RIVASTIGMINE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N06DA03
UNII PKI06M3IW0
EPA CompTox DTXSID7023564

Structure

InChI Key XSVMFMHYUFZWBK-NSHDSACASA-N
Smiles CCN(C)C(=O)Oc1cccc([C@H](C)N(C)C)c1
InChI
InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H22N2O2
Molecular Weight 250.34
AlogP 2.76
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 4.0
Polar Surface Area 32.78
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 18.0

Bioactivity

Mechanism of Action Action Reference
Cholinesterases; ACHE & BCHE inhibitor INHIBITOR FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 37-48000 - 5680 25-100
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor epsilon subunit
- 9000 - - 2
Membrane receptor
- - - - 18
Assay Description Organism Bioactivity Reference
In vitro inhibitory concentration against purified Acetylcholinesterase of human erythrocytes; value ranges from 0.74-1.2 None 920.0 nM
In vitro inhibitory concentration against Butyrylcholinesterase of horse serum; value ranges from 0.81-0.86 Equus caballus 830.0 nM
Ex vivo inhibition of human plasma Butyrylcholinesterase. None 37.0 nM
Inhibitory concentration against human serum butyrylcholinesterase activity Homo sapiens 301.0 nM
Inhibitory concentration against human plasma Butyrylcholinesterase Homo sapiens 37.0 nM
In vitro inhibitory concentration against butyrylcholinesterase was determined using rat serum homogenate Rattus norvegicus 350.0 nM
Anticholinesterase activity against human plasma BChE Homo sapiens 37.0 nM
Inhibition of human recombinant butyrylcholinesterase Homo sapiens 30.1 nM
Inhibition of human AChE-induced amyloid beta (1-40) aggregation at 100 uM Homo sapiens 5.0 %
Inhibition of self-induced amyloid beta (1-40) aggregation at 10 uM by thioflavin T based fluorometric assay Homo sapiens 17.8 %
Inhibition of human AchE Homo sapiens 920.0 nM
Inhibition of Torpedo californica AChE assessed as carbamylation Torpedo californica 2.0 /min/M
Inhibition of human serum BuchE after 20 mins by Ellman's method Homo sapiens 300.0 nM
Inhibition of BChE in human serum assessed as hydrolysis of butyrylthiocholine by Ellman's method Homo sapiens 170.0 nM
Inhibition of BChE in human serum assessed as hydrolysis of butyrylthiocholine at 100 ug/mL by Ellman's method Homo sapiens 100.0 %
Inhibition of BChE in human serum assessed as hydrolysis of butyrylthiocholine at 10 ug/mL by Ellman's method Homo sapiens 100.0 %
Inhibition of BChE in human serum assessed as hydrolysis of butyrylthiocholine at 1 ug/mL by Ellman's method Homo sapiens 100.0 %
Inhibition of BChE in human serum assessed as hydrolysis of butyrylthiocholine at 0.1 ug/mL by Ellman's method Homo sapiens 76.0 %
Inhibition of BuChE None 37.0 nM
Inhibition of horse serum BChE preincubated for 5 mins by Ellman's method Equus caballus 831.76 nM
Inhibition of AChE-induced amyloid beta aggregation None 54.0 nM
Inhibition of BChE None 49.0 nM
Inhibition of purified human plasma BuChE preincubated for 30 mins before DTNB substrate addition by spectrophotometric assay based Ellman's method Homo sapiens 179.0 nM
Inhibition of total plasma cholinesterase in rat at 5 mg/kg, po measured 30 to 180 mins post dose Rattus norvegicus 39.0 %
Inhibition of total brain cholinesterase activity in rat at 5 mg/kg, po measured 30 to 180 mins post dose Rattus norvegicus 56.0 %
Inhibition of human erythrocytes BChE Homo sapiens 37.0 nM
Inhibition of human plasma BChE Homo sapiens 37.0 nM
Inhibition of human serum recombinant BChE after 20 mins using butyrylthiocholine iodide as a substrate by Ellman's assay Homo sapiens 301.0 nM
Inhibition of human serum BuChE using butyrylthiocholine iodide as substrate preincubated for 90 mins before substrate addition by Ellman's method Homo sapiens 301.0 nM
Inhibition of equine BuChE after 120 mins by Ellman's method Equus caballus 160.0 nM
Inhibition of bovine AChE after 120 mins by Ellman's method Bos taurus 620.0 nM
Inhibition of butyrylcholinesterase (unknown origin) Homo sapiens 300.0 nM
