonists as prototypical integrin blockers: novel parenteral and potential oral antithrombotic agents.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540214Clearance in rat after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID223375Inhibition of platelet aggregation in human-platelet rich plasma(h-PRP) induced by adenosine 5'-diphosphate-(ADP)1992Journal of medicinal chemistry, Nov-13, Volume: 35, Issue:23
Low molecular weight, non-peptide fibrinogen receptor antagonists.
AID540220Clearance in human after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID217303Inhibition of fibrinogen binding to immobilized vitronectin receptor1992Journal of medicinal chemistry, Nov-13, Volume: 35, Issue:23
Low molecular weight, non-peptide fibrinogen receptor antagonists.
AID32981Inhibition of FG binding to alpha IIb beta-3 integrin1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Orally active fibrinogen receptor antagonists. 2. Amidoximes as prodrugs of amidines.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540215Volume of distribution at steady state in rat after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID223376Inhibition of platelet aggregation in human-platelet rich plasma(h-PRP) induced by collagen1992Journal of medicinal chemistry, Nov-13, Volume: 35, Issue:23
Low molecular weight, non-peptide fibrinogen receptor antagonists.
AID130476Inhibition of platelet aggregation of human platelet rich plasma(h-PRP) induced by adenosine 5-diphosphate (ADP).(oral activity in mice)1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Orally active fibrinogen receptor antagonists. 2. Amidoximes as prodrugs of amidines.
AID540221Volume of distribution at steady state in human after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID223377Inhibition of platelet aggregation in human-platelet rich plasma(h-PRP) induced by thrombin1992Journal of medicinal chemistry, Nov-13, Volume: 35, Issue:23
Low molecular weight, non-peptide fibrinogen receptor antagonists.
AID540219Volume of distribution at steady state in monkey after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (78)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's40 (51.28)18.2507
2000's36 (46.15)29.6817
2010's2 (2.56)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (14.29%)5.53%
Reviews35 (41.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other37 (44.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]