TIROFIBAN

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Synonyms
Status
Molecule Category Free-form
ATC B01AC17
UNII GGX234SI5H
EPA CompTox DTXSID20162730

Structure

InChI Key COKMIXFXJJXBQG-NRFANRHFSA-N
Smiles CCCCS(=O)(=O)N[C@@H](Cc1ccc(OCCCCC2CCNCC2)cc1)C(=O)O
InChI
InChI=1S/C22H36N2O5S/c1-2-3-16-30(27,28)24-21(22(25)26)17-19-7-9-20(10-8-19)29-15-5-4-6-18-11-13-23-14-12-18/h7-10,18,21,23-24H,2-6,11-17H2,1H3,(H,25,26)/t21-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H36N2O5S
Molecular Weight 440.61
AlogP 2.95
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 14.0
Polar Surface Area 104.73
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 30.0
Assay Description Organism Bioactivity Reference
Inhibition of human alphaIIb-beta3 integrin in platelet aggregation assay Homo sapiens 15.0 nM
Equilibrium dissociation constant was measured from displacement of L-762,745 from Fibrinogen receptor of human platelets by flow cytometry Homo sapiens 15.0 nM
Compound was evaluated for inhibition against Fibrinogen Receptor. None 9.0 nM
Inhibition of [125I]fibrinogen binding to fibrinogen receptor Homo sapiens 5.0 nM
Inhibition of ADP-mediated platelet aggregation in human gel-filtered platelets Homo sapiens 10.0 nM
In vitro inhibition of ADP-mediated human gel filtered platelet aggregation. Homo sapiens 11.0 nM
In vitro inhibition of ADP-induced human platelet aggregation. Homo sapiens 11.0 nM
The compound was tested in vivo for the inhibition of aggregation of human gel-filtered platelets(GFP) Homo sapiens 11.0 nM
Inhibition of human gel filtered platelet aggregation stimulated by ADP (10 mM) Homo sapiens 18.0 nM
Inhibition of platelet aggregation as the concentration necessary to inhibit the change in light. Homo sapiens 9.0 nM
Binding affinity to resting form of alpha IIb/beta3 integrin by flow cytometry using fluorescein ligand L-726,745 displacement from human platelets. None 13.0 nM
Competition with [1251]L-692,884 for binding to purified alpha IIb/beta3 integrin, activated by coating onto yttrium silicate scintillation proximity assay fluomicrospheres. None 1.9 nM
Binding affinity against alpha IIb beta-3 integrin in the presence of L-736622. None 13.0 nM
Inhibition of aggregation of human gel-filtered platelets measured by light transmittance method at 37 degrees C. Homo sapiens 15.0 nM
Inhibition of platelet aggregation Homo sapiens 35.7 nM
Displacement of biotinylated fibrinogen from human alpha2b-beta3 receptor after 2 hrs by chemiluminescence assay Homo sapiens 0.37 nM
Displacement of extracellular matrix protein fibrinogen from human integrin alpha2bbeta3 after 1 hr by competitive ELISA Homo sapiens 0.95 nM
Inhibition of integrin alpha2bbeta3-mediated platelet aggregation in human TRAP-6-activated whole blood for 6 mins by impedence-based aggregometry Homo sapiens 13.6 nM
Inhibition of fibrinogen binding to Integrin alpha2bbeta3 receptor (unknown origin) by competitive ELISA Homo sapiens 0.95 nM
Displacement of biotinylated fibrinogen from human glycoprotein 2b/3a receptor after 2 hrs by chemiluminescence assay Homo sapiens 0.37 nM
Inhibition of FITC-labeled fibrinogen binding to integrin alpha2bbeta3 receptor in human platelets by flow cytometry Homo sapiens 2.4 nM
Inhibition of ADP-induced human platelet aggregation in platelet-rich plasma by Born's method Homo sapiens 32.0 nM
Inhibition of alpha2beta3 receptor (unknown origin) assessed as inhibition of platelet adhesion at 10 uM Homo sapiens 88.0 %
Binding affinity to alpha2b/beta3 integrin (unknown origin) Homo sapiens 600.0 nM
Inhibition of FITC-labeled fibrinogen binding to integrin alpha2bbeta3 open form in human washed platelets Homo sapiens 2.4 nM
Antagonist activity against integrin alpha2bbeta3 open form in human platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation Homo sapiens 32.0 nM
Inhibition of FITC-labeled fibrinogen binding to integrin alpha2bbeta3 closed form in human washed platelets Homo sapiens 2.4 nM
Antagonist activity against integrin alpha2bbeta3 closed form in human platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation Homo sapiens 32.0 nM
Antiplatelet activity in human platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation by Born's method Homo sapiens 30.0 nM
Inhibition of FITC-labelled fibrinogen binding to integrin alpha2b beta3 receptor in human platelet cells Homo sapiens 1.9 nM
Antagonist activity at GP2b/GP3a receptor in human platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation preincubated for 1 min followed by ADP addition by aggregometric method Homo sapiens 90.0 nM
Displacement of fibrinogen from human platelet GP2b/GP3a receptor after 2 hrs by ELISA Homo sapiens 40.0 nM
Inhibition of human fibronectin binding to human Integrin alpha2b beta3 receptor incubated for 1 hr by ELISA Homo sapiens 1.3 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 9.58 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.08 %
Inhibition of human integrin alphavbeta3 (unknown origin) Homo sapiens 11.0 nM
Inhibition of fibrinogen binding to human platelet integrin alpha2b beta3 by ELISA based solid phase binding assay Homo sapiens 1.2 nM
Inhibition of fibrinogen binding to alpha2bbeta3 isolated from human HEL cells incubated for 1 hr by scintillation-proximity assay based competitive solid-phase binding assay Homo sapiens 7.3 nM
Antagonist activity at alpha2bbeta3 in human HEL cells assessed as reduction in cell adhesion to fibrinogen pre-incubated for 30 mins before fibrinogen and further incubated for 1 hr by nitrophenyl-N-acetyl-beta-D-glucosaminide substrate based chromogenic assay Homo sapiens 9.4 nM
Binding affinity to human integrin alpha2bbeta3 incubated for 1 hr by ELISA based solid phase integrin binding assay None 1.2 nM
Inhibition of fibrinogen binding to rat platelet integrin alpha2b beta3 by ELISA based solid phase binding assay Rattus norvegicus 130.0 nM Inhibition of fibrinogen binding to rat platelet integrin alpha2b beta3 by ELISA based solid phase binding assay Rattus norvegicus 0.06 ug.mL-1

Cross References

Resources Reference
ChEBI 9605
ChEMBL CHEMBL916
DrugBank DB00775
DrugCentral 2680
FDA SRS GGX234SI5H
Human Metabolome Database HMDB0014913
Guide to Pharmacology 6586
KEGG C07965
PDB AGG
PharmGKB PA451698
PubChem 60947
SureChEMBL SCHEMBL3685
ZINC ZINC000003806104
CONTENTS