Inhibition of acetylcholinesterase (unknown origin) Homo sapiens 700.0 nM
Inhibition of human BuChE using butyrylthiocholine as substrate by Ellman's method Homo sapiens 300.0 nM
Inhibition of BuChE (unknown origin) using butyrylthiocholine iodide as substrate incubated for 25 mins by Ellman's method Homo sapiens 260.0 nM
Inhibition of recombinant human BChE by Ellman method Homo sapiens 30.0 nM
Inhibition of BChE in rat serum using butyrylthiocholine iodide substrate incubated for 15 mins by UV spectroscopy based Ellman's method Rattus norvegicus 370.0 nM
Inhibition of AChE (unknown origin) Homo sapiens 54.0 nM
Pseudo-irreversible inhibition of Torpedo californica AChE using acetylthiocholine as substrate by cornish bowden plot analysis Torpedo californica 2.0 /M/min
Inhibition of human serum BuChE using acetylthiocholine iodide as substrate preincubated for 20 to 60 mins followed by substrate addition by Ellman's method Homo sapiens 301.0 nM
Inhibition of human serum BChE using S-Butyrylthiocholine iodide as substrate preincubated for 15 mins followed by substrate addition by Ellman's method Homo sapiens 380.0 nM
Inhibition of AChE (unknown origin) at 1 uM using acetylthiocholine iodide as substrate preincubated for 60 mins followed by substrate addition measured after 5 mins by Ellman's method relative to control Homo sapiens 6.77 %
Inhibition of AChE (unknown origin) at 5 uM using acetylthiocholine iodide as substrate preincubated for 60 mins followed by substrate addition measured after 5 mins by Ellman's method relative to control Homo sapiens 15.56 %
Inhibition of BuChE (unknown origin) at 1 uM using acetylthiocholine iodide as substrate preincubated for 60 mins followed by substrate addition measured after 5 mins by Ellman's method relative to control Homo sapiens 61.04 %
Inhibition of BuChE (unknown origin) at 5 uM using acetylthiocholine iodide as substrate preincubated for 60 mins followed by substrate addition measured after 5 mins by Ellman's method relative to control Homo sapiens 92.99 %
Inhibition of butyrylcholinesterase (unknown origin) using butyrylthiocholine iodide as substrate after 25 mins by Ellmann method Homo sapiens 260.0 nM
Inhibition of human BuChE using butyrylthiocholine as substrate after 1 min by Ellman's method Homo sapiens 370.0 nM
Inhibition of BuChE (unknown origin) at 500 nM pre-incubated for 20 mins before S-Butyrylthiocholine iodide substrate addition by Ellman reagent based spectrophotometry Homo sapiens 30.08 %
Inhibition of AChE (unknown origin) at 500 nM pre-incubated for 20 mins before acetylthiocholine iodide substrate addition by Ellman reagent based spectrophotometry Homo sapiens 1.92 %
Inhibition of BuChE (unknown origin) pre-incubated for 20 mins before S-Butyrylthiocholine iodide substrate addition by Ellman reagent based spectrophotometry Homo sapiens 678.0 nM
Inhibition of BChE (unknown origin) Homo sapiens 30.0 nM
Inhibition of AChE in human erythrocytes preincubated for 60 mins followed by substrate addition by Ellman's method Homo sapiens 920.0 nM
Inhibition of human serum BChE using butyrylthiocholine iodide as substrate preincubated for 20 to 60 mins followed by substrate addition by Ellman's method Homo sapiens 301.0 nM
Inhibition of electric eel AChE at 50 nM using acetylthiocholine iodide as substrate preincubated for 60 mins followed by substrate addition measured for 5 mins by Ellman's method Electrophorus electricus 2.59 %
Inhibition of equine serum BChE at 50 nM using acetylthiocholine iodide as substrate preincubated for 60 mins followed by substrate addition measured for 5 mins by Ellman's method Equus caballus 54.66 %
Inhibition of human serum BChE using butyrylthiocholine as substrate by Ellman's assay Homo sapiens 300.0 nM
Inhibition of equine serum BuChE using butyrylthiocholine iodide as substrate preincubated with enzyme for 20 mins followed by substrate addition by Ellman's method Equus caballus 560.0 nM
Inhibition of equine BuChE using ACTI as substrate preincubated for 29 mins followed by substrate addition measured at 1 min intervals for 10 mins by Ellman's assay Equus caballus 495.0 nM
