PHYSOSTIGMINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC S01EB05 V03AB19
UNII 9U1VM840SP
EPA CompTox DTXSID3023471

Structure

InChI Key PIJVFDBKTWXHHD-HIFRSBDPSA-N
Smiles CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN(C)[C@@H]1N2C
InChI
InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H21N3O2
Molecular Weight 275.35
AlogP 1.77
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 44.81
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 20.0
Assay Description Organism Bioactivity Reference
Compound was evaluated for the inhibition of acetylcholinesterase (AChE) in electric eel Electrophorus electricus 46.0 nM
Compound was evaluated for the inhibition of acetylcholinesterase (AChE) in Torpedo californica Torpedo californica 46.0 nM
Compound was evaluated for the inhibition of acetylcholinesterase (AChE) in bovine brain None 146.0 nM
Compound was evaluated for the inhibition of acetylcholinesterase (AChE) in bovine erythrocytes None 123.0 nM
Concentration required to inhibit hydrolytic activity of Acetylcholinesterase by 50% None 30.0 nM
In vitro inhibitory activity against acetylcholinesterase from electric eel eel 61.0 nM
Inhibition of acetylcholinesterase (AChE) in electric eel (type V-S) by modified radiometric assay Electrophorus electricus 275.0 nM
Inhibitory activity against acetylcholinesterase as a prodrug was demonstarted Electrophorus electricus 1.0 nM
Inhibitory activity against Acetylcholinesterase in electric eel Electrophorus electricus 28.0 nM
In vitro inhibition of Acetylcholinesterase from human erythrocytes None 19.0 nM
Anticholinesterase activity against erythrocyte acetylcholinesterase (AChE) in humans. None 27.9 nM
In vitro inhibition of human erythrocyte Acetylcholinesterase. None 14.1 nM
Evaluated for the in vitro inhibition of the Acetylcholinesterase (AChE) from human erythrocytes None 19.0 nM
Compound was evaluated for the inhibition of acetylcholinesterase (AChE) in human erythrocytes None 47.0 nM
Concentration required to inhibit 50% of Acetylcholinesterase obtained from human erythrocytes was determined in vitro None 18.9 nM
Concentration required to inhibit acetylcholinesterase isolated from human erythrocytes None 128.0 nM
In vitro inhibition of human acetylcholinesterase. None 43.0 nM
Inhibition of acetylcholinesterase (AChE) of human red blood cell (type XIII) by modified radiometric AChE assay Homo sapiens 61.0 nM
Inhibition of Acetylcholinesterase (AChE) from human RBC Homo sapiens 30.0 nM
In vitro inhibitory activity against human acetylcholinesterase Homo sapiens 128.0 nM
In vitro inhibitory activity against human AchE (Acetylcholinesterase) None 128.0 nM
Inhibitory activity against Acetylcholinesterase None 57.0 nM
Inhibition of human acetylcholinesterase from erythrocytes (RBC) Homo sapiens 27.9 nM
In vitro inhibition of human erythrocyte acetylcholinesterase. None 28.0 nM
Inhibitory activity against Acetylcholinesterase in cortex Homo sapiens 31.0 nM
Inhibitory activity against Acetylcholinesterase in erythrocyte Homo sapiens 35.0 nM
The compound was evaluated for the inhibition of human Acetylcholinesterase None 43.0 nM
Inhibition against Acetylcholinesterase (AChE) None 18.97 nM
Inhibitory activity against acetylcholinesterase in human erythrocytes None 17.78 nM
Inhibitory concentration against acetylcholinesterase from human erythrocytes None 17.78 nM
Inhibition of acetylcholinesterase (AChE) of human erythrocytes Homo sapiens 14.13 nM
Inhibitory activity against acetylcholinesterase None 0.68 nM
In vitro inhibitory concentration against acetylcholinesterase (AChE) obtained from mouse brain homogenate. None 0.69 nM
In vitro inhibitory effect on rat Acetylcholinesterase None 80.0 nM
Inhibitory activity against acetylcholine esterase (AChE) None 190.0 nM
Inhibitory concentration in vitro and ex vivo for anti-AChE activity in rat brain None 0.68 nM
Inhibition of rat acetylcholinesterase (AChE) None 14.0 nM
Inhibitory concentration against rat brain acetylcholinesterase AChE Rattus norvegicus 2.0 nM
In vitro inhibitory activity against acetylcholinesterase None 0.43 nM
Inhibition acetylcholinesterase (AChE) enzyme. None 57.02 nM
Compound was evaluated for its inhibitory concentration against Horse serum Butyrylcholinesterase Equus caballus 16.0 nM
In vitro inhibition of Butyrylcholinesterase from human serum None 73.0 nM
