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Atlas / Drug / Tacrine

Tacrine

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Also known as TacrinaTacrinalTHASID11110734SID11113824SID26755281SID90341647Tacrine (THA)tetrahydroaminoacridineSID104171104SID124879172SID124879174SID144203624SID144212594SID170465420

Summary

Tacrine (CHEMBL95) is an approved small-molecule EC 3.1.1.7 (acetylcholinesterase) inhibitor (ATC N06DA01) targeting CHRM1, CHRM2, and ACHE; indicated across 2 conditions including dementia and cocaine dependence.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N06DA01
  • Targets: 4 (CHRM1, CHRM2, ACHE…)
  • Indications: 2 conditions
  • Clinical trials: 8
  • Chemistry: 198.26 Da · C13H14N2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL95
NameTacrine
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID1935
ChEBICHEBI:45980
ATCN06DA01
Molecular formulaC13H14N2
Molecular weight198.26
InChIKeyYLJREFDVOIBQDA-UHFFFAOYSA-N

SMILES: C1CCC2=NC3=CC=CC=C3C(=C2C1)N

IUPAC name: 1,2,3,4-tetrahydroacridin-9-amine

ChEBI definition: A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer’s disease.

Pharmacological roles (ChEBI): EC 3.1.1.7 (acetylcholinesterase) inhibitor.

Also known as: Tacrina, Tacrinal, Tacrine, tacrine, THA, SID11110734, SID11113824, SID26755281, SID90341647, Tacrine (THA), tetrahydroaminoacridine, SID104171104

Parent form; salt/anhydrous children: CHEMBL1677, CHEMBL1337960, CHEMBL6170062

Patent coverage: 9,855 distinct patent families (35,360 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 35,182 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CHRM1M1 receptorNegative5.70.2%P11229
CHRM2M2 receptorNegative5.680%P08172
ACHEacetylcholinesterase (Yt blood group)Inhibition7.59.6%P22303
BCHEbutyrylcholinesteraseInhibition7.20.1%P06276

Broader ChEMBL bioactivity targets: 56 (assay-derived). Sample: Lysine-specific demethylase 4E, Nuclear receptor ROR-gamma, Solute carrier family 22 member 2, Multidrug and toxin extrusion protein 1, ATP-binding cassette sub-family C member 4, Alpha-2A adrenergic receptor, Glutamate NMDA receptor; GRIN1/GRIN2B, Glutamate NMDA receptor; GRIN1/GRIN2A, Muscarinic acetylcholine receptor, Cholinesterase.

Bioactivity

ChEMBL activities: 787 potent at pChembl ≥ 5 of 834 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
BCHE10.57IC500.03nMCHEMBL_ACT_6310259
P327389.82Ki0.15nMCHEMBL_ACT_133995
BCHE9.05IC500.9nMCHEMBL_ACT_122888
P819088.92IC501.2nMCHEMBL_ACT_16800979
P819088.81IC501.53nMCHEMBL_ACT_19140502
O422758.73IC501.87nMCHEMBL_ACT_24869269
P819088.72IC501.9nMCHEMBL_ACT_25523603
P819088.7IC502nMCHEMBL_ACT_15169054
P819088.7IC502nMCHEMBL_ACT_15219522
O422758.7IC502nMCHEMBL_ACT_16513339
P819088.7IC502nMCHEMBL_ACT_16831072
P819088.7IC502nMCHEMBL_ACT_16850308
P819088.7IC502nMCHEMBL_ACT_19411123
P819088.7IC502nMCHEMBL_ACT_23250667
P819088.61IC502.43nMCHEMBL_ACT_14531382
P819088.57IC502.69nMCHEMBL_ACT_18718815
BCHE8.52IC503nMCHEMBL_ACT_25580668
P819088.52IC503nMCHEMBL_ACT_26116143
ACHE8.5IC503.16nMCHEMBL_ACT_6310255
P819088.49IC503.2nMCHEMBL_ACT_12185055
P819088.49IC503.2nMCHEMBL_ACT_18061001
P819088.49IC503.2nMCHEMBL_ACT_18385738
P819088.48IC503.3nMCHEMBL_ACT_14593920
P819088.44IC503.66nMCHEMBL_ACT_15016799
P819088.43IC503.7nMCHEMBL_ACT_15012389
P819088.42IC503.8nMCHEMBL_ACT_10898304
P819088.42IC503.8nMCHEMBL_ACT_12070526
P819088.41IC503.9nMCHEMBL_ACT_26034571
P819088.4IC504nMCHEMBL_ACT_14746351
P819088.4IC504nMCHEMBL_ACT_15042285

Target pathways

Aggregated over 4 target gene(s): CHRM1, CHRM2, ACHE, BCHE.

Top Reactome pathways

25 total, by targets touching each:

PathwayTargetsGenes
Neurotransmitter clearance2ACHE, BCHE
Synthesis of PC2ACHE, BCHE
Signal Transduction2CHRM1, CHRM2
Signaling by GPCR2CHRM1, CHRM2
Class A/1 (Rhodopsin-like receptors)2CHRM1, CHRM2
Amine ligand-binding receptors2CHRM1, CHRM2
GPCR downstream signalling2CHRM1, CHRM2
Muscarinic acetylcholine receptors2CHRM1, CHRM2
Synthesis, secretion, and deacylation of Ghrelin2ACHE, BCHE
GPCR ligand binding2CHRM1, CHRM2
Transmission across Chemical Synapses1ACHE
Neuronal System1ACHE
Metabolism1ACHE
Glycerophospholipid biosynthesis1ACHE
Phospholipid metabolism1ACHE
Membrane Trafficking1CHRM2
Peptide hormone metabolism1ACHE
Metabolism of proteins1ACHE
G alpha (q) signalling events1CHRM1
G alpha (i) signalling events1CHRM2
Metabolism of lipids1ACHE
Vesicle-mediated transport1CHRM2
Cargo recognition for clathrin-mediated endocytosis1CHRM2
Clathrin-mediated endocytosis1CHRM2
Aspirin ADME1BCHE

