RIVAROXABAN

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC B01AF01
UNII 9NDF7JZ4M3

Structure

InChI Key KGFYHTZWPPHNLQ-AWEZNQCLSA-N
Smiles O=C(NC[C@H]1CN(c2ccc(N3CCOCC3=O)cc2)C(=O)O1)c1ccc(Cl)s1
InChI
InChI=1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10-23(19(26)28-14)13-3-1-12(2-4-13)22-7-8-27-11-17(22)24/h1-6,14H,7-11H2,(H,21,25)/t14-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H18ClN3O5S
Molecular Weight 435.89
AlogP 2.52
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 88.18
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Coagulation factor X inhibitor INHIBITOR DailyMed
Protein: Coagulation factor X
Description: Coagulation factor X
Organism : Homo sapiens
P00742 ENSG00000126218
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- 1-700 - 0-3 15-55
Assay Description Organism Bioactivity Reference
In vitro inhibition of human coagulation factor Xa after incubation for 10 min at 25 degree C Homo sapiens 0.7 nM
Inhibition of Factor 10a None 0.4 nM
Inhibition of factor 10a None 0.7 nM Inhibition of factor 10a None 0.4 nM
Inhibition of human F10a using S-2765 as substrate after 45 mins Homo sapiens 1.6 nM
Inhibition of human factor 10a assessed as CBS 31.39 substrate hydrolysis by spectrophotometric analysis Homo sapiens 4.59 nM
Inhibition of human factor 10a assessed as CBS 31.39 substrate hydrolysis at 5 x 10'-9 M by spectrophotometric analysis Homo sapiens 52.0 %
Inhibition of F10a (unknown origin) using S-2222 as substrate incubated for 15 mins prior to substrate addition measured every 10 secs by spectrophotometric analysis Homo sapiens 0.66 nM
Inhibition of factor-10a (unknown origin) Homo sapiens 0.4 nM
Inhibition of factor 10a (unknown origin) Homo sapiens 0.7 nM
Inhibition of human factor 10a using N-Z-D-Arg-Gly-Arg-pNA, S-2765 chromogenic substrate Homo sapiens 8.52 nM
Inhibition of human F10a using S-2765 as substrate at 0.1 uM after 45 mins by spectra max analysis relative to control Homo sapiens 100.0 %
Inhibition of F10a in human plasma assessed as doubling of prothombin time Homo sapiens 400.0 nM
Inhibition of F10a in human plasma assessed as doubling of activated partial thromboplastin time Homo sapiens 700.0 nM
Inhibition of F10a in rabbit plasma assessed as doubling of prothombin time Oryctolagus cuniculus 510.0 nM
Inhibition of F10a in rabbit plasma assessed as doubling of activated partial thromboplastin time Oryctolagus cuniculus 860.0 nM
Inhibition of human F10a using S-2765 as substrate after 45 mins by spectra max analysis Homo sapiens 2.2 nM
Inhibition of human F10a using S-2765 as substrate preincubated for 10 mins followed by substrate addition by microplate reader analysis Homo sapiens 14.4 nM
Enzyme Inhibition Assay: The enzymatic activity of human factor Xa (FXa) was measured using the conversion of a chromogenic substrate specific for FXa. Factor Xa cleaves p-nitroaniline from the chromogenic substrate. The determinations were carried out in microtitre plates as follows.The test substances, in various concentrations, were dissolved in DMSO and incubated at 25 C. with human FXa (0.5 nmol/l dissolved in 50 mmol/l of tris buffer [C,C,C-tris(hydroxymethyl)-aminomethane], 150 mmol/l of NaCl, 0.1% BSA (bovine serum albumin), pH=8.3) for 10 minutes. Pure DMSO was used as control. The chromogenic substrate (150 umol 11 of Pefachrome FXa from Pentapharm) was then added. After an incubation time of 20 minutes at 25 C., the extinction at 405 nm was determined. Homo sapiens 700.0 nM Enzyme Inhibition Assay: The enzymatic activity of human factor Xa (FXa) was measured using the conversion of a chromogenic substrate specific for FXa. Factor Xa cleaves p-nitroaniline from the chromogenic substrate. The determinations were carried out in microtitre plates as follows.The test substances, in various concentrations, were dissolved in DMSO and incubated at 25 C. with human FXa (0.5 nmol/l dissolved in 50 mmol/l of tris buffer [C,C,C-tris(hydroxymethyl)-aminomethane], 150 mmol/l of NaCl, 0.1% BSA (bovine serum albumin), pH=8.3) for 10 minutes. Pure DMSO was used as control. The chromogenic substrate (150 umol 11 of Pefachrome FXa from Pentapharm) was then added. After an incubation time of 20 minutes at 25 C., the extinction at 405 nm was determined. Homo sapiens 1.4 nM
Inhibition of human factor 10a using pefachrome F10a as substrate preincubated for 10 mins followed by substrate addition and measured for 20 mins Homo sapiens 0.4 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 0.57 %
Inhibition of human activated Factor X using S-2765 as substrate incubated for 15 mins followed by substrate addition and measured after 1 hr by chromogenic assay Homo sapiens 3.4 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 27.81 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.06 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 1.373 %
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 0.03 % 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 -0.17 % 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 -0.14 % 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 -0.14 % 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 0.03 % 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 -0.17 %
Inhibition of human coagulation factor alpha-thrombin at 33 uM using Boc-Val-Pro-Arg-AMC as fluorogenic substrate measured at 1 min interval for 1 hr by fluorometric assay relative to control Homo sapiens 55.0 %
Inhibition of human coagulation factor alpha thrombin in presence of Boc-Val-Pro-Arg-AMC as fluorogenic substrate at 1 uM measured at 1 min interval for 1 hr by fluorometric assay relative to control Homo sapiens 15.0 %
Inhibition of human coagulation factor XIIA in presence of Boc-Gln-Gly-Arg-AMC as fluorogenic substrate at 1 uM measured at 1 min interval for 1 hr by fluorometric assay relative to control Homo sapiens -3.0 %
Inhibition of human coagulation factor Xa using Boc-Ile-Glu-Gly-Arg-AMC as fluorogenic substrate measured at 1 min interval for 1 hr by fluorometric assay Homo sapiens 0.7 nM

Related Entries

Cross References

Resources Reference
ChEBI 68579
ChEMBL CHEMBL198362
DrugBank DB06228
DrugCentral 4182
FDA SRS 9NDF7JZ4M3
Guide to Pharmacology 6388
KEGG D07086
PDB RIV
PubChem 9875401
SureChEMBL SCHEMBL3914
ZINC ZINC000003964126
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