Anticholinesterase activity against plasma Butyrylcholinesterase (BChE) in humans. None 16.0 nM
In vitro inhibition of human serum Butyrylcholinesterase. None 23.1 nM
Concentration required to inhibit 50% of Butyrylcholinesterase obtained from human serum was determined in vitro None 73.0 nM
Inhibition of human Butyrylcholinesterase Homo sapiens 16.0 nM
In vitro inhibition of human plasma butyrylcholinesterase. None 16.0 nM
Inhibitory concentration against butyrylcholinesterase from human serum None 22.91 nM
Inhibition of Butyrylcholinesterase (BChE) of human erythrocytes [-log IC50 (uM)] Homo sapiens 22.91 nM
Butyrylcholinesterase None 8.1 nM
Inhibitory concentration was determined in in vitro for Butyrylcholinesterase in rat plasma None 8.1 nM
Inhibition of isolated Butyrylcholinesterase (BuChE ) Rattus norvegicus 23.0 nM
In vitro inhibition of human butryl cholinesterase. None 35.0 nM
Compound was evaluated for the in vitro inhibition of the Butyrylcholinesterase from horse serum Equus caballus 73.0 nM
Inhibitory activity against Butyrylcholinesterase in cortex Homo sapiens 129.0 nM
Inhibitory activity against Butyrylcholinesterase in plasma Homo sapiens 15.0 nM
The compound was evaluated for the inhibition human of Butyrylcholinesterase None 35.0 nM
In vitro inhibitory concentration against butyrylcholinesterase (BuChE) obtained from rat plasma None 8.1 nM
Inhibitory activity towards acetylcholine esterase (AChE) Torpedo californica 360.0 nM
Inhibitory concentration against acetylcholinesterase None 30.0 nM Inhibitory concentration against acetylcholinesterase None 0.008 ug.mL-1
Inhibitory concentration against human plasma Butyrylcholinesterase Homo sapiens 16.0 nM
Inhibitory concentration against human erythrocyte Acetylcholinesterase Homo sapiens 28.0 nM
Inhibition of human AChE induced beta-amyloid aggregation in thioflavin T-based fluorometric assay Homo sapiens 30.0 %
Anticholinesterase activity against human erythrocyte AChE Homo sapiens 28.0 nM
Anticholinesterase activity against human plasma BChE Homo sapiens 16.0 nM
Inhibition of AChE Homo sapiens 500.0 nM Inhibition of AChE Homo sapiens 493.17 nM
Inhibition of human recombinant AChE Homo sapiens 13.49 nM
Inhibition of human recombinant BChE Homo sapiens 26.3 nM
Inhibition of electric eel AChE by modified Ellman method Electrophorus electricus 41.0 nM
Inhibition of BChE None 857.0 nM
Inhibition of electric eel AChE by Ellman's method Electrophorus electricus 41.0 nM
Inhibition of horse BChE Equus caballus 857.0 nM
Inhibition of human plasma BuchE by Ellman's method Homo sapiens 28.0 nM
Inhibition of electric eel AchE by Ellman's method Electrophorus electricus 103.0 nM
Inhibition of BuChE in human liver microsomes Homo sapiens 19.0 nM
Inhibition of electric eel AChE type 6S Electrophorus electricus 53.0 nM
Inhibition of mouse brain AChE after 1 hr by modified Ellman's colorimetric method Mus musculus 40.0 nM
Inhibition of mouse serum BChE after 1 hr by modified Ellman's colorimetric method Mus musculus 280.0 nM
Inhibition of mouse brain AChE after 1 hr by modified Ellman's colorimetric method Mus musculus 40.0 nM
Inhibition of mouse serum BChE after 1 hr by modified Ellman's colorimetric method Mus musculus 280.0 nM
Inhibition of rat brain AChE by Ellman's method Rattus norvegicus 1.0 nM
Inhibition of rat plasma BChE by Ellman's method Rattus norvegicus 7.6 nM
Inhibition of electric eel AChE at 350 mM by microplate assay Electrophorus electricus 87.0 %
Inhibition of human FAAH at 1 uM Homo sapiens 18.85 % Inhibition of human FAAH at 1 uM Homo sapiens 12.37 %
Inhibition of human whole RBC AChE pretreated for 30 mins by Ellman technique Homo sapiens 27.9 nM
Inhibition of human plasma BChE pretreated for 30 mins by Ellman technique Homo sapiens 16.0 nM
Inhibition of human AChE by Ellmans test Homo sapiens 56.7 nM
DRUGMATRIX: Acetylcholinesterase enzyme inhibition (substrate: acetylthiocholine) None 175.0 nM
DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 200.0 nM
Inhibition of human erythrocyte AChE assessed as acetylthiocholine iodide hydrolysis after 10 mins preincubation by spectrophotometry Homo sapiens 150.0 nM
Inhibition of electric eel AChE using acetylthiocholine as substrate at 350 uM by Ellman's method Electrophorus electricus 94.0 %
Inhibition of AChE in Wistar rat brain homogenate using acetylthiocholine iodide as substrate after 0.5 hrs by Ellman's method Rattus norvegicus 11.0 nM
Inhibition of BuChE in Wistar rat plasma using acetylthiocholine iodide as substrate after 0.5 hrs by Ellman's method Rattus norvegicus 58.4 nM
Inhibition of Electric eel AChE using acetylthiocholine as substrate after 2 mins Electrophorus electricus 90.0 nM
Inhibition of equine serum BChE using acetylthiocholine as substrate after 2 mins Equus caballus 42.0 nM
Time dependent inhibition of Electric eel AChE assessed as stability constants of inhibitor-enzyme complex using acetylthiocholine as substrate after 60 mins Electrophorus electricus 34.0 nM
Time dependent inhibition of equine serum BChE assessed as stability constants of inhibitor-enzyme complex using acetylthiocholine as substrate after 60 mins Equus caballus 41.0 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 89.33 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 87.96 %
Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate incubated for 20 min prior to substrate addition measured after 20 min by Ellman's method Homo sapiens 0.013 ug.mL-1
Inhibition of Electrophorus electricus (electric eel) AChE using acetylthiocholine iodide as substrate incubated for 15 min prior to substrate addition measured after 30 min by Ellman's spectrophotometric method Electrophorus electricus 0.034 ug.mL-1
Inhibition of acetylcholinesterase (unknown origin) using acetylcholine iodide as substrate preincubated for 15 mins prior to substrate addition by spectrophotometric analysis Homo sapiens 2.9 nM
Inhibition of BChE (unknown origin) using butyryl thiocholine iodide as substrate after 30 mins by Ellman's method Homo sapiens 850.0 nM
Inhibition of AChE (unknown origin) using acetyl thiocholine iodide as substrate after 30 mins by Ellman's method Homo sapiens 40.0 nM
Inhibition of BChE (unknown origin) using butyryl thiocholine iodide as substrate at 0.25 mM after 30 mins by Ellman's method Homo sapiens 92.54 %
Inhibition of AChE (unknown origin) using acetyl thiocholine iodide as substrate at 0.25 mM after 30 mins by Ellman's method Homo sapiens 92.54 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 78.13 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 80.76 %
Inhibition of recombinant human AChE expressed in HEK293 cells using acetylthiocholine iodide as substrate preincubated for 5 mins before substrate addition measured after 10 mins by Ellman's method Homo sapiens 160.0 nM
Inhibition of acetylcholine esterase in chicken biventer cervicis muscle assessed as rate of acetylcholine hydrolysis by Ellman's method Gallus gallus 20.0 nM
Inhibition of equine serum BChE by Ellman's method Equus caballus 60.0 nM
Inhibition of electric eel AChE by Ellman's method Electrophorus electricus 7.7 nM
Inhibition of equine serum BChE at 10 uM by Ellman's method Equus caballus 7.22 %
Inhibition of electric eel AChE at 10 uM by Ellman's method Electrophorus electricus 8.11 %
Inhibition of BChE (unknown origin) using BCh iodide as substrate preincubated for 15 mins prior to substrate addition measured after 10 mins by Ellman's method Homo sapiens 930.0 nM
Inhibition of Pacific electric ray AChE using acetylthiocholine iodide as substrate after 60 mins by Ellman's method Torpedo californica 11.0 nM
Inhibition of BChE in horse serum using butyrylthiocholine iodide as substrate after 120 mins by Ellman's method Equus caballus 14.0 nM
Inhibition of electric eel AChE using ATC iodide substrate by DTNB based assay Electrophorus electricus 90.0 nM
Inhibition of equine serum BChE using ATC iodide substrate by DTNB based assay Equus caballus 40.0 nM
Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate at 0.5 mM preincubated for 30 mins before substrate addition measured after 30 mins by Ellman method relative to control Homo sapiens 91.27 %
Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate preincubated for 30 mins before substrate addition measured after 30 mins by Ellman method Homo sapiens 40.0 nM
Inhibition of BChE (unknown origin) using butyrylthiocholine chloride as substrate at 0.5 mM preincubated for 30 mins before substrate addition measured after 30 mins by Ellman method relative to control Homo sapiens 82.82 %
Inhibition of BChE (unknown origin) using butyrylthiocholine chloride as substrate preincubated for 30 mins before substrate addition measured after 30 mins by Ellman method Homo sapiens 850.0 nM
Inhibition of equine serum butyrylcholinesterase using butyrylcholine iodide as substrate preincubated for 30 mins followed by substrate addition measured after 2.5 mins by Ellman's spectrophotometric method Equus caballus 78.0 nM
Inhibition of human acetylcholinesterase using acetylcholine iodide as substrate preincubated for 30 mins followed by substrate addition measured after 2.5 mins by Ellman's spectrophotometric method Homo sapiens 32.0 nM
Inhibition of equine serum BChE using S-butyrylthiocholine chloride as substrate incubated for 30 mins by Ellman's microplate assay Equus caballus 220.0 nM
Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate incubated for 30 mins by Ellman's microplate assay Homo sapiens 80.0 nM
Inhibition of electric eel AChE preincubated for 15 mins followed by addition of acetylthiocholine iodide as substrate measured after 30 mins by Ellman's microplate assay Electrophorus electricus 160.0 nM
Inhibition of equine serum BChE preincubated for 15 mins followed by addition of S-butyrylthiocholine chloride as substrate measured after 30 mins by Ellman's microplate assay Equus caballus 580.0 nM
Inhibition of electric eel AChE using acetylthiocholine iodide as substrate preincubated for 10 mins followed by substrate addition measured after 30 mins by Ellman's method Electrophorus electricus 40.0 nM
Inhibition of equine serum BCHE using butyrylthiocholine iodide as substrate preincubated for 10 mins followed by substrate addition measured after 30 mins by Ellman's method Equus caballus 850.0 nM
Inhibition of electric eel AChE at 0.5 mM using acetylthiocholine iodide as substrate preincubated for 10 mins followed by substrate addition measured after 30 mins by Ellman's method relative to control Electrophorus electricus 91.27 %
Inhibition of equine serum BCHE at 0.5 mM using butyrylthiocholine iodide as substrate preincubated for 10 mins followed by substrate addition measured after 30 mins by Ellman's method relative to control Equus caballus 82.82 %
Inhibition of AChE (unknown origin) Homo sapiens 220.0 nM
Inhibition of BuChE (unknown origin) using butyrylthiocholine chloride as substrate preincubated for 15 mins followed by substrate addition measured after 30 mins by Ellman's method Homo sapiens 850.0 nM
Inhibition of Electrophorus electricus AChE using acetylthiocholine iodide as substrate preincubated for 30 mins followed by substrate addition and measured after 5 mins by Ellman's method Electrophorus electricus 3.0 nM
Inhibition of electric eel AChE at 50 uM incubated for 15 mins by Ellman's method relative to control Electrophorus electricus 99.8 %
Inhibition of equine serum BChE at 50 uM using S-butyrylthiocholine iodide as substrate incubated for 15 mins by Ellman's method relative to control Equus caballus 93.2 %
Inhibition of electric eel AChE incubated for 15 mins by Ellman's method Electrophorus electricus 7.8 nM
Inhibition of acetylcholinesterase (unknown origin) using acetylthiocholine as substrate preincubated for 30 mins followed by substrate addition and measured after 2 mins by Ellman's method Homo sapiens 538.0 nM
Inhibition of human AChE using acetylthiocholine iodide as substrate measured for 1 min by spectrophotometric based Ellman's method Homo sapiens 63.0 nM
Inhibition of human BuChE using butyrylthiocholine iodide as substrate measured for 1 min by spectrophotometric based Ellman's method Homo sapiens 130.0 nM
Inhibition of electric eel acetylcholinesterase using acetylthiocholine iodide as substrate at 10 mg/ml by Ellman's method relative to control Electrophorus electricus 98.0 %
Inhibition of human erythrocytes AChE using acetylthiocholine iodide as substrate measured after 30 mins by Ellman's method Homo sapiens 80.0 nM
Inhibition of human AChE using acetylthiocholine as substrate by Ellman's method Homo sapiens 200.0 nM
Inhibition of human BuChE at 100 uM using butyrylthiocholine chloride as substrate by Ellman's method Homo sapiens 99.9 %
Inhibition of human BuChE using butyrylthiocholine chloride as substrate by Ellman's method Homo sapiens 300.0 nM
Inhibition of AChE (unknown origin) Homo sapiens 16.0 nM
Inhibition of BuChE (unknown origin) Homo sapiens 16.0 nM

Cross References

Resources Reference
ChEBI 27953
ChEMBL CHEMBL94
DrugBank DB00981
DrugCentral 2159
FDA SRS 9U1VM840SP
Human Metabolome Database HMDB0015116
Guide to Pharmacology 6598
KEGG C06535
PharmGKB PA450957
PubChem 5983
SureChEMBL SCHEMBL24044
ZINC ZINC000091689892
CONTENTS