Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H14N2 |
| Molecular Weight | 198.2637 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=C2C=CC=CC2=NC3=C1CCCC3
InChI
InChIKey=YLJREFDVOIBQDA-UHFFFAOYSA-N
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB00382Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/cognex.html
Sources: http://www.drugbank.ca/drugs/DB00382
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/cognex.html
Tacrine is a parasympathomimetic- a reversible cholinesterase inhibitor that is indicated for the treatment of mild to moderate dementia of the Alzheimer's type. An early pathophysiological feature of Alzheimer's disease that is associated with memory loss and cognitive deficits is a deficiency of acetylcholine as a result of selective loss of cholinergic neurons in the cerebral cortex, nucleus basalis, and hippocampus. Tacrine is postulated to exert its therapeutic effect by enhancing cholinergic function. This is accomplished by increasing the concentration of acetylcholine at cholinergic synapses through reversible inhibition of its hydrolysis by acetylcholinesterase. If this proposed mechanism of action is correct, tacrine's effect may lessen as the disease progresses and fewer cholinergic neurons remain functionally intact. There is no evidence that tacrine alters the course of the underlying dementing process. The mechanism of tacrine is not fully known, but it is suggested that the drug is an anticholinesterase agent which reversibly binds with and inactivates cholinesterases. This inhibits the hydrolysis of acetylcholine released from functioning cholinergic neurons, thus leading to an accumulation of acetylcholine at cholinergic synapses. The result is a prolonged effect of acetylcholine. is used for the palliative treatment of mild to moderate dementia of the Alzheimer's type. Tacrine was marketed under the trade name Cognex. Because of its liver toxicity and attendant requirement for monitoring liver function, tacrine prescriptions dropped after other acetylcholinesterase inhibitors were introduced, and its use has been largely discontinued.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL220 Sources: http://www.drugbank.ca/drugs/DB00382 |
500.0 nM [IC50] | ||
Target ID: CHEMBL1914 Sources: http://www.drugbank.ca/drugs/DB00382 |
23.0 nM [IC50] | ||
Target ID: CHEMBL2190 |
0.46 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Cognex Approved UseCognex® (tacrine hydrochloride capsules) is indicated for the treatment of mild to moderate dementia of the Alzheimer's type. Launch Date7.474464E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7836549 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
TACRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
91.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7836549 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
TACRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7836549 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
TACRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, 71.2 years (range: 52-88 years) n = 64 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 71.2 years (range: 52-88 years) Sex: M+F Population Size: 64 Sources: |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (21 patient) Sources: Vomiting (21 patient) Anorexia (21 patient) Dyspepsia (21 patient) Diarrhea (21 patient) Abdominal pain (21 patient) |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 146 Health Status: unhealthy Age Group: adult Population Size: 146 Sources: Page: p. 5 |
Disc. AE: Transaminases increased, Atrial fibrillation... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: Page: p. 5Atrial fibrillation (1 patient) Dyspnea (1 patient) Chest pain (1 patient) |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 150 Health Status: unhealthy Age Group: adult Population Size: 150 Sources: Page: p. 5 |
Disc. AE: Transaminases increased, Nausea... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: Page: p. 5Nausea (1 patient) Vomiting (1 patient) Pallor (1 patient) Vasodilatation (1 patient) Sweating increased (1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Abdominal pain | 21 patient Disc. AE |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, 71.2 years (range: 52-88 years) n = 64 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 71.2 years (range: 52-88 years) Sex: M+F Population Size: 64 Sources: |
| Anorexia | 21 patient Disc. AE |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, 71.2 years (range: 52-88 years) n = 64 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 71.2 years (range: 52-88 years) Sex: M+F Population Size: 64 Sources: |
| Diarrhea | 21 patient Disc. AE |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, 71.2 years (range: 52-88 years) n = 64 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 71.2 years (range: 52-88 years) Sex: M+F Population Size: 64 Sources: |
| Dyspepsia | 21 patient Disc. AE |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, 71.2 years (range: 52-88 years) n = 64 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 71.2 years (range: 52-88 years) Sex: M+F Population Size: 64 Sources: |
| Nausea | 21 patient Disc. AE |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, 71.2 years (range: 52-88 years) n = 64 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 71.2 years (range: 52-88 years) Sex: M+F Population Size: 64 Sources: |
| Vomiting | 21 patient Disc. AE |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, 71.2 years (range: 52-88 years) n = 64 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 71.2 years (range: 52-88 years) Sex: M+F Population Size: 64 Sources: |
| Atrial fibrillation | 1 patient Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 146 Health Status: unhealthy Age Group: adult Population Size: 146 Sources: Page: p. 5 |
| Chest pain | 1 patient Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 146 Health Status: unhealthy Age Group: adult Population Size: 146 Sources: Page: p. 5 |
| Dyspnea | 1 patient Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 146 Health Status: unhealthy Age Group: adult Population Size: 146 Sources: Page: p. 5 |
| Transaminases increased | 1 patient Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 146 Health Status: unhealthy Age Group: adult Population Size: 146 Sources: Page: p. 5 |
| Nausea | 1 patient Disc. AE |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 150 Health Status: unhealthy Age Group: adult Population Size: 150 Sources: Page: p. 5 |
| Pallor | 1 patient Disc. AE |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 150 Health Status: unhealthy Age Group: adult Population Size: 150 Sources: Page: p. 5 |
| Sweating increased | 1 patient Disc. AE |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 150 Health Status: unhealthy Age Group: adult Population Size: 150 Sources: Page: p. 5 |
| Transaminases increased | 1 patient Disc. AE |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 150 Health Status: unhealthy Age Group: adult Population Size: 150 Sources: Page: p. 5 |
| Vasodilatation | 1 patient Disc. AE |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 150 Health Status: unhealthy Age Group: adult Population Size: 150 Sources: Page: p. 5 |
| Vomiting | 1 patient Disc. AE |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 150 Health Status: unhealthy Age Group: adult Population Size: 150 Sources: Page: p. 5 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Suxamethonium apnoea masked by tetrahydroaminacrine. | 1978 Jul-Aug |
|
| Amino acridines action on Friend's retrovirus in relation to their molecular ionization. | 1989 |
|
| Effects of four non-cholinergic cognitive enhancers in comparison with tacrine and galanthamine on scopolamine-induced amnesia in rats. | 1992 |
|
| Synthesis and cholinergic properties of bis[[(dimethylamino)methyl]furanyl] analogues of ranitidine. | 1992 Mar 20 |
|
| Antiamnesic and cholinomimetic side-effects of the cholinesterase inhibitors, physostigmine, tacrine and NIK-247 in rats. | 1993 Nov 30 |
|
| Systemic administration of lithium chloride and tacrine but not kainic acid augments citrulline content of rat brain. | 1995 Dec 27 |
|
| Adverse interaction of tacrine and haloperidol. | 1996 Nov |
|
| Nicotine and sensory memory in Alzheimer's disease: an event-related potential study. | 2002 Jul |
|
| Tacrine attenuates hydrogen peroxide-induced apoptosis by regulating expression of apoptosis-related genes in rat PC12 cells. | 2002 Oct 30 |
|
| Inhibition of human cholinesterases by drugs used to treat Alzheimer disease. | 2003 Apr-Jun |
|
| Reduction in distractibility with AF102B and THA in the macaque. | 2003 Sep |
|
| Cholinesterase inhibitors modify the activity of intrinsic cardiac neurons. | 2004 Aug |
|
| Choline pivaloyl esters improve in rats cognitive and memory performances impaired by scopolamine treatment or lesions of the nucleus basalis of Meynert. | 2004 Feb 19 |
|
| Simultaneous analysis of esterase and transferase activities in cytosol proteins from the bovine retina by using microscale non-denaturing two-dimensional electrophoresis. | 2004 Jan 14 |
|
| Disclosure of a pro-apoptotic glyceraldehyde-3-phosphate dehydrogenase promoter: anti-dementia drugs depress its activation in apoptosis. | 2004 May 14 |
|
| In vitro inactivation of rat brain acetylcholinesterase by DSP-4 and its derivatives OS-21 and OS-23 and protective activity of tacrine (9-amino-1,2,3,4-tetrahydroacridine). | 2005 |
|
| Validation of the tremulous jaw movement model for assessment of the motor effects of typical and atypical antipychotics: effects of pimozide (Orap) in rats. | 2005 Feb |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Pharmacological characterization of orally active cholinesterase inhibitory activity of Prunus persica L. Batsch in rats. | 2006 |
|
| Dopamine and adenosine receptor interaction as basis for the treatment of Parkinson's disease. | 2006 Oct 25 |
|
| Potential cognitive enhancing and disease modification effects of SSRIs for Alzheimer's disease. | 2007 |
|
| Progress update: Pharmacological treatment of Alzheimer's disease. | 2007 |
|
| Long-term tetrahydroaminoacridine treatment and quantitative EEG in Alzheimer's disease. | 2007 |
|
| Current therapeutic options for Alzheimer's disease. | 2007 Dec |
|
| Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics. | 2007 Jun |
|
| Allosteric modulation of muscarinic acetylcholine receptors. | 2007 Sep |
|
