Compound Detail

CHEMBL94

PHYSOSTIGMINE

🧪 Phase III

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🧪 Phase III

CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN(C)[C@@H]1N2C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL94
Name	PHYSOSTIGMINE
Phase	Phase III
Structure Type	MOL
InChI Key	PIJVFDBKTWXHHD-HIFRSBDPSA-N
Therapeutic	✓ Yes

Known Names

(-)-physostigmine Cogmine Eserin Eserinum MCV-4484 NSC-30782 Physostigmine

Targets

163

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

275.4

MW (Da)

1.77

ALogP

HBA

HBD

44.8

PSA (Å²)

0.85

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-stigmine

Extended Properties

Molecular Formula	C15H21N3O2
MW	275.35
Aromatic Rings	1
Heavy Atoms	20
NP-Likeness	1.15

Indications

Glaucoma Delirium Pain Insulin Resistance

ATC Classification

S01EB05

physostigmine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

V03AB19

physostigmine

Level 1: VARIOUS

Level 2: ALL OTHER THERAPEUTIC PRODUCTS

Activity Summary

IC50 159 meas. best 9.37

Ki 4 meas. best 7.47

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Acetylcholinesterase CHEMBL220	IC50	9.37	7.1608	0.4	53
Acetylcholinesterase CHEMBL3198	IC50	9.17	8.2825	0.7	4
Acetylcholinesterase CHEMBL3199	IC50	9.17	8.0714	0.7	7
Acetylcholinesterase CHEMBL4078	IC50	9.0	7.1389	1.0	18
Butyrylcholinesterase CHEMBL3403	IC50	8.12	7.8767	7.6	6
Acetylcholinesterase CHEMBL4780	IC50	7.96	7.65	11.0	2
Cholinesterase CHEMBL5763	IC50	7.85	6.787	14.0	10
Cholinesterase CHEMBL1914	IC50	7.82	6.9209	15.0	34
Butyrylcholinesterase CHEMBL5077	IC50	7.8	6.425	16.0	4
Acetylcholinesterase CHEMBL3227914	IC50	7.7	7.7	20.0	1
Acetylcholinesterase CHEMBL4768	IC50	7.52	6.715	30.0	4
Acetylcholinesterase CHEMBL4078	Ki	7.47	6.735	34.0	2
Cholinesterase CHEMBL5763	Ki	7.39	7.39	41.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.7	6.7	200.0	1
Cholinesterase CHEMBL2528	IC50	6.55	6.55	280.0	2
Unchecked CHEMBL612545	IC50	6.44	6.44	360.0	1
Plasmodium falciparum CHEMBL364	IC50	5.4	5.3333	3981.1	6
Cholinesterase CHEMBL1914	Ki	5.3	5.3	5000.0	1
Muscarinic acetylcholine receptor M1 CHEMBL3733	IC50	4.43	4.43	37000.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	5.5	mL.min-1.kg-1	Homo sapiens
CL	22.0	mL.min-1.kg-1	Homo sapiens
F	6.0	%	Homo sapiens
T1/2	1.0	hr	-
T1/2	0.5	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Acetylcholinesterase	IC50	=	0.43	nM	9.37	In vitro inhibitory activity against acetylcholinesterase	1738151
Acetylcholinesterase	IC50	=	0.68	nM	9.17	Inhibitory activity against acetylcholinesterase	7490731
Acetylcholinesterase	IC50	=	0.68	nM	9.17	Inhibitory concentration in vitro and ex vivo for anti-AChE activity in rat brai...	-
Acetylcholinesterase	IC50	=	0.69	nM	9.16	In vitro inhibitory concentration against acetylcholinesterase (AChE) obtained f...	1469686
Acetylcholinesterase	IC50	=	1.0	nM	9.0	Inhibitory activity against acetylcholinesterase as a prodrug was demonstarted	-
Acetylcholinesterase	IC50	=	1.0	nM	9.0	Inhibition of rat brain AChE by Ellman's method	20144867
Acetylcholinesterase	IC50	=	2.0	nM	8.7	Inhibitory concentration against rat brain acetylcholinesterase AChE	9767635
Acetylcholinesterase	IC50	=	2.9	nM	8.54	Inhibition of acetylcholinesterase (unknown origin) using acetylcholine iodide a...	23746477
Acetylcholinesterase	IC50	=	3.0	nM	8.52	Inhibition of Electrophorus electricus AChE using acetylthiocholine iodide as su...	31429569
Butyrylcholinesterase	IC50	=	7.6	nM	8.12	Inhibition of rat plasma BChE by Ellman's method	20144867
Acetylcholinesterase	IC50	=	7.8	nM	8.11	Inhibition of electric eel AChE incubated for 15 mins by Ellman's method	31433188
Acetylcholinesterase	IC50	=	7.7	nM	8.11	Inhibition of electric eel AChE by Ellman's method	24819955
Butyrylcholinesterase	IC50	=	8.1	nM	8.09	Butyrylcholinesterase	7490731
Butyrylcholinesterase	IC50	=	8.1	nM	8.09	In vitro inhibitory concentration against butyrylcholinesterase (BuChE) obtained...	1469686
Butyrylcholinesterase	IC50	=	8.1	nM	8.09	Inhibitory concentration was determined in in vitro for Butyrylcholinesterase in...	-
Acetylcholinesterase	IC50	=	11.0	nM	7.96	Inhibition of AChE in Wistar rat brain homogenate using acetylthiocholine iodide...	22831800
Acetylcholinesterase	IC50	=	11.0	nM	7.96	Inhibition of Pacific electric ray AChE using acetylthiocholine iodide as substr...	24835788
Acetylcholinesterase	IC50	=	13.49	nM	7.87	Inhibition of human recombinant AChE	15588084
Acetylcholinesterase	IC50	=	14.0	nM	7.85	Inhibition of rat acetylcholinesterase (AChE)	9767635
Cholinesterase	IC50	=	14.0	nM	7.85	Inhibition of BChE in horse serum using butyrylthiocholine iodide as substrate a...	24835788

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	152
20070106	10.1021/jm901371v	Homo sapiens	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	6
2202827	10.1021/jm00171a001	Acetylcholinesterase	6
9871563	10.1016/s0960-894x(98)00076-6	Acetylcholinesterase	5
8126709	10.1021/jm00031a019	Rattus norvegicus	5
26886849	10.1021/acs.jmedchem.5b01674	Cholinesterase	5
8027982	10.1021/jm00039a013	Mus musculus	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	4
2202827	10.1021/jm00171a001	Cholinesterase	4
25059502	10.1016/j.bmc.2014.06.010	Acetylcholinesterase	3
2033583	10.1021/jm00109a009	Mus musculus	3
8126709	10.1021/jm00031a019	Mus musculus	3
8126709	10.1021/jm00031a019	Acetylcholinesterase	3
7265121	10.1021/jm00135a020	Mus musculus	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
10377231	10.1021/jm9910223	Rattus norvegicus	3
25059502	10.1016/j.bmc.2014.06.010	Cholinesterase	3
11141093	10.1021/jm000991r	Acetylcholinesterase	3
11689067	10.1021/jm010914b	ADMET	3

Data from ChEMBL 36 via Core Engine