Tacrine
Tacrine (tetrahydroaminoacridine, THA) is a first-generation reversible acetylcholinesterase inhibitor used historically for symptomatic treatment of mild-to-moderate Alzheimer's disease, acting by inhibiting both acetylcholinesterase (AChE) and butyrylcholinesterase to increase acetylcholine levels in cholinergic synapses in the cortex and hippocampus. It also has additional activities including NMDA receptor antagonism, potassium channel blockade, and monoamine oxidase inhibition. Due to high hepatotoxicity risk and the availability of better-tolerated cholinesterase inhibitors, it has been largely discontinued.
Molecular Weight
198.2600 g/mol
LogP
2.70
TPSA
38.90 Ų
Lipinski RO5
Pass
Therapeutic Areas
Mechanism of Action
Inhibits acetylcholinesterase, the enzyme that hydrolyzes acetylcholine in the synaptic cleft. This increases acetylcholine availability at cholinergic synapses, enhancing cholinergic neurotransmission.
Pharmacokinetics (PK)
Pharmacodynamics (PD)
Inhibits acetylcholinesterase, the enzyme that hydrolyzes acetylcholine in the synaptic cleft. This increases acetylcholine availability at cholinergic synapses, enhancing cholinergic neurotransmission.
2D Structure
Cite this structure
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SMILES
Nc1c2c(nc3ccccc13)CCCC2
InChI
InChI=1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15)
Molecular Formula
C13H14N2
HBD / HBA
1 / 2
Rotatable Bonds
0
Heavy Atoms
15
No targets recorded
Target interaction data is not yet available for this drug.
No interactions recorded
Drug interaction data is not yet available for this compound.
No side effects recorded
Side effect data is not yet available for this drug.
Frequently Asked Questions
Tacrine (tetrahydroaminoacridine, THA) is a first-generation reversible acetylcholinesterase inhibitor used historically for symptomatic treatment of mild-to-moderate Alzheimer's disease, acting by inhibiting both acetylcholinesterase (AChE) and butyrylcholinesterase to increase acetylcholine levels in cholinergic synapses in the cortex and hippocampus. It also has additional activities including NMDA receptor antagonism, potassium channel blockade, and monoamine oxidase inhibition. Due to high hepatotoxicity risk and the availability of better-tolerated cholinesterase inhibitors, it has been largely discontinued.
Inhibits acetylcholinesterase, the enzyme that hydrolyzes acetylcholine in the synaptic cleft. This increases acetylcholine availability at cholinergic synapses, enhancing cholinergic neurotransmission.
Yes, Tacrine is an approved drug. It has reached clinical phase 4. It is classified as a Small molecule.
References & Data Sources
- ChEMBL — European Bioinformatics Institute (EBI). CHEMBL95. Open-access bioactivity database.
- PubChem — National Center for Biotechnology Information (NCBI). CID 1935. Chemical information database.
Data aggregated from publicly available pharmacological databases. Last updated 2026-03-28.
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