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Identification
NameTacrine
Accession NumberDB00382  (APRD00690)
TypeSmall Molecule
GroupsWithdrawn
DescriptionA centerally active cholinesterase inhibitor that has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders. Tacrine has been discontinued for the United States market.
Structure
Thumb
Synonyms
1,2,3,4-tetrahydroacridin-9-amine
Tacrin
Tacrine
Tacrinum
Tetrahydroaminacrine
Tetrahydroaminoacridine
THA
External Identifiers
  • CI 970
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CognexShionogi
TalemLKM
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Tacrine Hydrochloride
ThumbNot applicableDBSALT001053
Categories
UNII4VX7YNB537
CAS number321-64-2
WeightAverage: 198.2637
Monoisotopic: 198.115698458
Chemical FormulaC13H14N2
InChI KeyInChIKey=YLJREFDVOIBQDA-UHFFFAOYSA-N
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)
IUPAC Name
1,2,3,4-tetrahydroacridin-9-amine
SMILES
NC1=C2CCCCC2=NC2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Aminoquinoline
  • Aminopyridine
  • Benzenoid
  • Pyridine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the palliative treatment of mild to moderate dementia of the Alzheimer's type.
PharmacodynamicsTacrine 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.
Mechanism of actionThe 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.
Related Articles
AbsorptionTacrine is rapidly absorbed. Absolute bioavailability of tacrine is approximately 17%.
Volume of distribution
  • 349 ± 193 L
Protein binding55%
Metabolism

Hepatic. Cytochrome P450 1A2 is the principal isozyme involved in tacrine metabolism. The major metabolite, 1-hydroxy-tacrine (velnacrine), has central cholinergic activity.

SubstrateEnzymesProduct
Tacrine
1-hydroxytacrineDetails
Route of eliminationNot Available
Half life2 to 4 hours
ClearanceNot Available
ToxicityOverdosage with cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. The estimated median lethal dose of tacrine following a single oral dose in rats is 40 mg/kg, or approximately 12 times the maximum recommended human dose of 160 mg/day.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9783
Blood Brain Barrier+0.978
Caco-2 permeable-0.5267
P-glycoprotein substrateNon-substrate0.6195
P-glycoprotein inhibitor INon-inhibitor0.9247
P-glycoprotein inhibitor IINon-inhibitor0.9103
Renal organic cation transporterNon-inhibitor0.5073
CYP450 2C9 substrateNon-substrate0.8532
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7248
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5541
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.9404
BiodegradationNot ready biodegradable0.9773
Rat acute toxicity3.4207 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9351
hERG inhibition (predictor II)Non-inhibitor0.6164
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Shionogi pharma inc
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Cognex 10 mg capsule3.03USD capsule
Cognex 20 mg capsule3.03USD capsule
Cognex 40 mg capsule3.03USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point183.5 °CPhysProp
water solubility217 mg/LNot Available
logP2.71HANSCH,C ET AL. (1995)
pKa9.95 (at 20 °C)PERRIN,DD (1972)
Predicted Properties
PropertyValueSource
Water Solubility0.136 mg/mLALOGPS
logP3.13ALOGPS
logP2.63ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)8.95ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.91 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity61.74 m3·mol-1ChemAxon
Polarizability22.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.22 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

S. Shirley Yang, Wayne Boisvert, Nouman A. Muhammad, Jay Weiss, “Controlled release tacrine drug delivery systems and methods for preparing same.” U.S. Patent US5576022, issued February, 1993.

US5576022
General References
  1. Qizilbash N, Whitehead A, Higgins J, Wilcock G, Schneider L, Farlow M: Cholinesterase inhibition for Alzheimer disease: a meta-analysis of the tacrine trials. Dementia Trialists' Collaboration. JAMA. 1998 Nov 25;280(20):1777-82. [PubMed:9842955 ]
  2. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . 2006 Jun;():. [PubMed:20480924 ]
External Links
ATC CodesN06DA01
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (19.4 KB)
Interactions
Drug Interactions
Drug
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Tacrine.
AbirateroneThe serum concentration of Tacrine can be increased when it is combined with Abiraterone.
AcebutololTacrine may increase the bradycardic activities of Acebutolol.
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Tacrine.
AcetylcholineThe risk or severity of adverse effects can be increased when Tacrine is combined with Acetylcholine.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Tacrine.
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Tacrine.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Tacrine.
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Tacrine.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Tacrine.
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Tacrine.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Tacrine.
AlprenololTacrine may increase the bradycardic activities of Alprenolol.
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Tacrine.
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Tacrine.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Tacrine.
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Tacrine.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Tacrine.
ArecolineThe risk or severity of adverse effects can be increased when Tacrine is combined with Arecoline.
ArotinololTacrine may increase the bradycardic activities of Arotinolol.
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Tacrine.
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Tacrine.
AtenololTacrine may increase the bradycardic activities of Atenolol.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Tacrine.
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Tacrine.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Tacrine.
AzithromycinThe metabolism of Tacrine can be decreased when combined with Azithromycin.
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Tacrine.
BefunololTacrine may increase the bradycardic activities of Befunolol.
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Tacrine.
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Tacrine.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Tacrine.
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Tacrine.
BetaxololTacrine may increase the bradycardic activities of Betaxolol.
BethanecholThe risk or severity of adverse effects can be increased when Tacrine is combined with Bethanechol.
BevantololTacrine may increase the bradycardic activities of Bevantolol.
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Tacrine.
BisoprololTacrine may increase the bradycardic activities of Bisoprolol.
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Tacrine.
BopindololTacrine may increase the bradycardic activities of Bopindolol.
BortezomibThe metabolism of Tacrine can be decreased when combined with Bortezomib.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Tacrine.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Tacrine.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Tacrine.
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Tacrine.
BufuralolTacrine may increase the bradycardic activities of Bufuralol.
BupranololTacrine may increase the bradycardic activities of Bupranolol.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Tacrine.
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Tacrine.
CaffeineThe metabolism of Tacrine can be decreased when combined with Caffeine.
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Tacrine.
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Tacrine.
CarbacholThe risk or severity of adverse effects can be increased when Tacrine is combined with Carbachol.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Tacrine.
CarbamazepineThe metabolism of Tacrine can be increased when combined with Carbamazepine.
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Tacrine.
CarteololTacrine may increase the bradycardic activities of Carteolol.
CarvedilolTacrine may increase the bradycardic activities of Carvedilol.
CeliprololTacrine may increase the bradycardic activities of Celiprolol.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Tacrine.
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Tacrine.
CevimelineThe risk or severity of adverse effects can be increased when Tacrine is combined with Cevimeline.
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Tacrine.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Tacrine.
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Tacrine.
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Tacrine.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Tacrine.
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Tacrine.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Tacrine.
CitalopramThe metabolism of Tacrine can be decreased when combined with Citalopram.
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Tacrine.
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Tacrine.
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Tacrine.
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Tacrine.
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Tacrine.
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Tacrine.
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Tacrine.
ClotrimazoleThe metabolism of Tacrine can be decreased when combined with Clotrimazole.
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Tacrine.
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Tacrine.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Tacrine.
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Tacrine.
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Tacrine.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Tacrine.
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Tacrine.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Tacrine.
Cyproterone acetateThe serum concentration of Tacrine can be decreased when it is combined with Cyproterone acetate.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be increased when it is combined with Tacrine.
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Tacrine.
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Tacrine.
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Tacrine.
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Tacrine.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Tacrine.
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Tacrine.
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Tacrine.
DeferasiroxThe serum concentration of Tacrine can be increased when it is combined with Deferasirox.
DehydroepiandrosteroneThe risk or severity of adverse effects can be increased when Dehydroepiandrosterone is combined with Tacrine.
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Tacrine.
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Tacrine.
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Tacrine.
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Tacrine.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Tacrine.
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Tacrine.
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Tacrine.
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Tacrine.
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Tacrine.
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Tacrine.
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Tacrine.
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Tacrine.
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Tacrine.
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Tacrine.
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Tacrine.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Tacrine.
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Tacrine.
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Tacrine.
DipyridamoleThe therapeutic efficacy of Tacrine can be decreased when used in combination with Dipyridamole.
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Tacrine.
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Tacrine.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Tacrine.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Tacrine.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Tacrine.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Tacrine.
EPIBATIDINEThe risk or severity of adverse effects can be increased when Tacrine is combined with EPIBATIDINE.
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Tacrine.
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Tacrine.
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Tacrine.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Tacrine.
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Tacrine.
EsmololTacrine may increase the bradycardic activities of Esmolol.
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Tacrine.
EstriolThe serum concentration of Estriol can be increased when it is combined with Tacrine.
EstroneThe serum concentration of Estrone can be increased when it is combined with Tacrine.
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Tacrine.
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Tacrine.
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Tacrine.
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Tacrine.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Tacrine.
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Tacrine.
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Tacrine.
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Tacrine.
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Tacrine.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Tacrine.
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Tacrine.
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Tacrine.
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Tacrine.
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Tacrine.
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Tacrine.
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Tacrine.
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Tacrine.
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Tacrine.
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Tacrine.
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Tacrine.
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Tacrine.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Tacrine.
FluvoxamineThe metabolism of Tacrine can be decreased when combined with Fluvoxamine.
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Tacrine.
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Tacrine.
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Tacrine.
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Tacrine.
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Tacrine.
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Tacrine.
GTS-21The risk or severity of adverse effects can be increased when Tacrine is combined with GTS-21.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Tacrine.
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Tacrine.
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Tacrine.
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Tacrine.
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Tacrine.
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Tacrine.
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Tacrine.
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Tacrine.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Tacrine.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Tacrine.
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Tacrine.
IndenololTacrine may increase the bradycardic activities of Indenolol.
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Tacrine.
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Tacrine.
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Tacrine.
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Tacrine.
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Tacrine.
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Tacrine.
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Tacrine.
LabetalolTacrine may increase the bradycardic activities of Labetalol.
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Tacrine.
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Tacrine.
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Tacrine.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Tacrine.
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Tacrine.
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Tacrine.
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Tacrine.
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Tacrine.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Tacrine.
LidocaineThe metabolism of Tacrine can be decreased when combined with Lidocaine.
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Tacrine.
LobelineThe risk or severity of adverse effects can be increased when Tacrine is combined with Lobeline.
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Tacrine.
LosartanThe serum concentration of Losartan can be increased when it is combined with Tacrine.
MannitolThe serum concentration of Mannitol can be increased when it is combined with Tacrine.
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Tacrine.
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Tacrine.
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Tacrine.
MethacholineThe risk or severity of adverse effects can be increased when Tacrine is combined with Methacholine.
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Tacrine.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Tacrine.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Tacrine.
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Tacrine.
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Tacrine.
MetoprololTacrine may increase the bradycardic activities of Metoprolol.
MexiletineThe metabolism of Tacrine can be decreased when combined with Mexiletine.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Tacrine.
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Tacrine.
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Tacrine.
MivacuriumTacrine may decrease the neuromuscular blocking activities of Mivacurium.
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Tacrine.
MorphineThe serum concentration of Morphine can be increased when it is combined with Tacrine.
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Tacrine.
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Tacrine.
NadololTacrine may increase the bradycardic activities of Nadolol.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Tacrine.
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Tacrine.
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Tacrine.
NevirapineThe metabolism of Tacrine can be decreased when combined with Nevirapine.
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Tacrine.
NicotineThe risk or severity of adverse effects can be increased when Tacrine is combined with Nicotine.
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Tacrine is combined with Nicotine bitartrate.
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Tacrine.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Tacrine.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Tacrine.
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Tacrine.
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Tacrine.
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Tacrine.
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Tacrine.
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Tacrine.
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Tacrine.
OsimertinibThe serum concentration of Tacrine can be decreased when it is combined with Osimertinib.
OxprenololTacrine may increase the bradycardic activities of Oxprenolol.
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Tacrine.
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Tacrine.
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Tacrine.
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Tacrine.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Tacrine.
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Tacrine.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Tacrine.
Peginterferon alfa-2bThe serum concentration of Tacrine can be increased when it is combined with Peginterferon alfa-2b.
PenbutololTacrine may increase the bradycardic activities of Penbutolol.
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Tacrine.
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Tacrine.
PhenobarbitalThe metabolism of Tacrine can be increased when combined with Phenobarbital.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Tacrine.
PilocarpineThe risk or severity of adverse effects can be increased when Tacrine is combined with Pilocarpine.
PindololTacrine may increase the bradycardic activities of Pindolol.
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Tacrine.
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Tacrine.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Tacrine.
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Tacrine.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Tacrine.
PractololTacrine may increase the bradycardic activities of Practolol.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Tacrine.
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Tacrine.
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Tacrine.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Tacrine.
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Tacrine.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Tacrine.
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Tacrine.
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Tacrine.
PrimidoneThe metabolism of Tacrine can be increased when combined with Primidone.
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Tacrine.
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Tacrine.
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Tacrine.
PropranololTacrine may increase the bradycardic activities of Propranolol.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Tacrine.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Tacrine.
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Tacrine.
QuinineThe serum concentration of Quinine can be increased when it is combined with Tacrine.
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Tacrine.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Tacrine.
RapacuroniumTacrine may decrease the neuromuscular blocking activities of Rapacuronium.
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Tacrine.
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Tacrine.
RifampicinThe metabolism of Tacrine can be increased when combined with Rifampicin.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Tacrine.
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Tacrine.
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Tacrine.
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Tacrine.
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Tacrine.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Tacrine.
RopiniroleThe metabolism of Tacrine can be decreased when combined with Ropinirole.
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Tacrine.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Tacrine.
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Tacrine.
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Tacrine.
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Tacrine.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Tacrine.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Tacrine.
SimeprevirThe metabolism of Tacrine can be decreased when combined with Simeprevir.
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Tacrine.
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Tacrine.
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Tacrine.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Tacrine.
SotalolTacrine may increase the bradycardic activities of Sotalol.
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Tacrine.
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Tacrine.
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Tacrine.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Tacrine.
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Tacrine.
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Tacrine.
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Tacrine.
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Tacrine.
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Tacrine.
TenofovirThe metabolism of Tacrine can be decreased when combined with Tenofovir.
TeriflunomideThe serum concentration of Tacrine can be decreased when it is combined with Teriflunomide.
TheophyllineThe metabolism of Tacrine can be decreased when combined with Theophylline.
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Tacrine.
TiclopidineThe metabolism of Tacrine can be decreased when combined with Ticlopidine.
TimololTacrine may increase the bradycardic activities of Timolol.
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Tacrine.
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Tacrine.
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Tacrine.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Tacrine.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Tacrine.
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Tacrine.
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Tacrine.
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Tacrine.
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Tacrine.
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Tacrine.
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Tacrine.
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Tacrine.
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Tacrine.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Tacrine.
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Tacrine.
VareniclineThe risk or severity of adverse effects can be increased when Tacrine is combined with Varenicline.
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Tacrine.
VemurafenibThe serum concentration of Tacrine can be increased when it is combined with Vemurafenib.
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Tacrine.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Tacrine.
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Tacrine.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Tacrine.
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Tacrine.
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Tacrine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Davis KL: Alzheimer's disease: seeking new ways to preserve brain function. Interview by Alice V. Luddington. Geriatrics. 1999 Feb;54(2):42-7; quiz 48. [PubMed:10024872 ]
  2. Wang H, Carlier PR, Ho WL, Wu DC, Lee NT, Li CP, Pang YP, Han YF: Effects of bis(7)-tacrine, a novel anti-Alzheimer's agent, on rat brain AChE. Neuroreport. 1999 Mar 17;10(4):789-93. [PubMed:10208549 ]
  3. Traykov L, Tavitian B, Jobert A, Boller F, Forette F, Crouzel C, Di Giamberardino L, Pappata S: In vivo PET study of cerebral [11C] methyl- tetrahydroaminoacridine distribution and kinetics in healthy human subjects. Eur J Neurol. 1999 May;6(3):273-8. [PubMed:10210906 ]
  4. Wang H, Tang XC: Anticholinesterase effects of huperzine A, E2020, and tacrine in rats. Zhongguo Yao Li Xue Bao. 1998 Jan;19(1):27-30. [PubMed:10375753 ]
  5. Kosasa T, Kuriya Y, Matsui K, Yamanishi Y: Effect of donepezil hydrochloride (E2020) on basal concentration of extracellular acetylcholine in the hippocampus of rats. Eur J Pharmacol. 1999 Sep 10;380(2-3):101-7. [PubMed:10513568 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Takatori Y: [Mechanisms of neuroprotective effects of therapeutic acetylcholinesterase inhibitors used in treatment of Alzheimer's disease]. Yakugaku Zasshi. 2006 Aug;126(8):607-16. [PubMed:16880719 ]
  8. Du DM, Carlier PR: Development of bivalent acetylcholinesterase inhibitors as potential therapeutic drugs for Alzheimer's disease. Curr Pharm Des. 2004;10(25):3141-56. [PubMed:15544504 ]
  9. Krustev AD, Argirova MD, Getova DP, Turiiski VI, Prissadova NA: Calcium-independent tacrine-induced relaxation of rat gastric corpus smooth muscles. Can J Physiol Pharmacol. 2006 Nov;84(11):1133-8. [PubMed:17218977 ]
  10. Villarroya M, Garcia AG, Marco JL: New classes of AChE inhibitors with additional pharmacological effects of interest for the treatment of Alzheimer's disease. Curr Pharm Des. 2004;10(25):3177-84. [PubMed:15544507 ]
  11. Marco JL, Carreiras MC: Recent developments in the synthesis of acetylcholinesterase inhibitors. Mini Rev Med Chem. 2003 Sep;3(6):518-24. [PubMed:12871155 ]
  12. Ahmed M, Rocha JB, Correa M, Mazzanti CM, Zanin RF, Morsch AL, Morsch VM, Schetinger MR: Inhibition of two different cholinesterases by tacrine. Chem Biol Interact. 2006 Aug 25;162(2):165-71. Epub 2006 Jun 17. [PubMed:16860785 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Wang H, Tang XC: Anticholinesterase effects of huperzine A, E2020, and tacrine in rats. Zhongguo Yao Li Xue Bao. 1998 Jan;19(1):27-30. [PubMed:10375753 ]
  2. Krustev AD, Argirova MD, Getova DP, Turiiski VI, Prissadova NA: Calcium-independent tacrine-induced relaxation of rat gastric corpus smooth muscles. Can J Physiol Pharmacol. 2006 Nov;84(11):1133-8. [PubMed:17218977 ]
  3. Marco JL, Carreiras MC: Recent developments in the synthesis of acetylcholinesterase inhibitors. Mini Rev Med Chem. 2003 Sep;3(6):518-24. [PubMed:12871155 ]
  4. Ahmed M, Rocha JB, Correa M, Mazzanti CM, Zanin RF, Morsch AL, Morsch VM, Schetinger MR: Inhibition of two different cholinesterases by tacrine. Chem Biol Interact. 2006 Aug 25;162(2):165-71. Epub 2006 Jun 17. [PubMed:16860785 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Obach RS, Reed-Hagen AE: Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos. 2002 Jul;30(7):831-7. [PubMed:12065442 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23