| The investigation of structure-activity relationships of tacrine analogues: electronic-topological method. | 2008 Aug 6 |
|
| NO-donating tacrine hybrid compounds improve scopolamine-induced cognition impairment and show less hepatotoxicity. | 2008 Dec 25 |
|
| 1-Phenyl-6,7,8,9-hexa-hydro-1H,5H-cyclo-hepta-[1',2':2,3]pyrido[6,5-c]pyrazol-4-amine: a new tacrine analogue. | 2008 May 10 |
|
| New performance of biosensor technology for Alzheimer's disease drugs: in vitro comparison of tacrine and 7-methoxytacrine. | 2008 Oct |
|
| The protective effect of the cholinergic anti-inflammatory pathway against septic shock in rats. | 2008 Oct |
|
| Comparative effects of cationic triarylmethane, phenoxazine and phenothiazine dyes on horse serum butyrylcholinesterase. | 2008 Oct 15 |
|
| Comparison studies of tacrine and bis7-tacrine on the suppression of scopolamine-induced behavioral changes and inhibition of acetylcholinesterase in mice. | 2009 |
|
| The 5-choice continuous performance test: evidence for a translational test of vigilance for mice. | 2009 |
|
| Rapid determination of tacrine and other drug metabolites in microsomal incubate by newly developed targeting algorithm on UHPLC/TOFMS. | 2009 Dec 15 |
|
| Once-daily transdermal rivastigmine in the treatment of Alzheimer's disease. | 2009 Feb 6 |
|
| Effects of zonisamide on c-Fos expression under conditions of tacrine-induced tremulous jaw movements in rats: a potential mechanism underlying its anti-parkinsonian tremor effect. | 2009 Jan |
|
| Determination of basic azaarenes in aviation kerosene by solid-phase extraction and HPLC-fluorescence detection. | 2009 Jun |
|
| Identification of FDA-approved drugs and bioactives that protect hair cells in the zebrafish (Danio rerio) lateral line and mouse (Mus musculus) utricle. | 2009 Jun |
|
| An integrated approach to improved toxicity prediction for the safety assessment during preclinical drug development using Hep G2 cells. | 2009 Jun 1 |
|
| Long-lasting decreases in cocaine-reinforced behavior following treatment with the cholinesterase inhibitor tacrine in rats selectively bred for drug self-administration. | 2009 Nov |
|
| Coupling an HCN2-expressing cell to a myocyte creates a two-cell pacing unit. | 2009 Nov 1 |
|
| Contribution of the d-Serine-Dependent Pathway to the Cellular Mechanisms Underlying Cognitive Aging. | 2010 |
|
| Tacrine-NO donor and tacrine-ferulic acid hybrid molecules as new anti-Alzheimer agents: hepatotoxicity and influence on the cytochrome P450 system in comparison to tacrine. | 2010 |
|
| A second-generation device for automated training and quantitative behavior analyses of molecularly-tractable model organisms. | 2010 Dec 17 |
|
| Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones. | 2010 Feb |
|
| A novel animal model to evaluate the ability of a drug delivery system to promote the passage through the BBB. | 2010 Jan 18 |
|
| Development of a highly sensitive cytotoxicity assay system for CYP3A4-mediated metabolic activation. | 2011 Aug |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
| A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. | 2014 Jan |
Sample Use Guides
Oral
Initially, 10 mg 4 times daily for at least 4 weeks.
If well tolerated and increased serum ALT concentrations have not occurred, increase dosage to 20 mg 4 times daily; if tolerated, increase dosage in 40-mg daily increments (divided into 4 doses daily) at 4-week intervals up to a maximum of 160 mg daily (40 mg 4 times daily).
Route of Administration:
Oral
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| Classification Tree | Code System | Code | ||
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WHO-ATC |
N06DA01
Created by
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NDF-RT |
N0000175723
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WHO-VATC |
QN06DA01
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NDF-RT |
N0000000177
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NCI_THESAURUS |
C47792
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LIVERTOX |
NBK547868
Created by
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DTXSID1037272
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45980
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CHEMBL95
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1935
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C61961
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M10424
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6687
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10318
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206-291-2
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SUB10796MIG
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4VX7YNB537
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4VX7YNB537
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2551
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800
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321-64-2
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D013619
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TACRINE
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DB00382
Created by
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