Inhibition of human BuChE using ACTI as substrate incubated for 40 mins measured at 1 min intervals for 10 mins by Ellman's assay Homo sapiens 803.0 nM
Inhibition of mouse plasma BuChE using S-butyrylacetylthiocholine iodide as substrate at 10 uM measured after 30 mins by Ellman's method relative to control Mus musculus 93.15 %
Inhibition of mouse plasma BuChE using S-butyrylacetylthiocholine iodide as substrate measured after 30 mins by Ellman's method relative to control Mus musculus 58.0 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 9.94 %
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 -0.03 %
In-vivo inhibition of AChE in human brain at 0.6 mg/kg, ip relative to control Homo sapiens 40.0 %
In-vivo inhibition of BuChE in human brain at 0.6 mg/kg, ip relative to control Homo sapiens 25.0 %
Inhibition of equine serum BChE using S-butyrylthiocholine iodide as substrate preincubated for 60 mins followed by substrate addition and measured for 5 mins by Ellman's method Equus caballus 785.0 nM
Inhibition of rat bone marrow myeloperoxidase using H2O2 as substrate at 10 uM after 20 mins by TMB based method (Rvb = - 1.4 +/- 12.7%) Rattus norvegicus 17.1 %
Inhibition of Electrophorus electricus AChE at 100 uM using acetylthiocholine iodide as substrate preincubated for 30 mins followed by substrate addition and measured after 10 mins by Ellman's method (Rvb = 7 +/- 7.1%) Electrophorus electricus 59.6 %
Inhibition of equine serum BuChE using butyrylthiocholine iodide as substrate preincubated with enzyme for 20 mins followed by addition of substrate and measured after 20 mins by DTNB reagent based Ellman's method Equus caballus 560.0 nM
In vivo inhibition of AChE in ICR mouse assessed as reduction in enzyme activity in cerebral cortex at 2 mg/kg, ig via gavage measured after 30 mins using acetylthiocholine iodide as substrate by DTNB reagent based assay Mus musculus 49.9 %
Inhibition of human BuChE using S-butyrylthiocholine as substrate preincubated for 30 mins followed by substrate addition and measured after 25 mins by DTNB-reagent based spectrophotometric method Homo sapiens 37.0 nM
Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate preincubated with enzyme for 10 mins followed by substrate addition and measured by Ellman's method Homo sapiens 60.0 nM
Inhibition of human serum BuChE using butyrylthiocholine iodide as substrate preincubated with enzyme for 10 mins followed by substrate addition and measured by Ellman's method Homo sapiens 14.3 nM
Inhibition of recombinant human BuChe using S-butyrylthiocholine iodide as substrate measured after 7 mins by Ellman's method Homo sapiens 300.0 nM
Inhibition of human AChE using acetylthiocholine iodide as substrate at 20 uM preincubated with enzyme for 5 mins followed by substrate addition and measured after 5 mins by Ellman's method Homo sapiens 12.2 %
Antioxidant activity assessed as DPPH radical scavenging activity at 100 uM incubated for 2 hrs by microplate reader method None 2.5 %
Inhibition of equine serum BuChE using butyrylthiocholine iodide as substrate preincubated with enzyme for 20 mins followed by substrate addition and measured after 20 mins by Ellman's method Equus caballus 58.0 nM
Inhibition of HFIP-pretreated human recombinant amyloid beta (1 to 42) self aggregation at 10 uM incubated up to 48 hrs under shaking condition and measured every 3 min by Thioflavin T based fluorescence assay relative to control Homo sapiens 86.6 %
Primary screen in NF54 nanoGlo assay, in single point, at 2uM, 72h Plasmodium falciparum 7.0 %

Environmental Exposure

Environmental Exposure Map
Countries
Czech Republic
Germany
Hungary
Romania
Serbia
Slovenia

Cross References

Resources Reference
ChEBI 8874
ChEMBL CHEMBL636
DrugBank DB00989
DrugCentral 2392
FDA SRS PKI06M3IW0
Human Metabolome Database HMDB0015124
Guide to Pharmacology 6602
KEGG C11766
PharmGKB PA451262
PubChem 77991
SureChEMBL SCHEMBL2764
ZINC ZINC000000004413
CONTENTS