Dominant GO biological processes

GO termTargets
nervous system development3
signal transduction2
G protein-coupled receptor signaling pathway2
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger2
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway2
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathway2
G protein-coupled acetylcholine receptor signaling pathway2
chemical synaptic transmission2
acetylcholine receptor signaling pathway2
acetylcholine catabolic process2
phospholipase C-activating G protein-coupled receptor signaling pathway1
neuromuscular synaptic transmission1
regulation of locomotion1
positive regulation of monoatomic ion transport1
saliva secretion1

Indications & clinical

Indications

2 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
dementia4MONDO:0001627HP:0000726
cocaine dependence2MONDO:0005186EFO:0002610

Clinical trials

Total trials: 8.

Phase distribution

PhaseTrials
Not specified5
PHASE42
PHASE21

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02405104PHASE4COMPLETEDChlorzoxazone in Hip and Knee Arthroplasty
NCT04516239PHASE4COMPLETEDComparison of Metal on Metal Total Hip Arthroplasty and Metal on Metal Total Hip Resurfacing.
NCT01406522PHASE2WITHDRAWNTacrine Effects on Cocaine Self-Administration and Pharmacokinetics
NCT00374946Not specifiedCOMPLETEDA Clinical Evaluation of Wear Couples in THA
NCT03859791Not specifiedUNKNOWNTrue Incidence of Hip Dislocation After Primary THA - a Nationwide Population Study
NCT04070989Not specifiedTERMINATEDPinnacle RSA Study
NCT04637958Not specifiedCOMPLETEDCorrelation Between Femoral Head and Cup Size and Postoperative Pain in Total Hip Arthroplasty
NCT05892523Not specifiedUNKNOWNInfluence of Spinal Deformity on THA

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

617 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DONEPEZILChEMBLPhase 4 (approved)ACHE, BCHE, CHRM1, CHRM2
ETHOPROPAZINEChEMBLPhase 4 (approved)ACHE, BCHE, CHRM1, CHRM2
chenodiolChEMBL + PubChemPhase 4 (approved)ACHE, CHRM1, CHRM2
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)ACHE, CHRM1, CHRM2
PIMAVANSERINChEMBL + PubChemPhase 4 (approved)ACHE, CHRM1, CHRM2
TadalafilChEMBL + PubChemPhase 4 (approved)ACHE, CHRM1, CHRM2
VORAPAXARChEMBL + PubChemPhase 4 (approved)ACHE, CHRM1, CHRM2
ARIPIPRAZOLEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
BROMOCRIPTINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
CITALOPRAMChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
CLOTRIMAZOLEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
DEQUALINIUMChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
EBASTINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
ECONAZOLEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
EPIRUBICINChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
FLAVOXATEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
FLUOXETINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
GALLAMINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
HEXAFLUORENIUMChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
ILOPERIDONEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
MELPHALANChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
MICONAZOLEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
NICERGOLINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
OXICONAZOLEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
PALBOCICLIBChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
PERICIAZINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
QUINACRINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
RANITIDINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
RISPERIDONEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
SERTACONAZOLEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
SUNITINIBChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
TERCONAZOLEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
TRIMETREXATEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
XANOMELINEChEMBLPhase 4 (approved)ACHE, CHRM1, CHRM2
BISANTRENEChEMBLPhase 3ACHE, CHRM1, CHRM2
CETYLPYRIDINIUMChEMBLPhase 3ACHE, CHRM1, CHRM2
DROTAVERINEChEMBLPhase 3ACHE, CHRM1, CHRM2
QUERCETINChEMBLPhase 3ACHE, BCHE, CHRM2
AMINACRINEChEMBLPhase 2ACHE, CHRM1, CHRM2
BENZETHONIUMChEMBLPhase 2ACHE, CHRM1, CHRM2
BENZETHONIUM CHLORIDEChEMBLPhase 2ACHE, CHRM1, CHRM2
METERGOLINEChEMBLPhase 2ACHE, CHRM1, CHRM2
SETASTINEChEMBLPhase 2ACHE, CHRM1, CHRM2
THIOPROPERAZINEChEMBLPhase 2ACHE, CHRM1, CHRM2
ZOTEPINEChEMBLPhase 2ACHE, CHRM1, CHRM2
BinimetinibPubChemApprovedACHE, CHRM1, CHRM2
EchothiophatePubChemApprovedACHE, CHRM1, CHRM2
ImipenemPubChemApprovedACHE, CHRM1, CHRM2
levocarnitinePubChemApprovedACHE, CHRM1, CHRM2
PerindoprilPubChemApprovedACHE, CHRM1, CHRM2
podofiloxPubChemApprovedACHE, CHRM1, CHRM2
Propylene GlycolPubChemApprovedACHE, CHRM1, CHRM2
PyrazinamidePubChemApprovedACHE, CHRM1, CHRM2
PyridoxinePubChemApprovedACHE, CHRM1, CHRM2
QuinaprilatPubChemApprovedACHE, CHRM1, CHRM2
AfatinibChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2
LINAGLIPTINChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2
MavorixaforChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2
ACETYLCHOLINEChEMBLPhase 4 (approved)CHRM1, CHRM2

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot