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Compound Detail

CHEMBL1677

TACRINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.Nc1c2c(nc3ccccc13)CCCC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1677
Name TACRINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key ZUFVXZVXEJHHBN-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL95
Active Moiety CHEMBL95

Known Names

Alzyme CI-970 Cognex NSC-72108 Tacrine hcl Tacrine hydrochloride
10
Targets
37
Activities
3
Assay Types
23
PK Parameters
20
Publications
6
Known Names
1
Mechanisms

Molecular Properties

198.3
MW (Da)
2.70
ALogP
2
HBA
1
HBD
38.9
PSA (Ų)
0.71
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral
USAN Stem -crine
USAN Year 1988

Extended Properties

Molecular Formula C13H15ClN2
MW 234.73
Aromatic Rings 2
Heavy Atoms 15
NP-Likeness -0.67

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cholinesterases; ACHE & BCHE inhibitor INHIBITOR Cholinesterases; ACHE & BCHE ✓ ✓

Activity Summary

IC50 34 meas. best 8.07
Ki 2 meas. best 7.0
EC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.07 7.805 8.4 2
Cholinesterase
CHEMBL5763
 IC50 7.97 7.77 10.6 2
Butyrylcholinesterase
CHEMBL5077
 IC50 7.72 7.72 19.0 1
Cholinesterase
CHEMBL1914
 IC50 7.64 7.424 23.0 5
Acetylcholinesterase
CHEMBL4078
 IC50 7.37 7.135 42.3 4
Butyrylcholinesterase
CHEMBL3403
 IC50 7.04 7.04 92.0 1
Acetylcholinesterase
CHEMBL220
 IC50 7.03 6.6325 93.0 8
Acetylcholinesterase
CHEMBL220
 Ki 7.0 6.825 101.0 2
Acetylcholinesterase
CHEMBL4768
 IC50 6.89 6.89 130.0 3
Acetylcholinesterase
CHEMBL3199
 IC50 6.65 6.65 223.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.3 5.0571 5011.9 7

Pharmacokinetic Data

Parameter Value Units Species
AUC 176.46 ng.hr.mL-1 Rattus norvegicus
AUC 138.79 ng.hr.mL-1 Rattus norvegicus
CL 40.33 mL.min-1.kg-1 Homo sapiens
CL 77.0 mL.min-1.kg-1 Rattus norvegicus
CL 93.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 310.0 nM Rattus norvegicus
Cmax 740.0 nM Rattus norvegicus
Cmax 360.0 nM Rattus norvegicus
Cmax 700.0 nM Rattus norvegicus
F 17.0 % Homo sapiens
F 29.0 % Rattus norvegicus
F 27.0 % Rattus norvegicus
MRT 1.1 hr Rattus norvegicus
MRT 0.9 hr Rattus norvegicus
T1/2 2.0 hr Homo sapiens
T1/2 1.1 hr Rattus norvegicus
T1/2 0.9 hr Rattus norvegicus
Tmax 1.0 hr Homo sapiens
Tmax 0.5 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus
Vd 5.02 L.kg-1 Homo sapiens
Vd 5.2 L.kg-1 Rattus norvegicus
Vd 5.1 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 8.45 nM 8.07 Inhibition of equine butyrylcholinesterase using butyrylthiocholine iodide as su... 30771604
Cholinesterase IC50 = 10.6 nM 7.97 Inhibition of equine serum BuChE using butyrylthiocholine iodide as substrate af... 22512543
Butyrylcholinesterase IC50 = 19.0 nM 7.72 Inhibition of equine BChE incubated with compounf for 5 mins before addition of ... 21429752
Cholinesterase IC50 = 23.0 nM 7.64 Inhibition of human plasmatic BChE using butylthiocholne substrate preincubated ... 22818849
Cholinesterase IC50 = 27.1 nM 7.57 Inhibition of equine serum BuChE assessed as inhibition of butyrylthiocholine ch... 21497959
Unchecked IC50 = 28.9 nM 7.54 Inhibition of human butyrylcholinesterase 17944454
Cholinesterase IC50 = 40.0 nM 7.4 Inhibition of human BuChE using S-butyrylthiocholine iodide as substrate preincu... 27951490
Acetylcholinesterase IC50 = 42.3 nM 7.37 Inhibition of Electrophorus electricus Acetylcholinesterase 17944454
Cholinesterase IC50 = 43.9 nM 7.36 Inhibition of human serum BChE by Ellman's assay 18517184
Cholinesterase IC50 = 43.9 nM 7.36 Inhibitory concentration against Butyrylcholinesterase from human erythrocytes 15771413
Cholinesterase IC50 = 44.0 nM 7.36 In vitro inhibitory concentration against BChE of human serum 11741490
Acetylcholinesterase IC50 = 50.0 nM 7.3 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate by s... 21939219
Acetylcholinesterase IC50 = 69.8 nM 7.16 Inhibition of eel AChE using acetylthiocholine iodide as substrate after 5 mins ... 22512543
Butyrylcholinesterase IC50 = 92.0 nM 7.04 Inhibition of rat serum butyrylcholinesterase, in the presence of a specific ACh... 10514292
Acetylcholinesterase IC50 = 93.0 nM 7.03 Inhibition of human AChE incubated with compounf for 5 mins before addition of s... 21429752
Acetylcholinesterase Ki = 101.0 nM 7.0 Inhibition of human recombinant AChE assessed as dissociation constant for enzym... 22818849
Acetylcholinesterase IC50 = 130.0 nM 6.89 In vitro inhibitory concentration against bovine acetylcholinesterase enzyme 11741490
Acetylcholinesterase IC50 = 130.0 nM 6.89 Inhibitory concentration against Acetylcholinesterase from bovine erythrocytes 15771413
Acetylcholinesterase IC50 = 130.0 nM 6.89 Inhibition of bovine erythrocyte AChE by Ellman's assay 18517184
Acetylcholinesterase IC50 = 136.0 nM 6.87 Inhibition of human Acetylcholinesterase 17944454

Literature References

PubMed DOI Target Context # Activities
21148081 10.1124/dmd.110.035964 Rattus norvegicus 32
22512543 10.1021/jm300106z Mus musculus 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
21148081 10.1124/dmd.110.035964 Blood 6
29466774 10.1016/j.ejmech.2018.01.028 Mus musculus 6
21148081 10.1124/dmd.110.035964 Homo sapiens 5
18517184 10.1021/jm8001313 Acetylcholinesterase 4
11741490 10.1021/jm010949b Acetylcholinesterase 3
22818849 10.1016/j.ejmech.2012.06.051 Acetylcholinesterase 3
17944454 10.1021/jm070859s Acetylcholinesterase 3
20014752 10.1021/tx900326k Hepatotoxicity 3
21939219 10.1021/np200308j Acetylcholinesterase 2
10514292 10.1021/jm990224w Acetylcholinesterase 2
21148081 10.1124/dmd.110.035964 Butyrylcholinesterase 2
21148081 10.1124/dmd.110.035964 Unchecked 2
17944454 10.1021/jm070859s Unchecked 2
15771413 10.1021/jm0496741 Acetylcholinesterase 2
21148081 10.1124/dmd.110.035964 ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine