Tacrine
Tacrine is a cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine 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 therapy is associated with a very high rate of serum aminotransferase elevations during therapy and has been linked to several instances of clinically apparent, acute liver injury. || C13H14N2 * HCl MW 234.71 CAS 1684-40-8 || Treatment of Alzheimer Disease, trademark is cognex. Reversible inhibitor of both AChE and BChE Tacrine is an oral acetylcholinesterase inhibitor previously used for therapy of Alzheimer disease. Tacrine therapy is associated with a very high rate of serum aminotransferase elevations during therapy and has been linked to several instances of clinically apparent, acute liver injury. release of endogenous 5-hydroxytryptamine (5-HT) not through a cholinergic, reserpine- or amphetamine-like mechanism or through inhibition of reuptake. The release may occur via blockade of 4-AP-insensitive K+ channels
General
Type : Derivative of Tacrine, Acridine
Chemical_Nomenclature : 1,2,3,4-tetrahydroacridin-9-amine
Canonical SMILES : C1CCC2=NC3=CC=CC=C3C(=C2C1)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)
InChIKey : YLJREFDVOIBQDA-UHFFFAOYSA-N
Other name(s) : 1,2,3,4,-tetrahydro-9 aminoacridine, Tetrahydroaminacrine, Tetrahydroaminoacridine, Cognex, tetrahydroamino-acridine, THA
MW : 198.27
Formula : C13H14N2
CAS_number : 321-64-2
PubChem : 1935
UniChem : YLJREFDVOIBQDA-UHFFFAOYSA-N
IUPHAR : 6687
Target
Families : Tacrine ligand of proteins in family
ACHE
Protein :
torca-ACHE
human-BCHE
human-CES1
human-ACHE
References (71)
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| Gene_locus related to this paper: human-ACHE |
| Title : Inhibition of human carboxylesterases hCE1 and hiCE by cholinesterase inhibitors - Tsurkan_2013_Chem.Biol.Interact_203_226 |
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| PubMedID: 23123248 |
| Title : Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition - Bencharit_2003_Chem.Biol_10_341 |
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| PubMedID: 12725862 |
| Gene_locus related to this paper: human-CES1 |
| Title : Huprine X is a Novel High-Affinity Inhibitor of Acetylcholinesterase That Is of Interest for Treatment of Alzheimer's Disease - Camps_2000_Mol.Pharmacol_57_409 |
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| PubMedID: 10648652 |
| Title : Kinetic analysis of the toxicological effect of tacrine (Cognex) on human retinal acetylcholinesterase activity - Alhomida_2000_Toxicology_147_33 |
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| PubMedID: 10837930 |
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| PubMedID: 10482456 |
| Title : Combining tacrine with milameline reverses a scopolamine-induced impairment of continuous performance in rhesus monkeys - Callahan_1999_Psychopharmacology.(Berl)_144_234 |
| Author(s) : Callahan MJ |
| Ref : Psychopharmacology (Berl) , 144 :234 , 1999 |
| PubMedID: 10435389 |
| Title : In vivo PET study of cerebral [11C] methyl- tetrahydroaminoacridine distribution and kinetics in healthy human subjects - Traykov_1999_Eur.J.Neurol_6_273 |
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| Ref : Eur Journal of Neurology , 6 :273 , 1999 |
| PubMedID: 10210906 |
| Title : Tetrahydroaminoacridine improves the recency effect in Alzheimer's disease - Riekkinen_1998_Neurosci_83_471 |
| Author(s) : Riekkinen M , Soininen H , Riekkinen P, Sr. , Kuikka J , Laakso M , Helkala EL , Partanen J , Riekkinen P, Jr. |
| Ref : Neuroscience , 83 :471 , 1998 |
| PubMedID: 9460755 |
| Title : Penetration of tacrine into cerebrospinal fluid in patients with Alzheimer's disease - Grothe_1998_J.Clin.Psychopharmacol_18_78 |
| Author(s) : Grothe DR , Piscitelli SC , Dukoff R , Fullerton T , Sunderland T , Molchan SE |
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| PubMedID: 9472847 |
| Title : Functional and subcellular organelle changes in isolated rat and human hepatocytes induced by tetrahydroaminoacridine - Monteith_1998_Arch.Toxicol_72_147 |
| Author(s) : Monteith DK , Theiss JC , Haskins JR , de la Iglesia FA |
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| PubMedID: 9520138 |
| Title : Neuroprotective effects of 2,4-dimethoxybenzylidene anabaseine (DMXB) and tetrahydroaminoacridine (THA) in neocortices of nucleus basalis lesioned rats - Meyer_1998_Brain.Res_786_252 |
| Author(s) : Meyer EM , King MA , Meyers C |
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| PubMedID: 9555043 |
| Title : Sensitivity of bovine retinal acetylcholinesterase (E.C. 3.1.1.7) toward tacrine: kinetic characterization - al-Jafari_1998_J.Biochem.Mol.Toxicol_12_245 |
| Author(s) : Al-Jafari AA , Kamal MA , Alhomida AS |
| Ref : J Biochem Mol Toxicol , 12 :245 , 1998 |
| PubMedID: 9580877 |
| Title : Responses induced by tacrine in neuronal and non-neuronal cell lines - De Ferrari_1998_J.Neurosci.Res_52_435 |
| Author(s) : De Ferrari GV , Von Bernhardi R , Calderon FH , Luza SC , Inestrosa NC |
| Ref : Journal of Neuroscience Research , 52 :435 , 1998 |
| PubMedID: 9589388 |
| Title : Shuttle-box avoidance learning in mice: improvement by combined glucose and tacrine - Pavone_1998_Neurobiol.Learn.Mem_69_204 |
| Author(s) : Pavone F , Capone F , Battaglia M , Sansone M |
| Ref : Neurobiol Learn Mem , 69 :204 , 1998 |
| PubMedID: 9619996 |
| Title : Tetrahydroaminoacridine, a cholinesterase inhibitor, and D-cycloserine, a partial NMDA receptor-associated glycine site agonist, enhances acquisition of spatial navigation - Riekkinen_1998_Neuroreport_9_1633 |
| Author(s) : Riekkinen P, Jr. , Ikonen S , Riekkinen M |
| Ref : Neuroreport , 9 :1633 , 1998 |
| PubMedID: 9631478 |
| Title : Central cardiovascular effects of tacrine in the conscious dog: a role for catecholamines and vasopressin release - Allal_1998_Eur.J.Pharmacol_348_191 |
| Author(s) : Allal C , Lazartigues E , Tran MA , Brefel-Courbon C , Gharib C , Montastruc JL , Rascol O |
| Ref : European Journal of Pharmacology , 348 :191 , 1998 |
| PubMedID: 9652334 |
| Title : Effects of AF102B and tacrine on delayed match-to-sample in monkeys - O'Neill_1998_Prog.Neuropsychopharmacol.Biol.Psychiatry_22_665 |
| Author(s) : O'Neill J , Fitten LJ , Siembieda D , Halgren E , Kim E , Fisher A , Perryman K |
| Ref : Prog Neuropsychopharmacol Biological Psychiatry , 22 :665 , 1998 |
| PubMedID: 9682279 |
| Title : Effect of subchronic treatment with metrifonate and tacrine on brain cholinergic function in aged F344 rats - Giovannini_1998_Eur.J.Pharmacol_354_17 |
| Author(s) : Giovannini MG , Scali C , Bartolini L , Schmidt B , Pepeu G |
| Ref : European Journal of Pharmacology , 354 :17 , 1998 |
| PubMedID: 9726626 |
| Title : Invited review: Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications - Giacobini_1998_Neurochem.Int_32_413 |
| Author(s) : Giacobini E |
| Ref : Neurochem Int , 32 :413 , 1998 |
| PubMedID: 9676739 |
| Title : Synthesis and evaluation of tacrine-huperzine A hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of Alzheimer's disease - Badia_1998_Bioorg.Med.Chem_6_427 |
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| Ref : Bioorganic & Medicinal Chemistry , 6 :427 , 1998 |
| PubMedID: 9597187 |
| Title : Comparative studies of huperzine A, E2020, and tacrine on behavior and cholinesterase activities - Cheng_1998_Pharmacol.Biochem.Behav_60_377 |
| Author(s) : Cheng DH , Tang XC |
| Ref : Pharmacol Biochem Behav , 60 :377 , 1998 |
| PubMedID: 9632220 |
| Title : Tacrine and donepezil attenuate the neurotoxic effect of A beta(25-35) in rat PC12 cells - Svensson_1998_Neuroreport_9_1519 |
| Author(s) : Svensson AL , Nordberg A |
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| PubMedID: 9631459 |
| Title : Inhibition of cholinesterase-associated aryl acylamidase activity by anticholinesterase agents: focus on drugs potentially effective in Alzheimer's disease - Costagli_1998_Biochem.Pharmacol_55_1733 |
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| Ref : Biochemical Pharmacology , 55 :1733 , 1998 |
| PubMedID: 9634011 |
| Title : Reversal of scopolamine-induced deficits in radial maze performance by (-)-huperzine A: comparison with E2020 and tacrine - Wang_1998_Eur.J.Pharmacol_349_137 |
| Author(s) : Wang T , Tang XC |
| Ref : European Journal of Pharmacology , 349 :137 , 1998 |
| PubMedID: 9671090 |
| Title : Capillary zone electrophoretic determination of some drugs against Alzheimer's disease - Vargas_1998_J.Chromatogr.A_802_121 |
| Author(s) : Vargas MG , Havel J , Patocka J |
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| PubMedID: 9588015 |
| Title : Safety of tacrine: clinical trials, treatment IND, and postmarketing experience - Gracon_1998_Alzheimer.Dis.Assoc.Disord_12_93 |
| Author(s) : Gracon SI , Knapp MJ , Berghoff WG , Pierce M , DeJong R , Lobbestael SJ , Symons J , Dombey SL , Luscombe FA , Kraemer D |
| Ref : Alzheimer Disease & Associated Disorders , 12 :93 , 1998 |
| PubMedID: 9651138 |
| Title : Frontal dysfunction blocks the therapeutic effect of THA on attention in Alzheimer's disease - Riekkinen_1997_Neuroreport_8_1845 |
| Author(s) : Riekkinen P, Jr. , Riekkinen M , Soininen H , Kuikka J , Laakso M , Riekkinen P, Sr. |
| Ref : Neuroreport , 8 :1845 , 1997 |
| PubMedID: 9223063 |
| Title : The effects of chronic tacrine therapy on d-tubocurarine blockade in the soleus and tibialis muscles of the rat - Ibebunjo_1997_Anesth.Analg_85_431 |
| Author(s) : Ibebunjo C , Donati F , Fox GS , Eshelby D , Tchervenkov JI |
| Ref : Anesthesia & Analgesia , 85 :431 , 1997 |
| PubMedID: 9249126 |
| Title : Tremulous jaw movements induced by the acetylcholinesterase inhibitor tacrine: effects of antiparkinsonian drugs - Cousins_1997_Eur.J.Pharmacol_322_137 |
| Author(s) : Cousins MS , Carriero DL , Salamone JD |
| Ref : European Journal of Pharmacology , 322 :137 , 1997 |
| PubMedID: 9098680 |
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| PubMedID: 9130291 |
| Title : Metabolic disposition of the cognition activator tacrine in rats, dogs, and humans. Species comparisons - Pool_1997_Drug.Metab.Dispos_25_590 |
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| PubMedID: 9152598 |
| Title : Effects of 9-amino-1,2,3,4-tetrahydroacridine (THA) on ATP diphosphohydrolase (EC 3.6.1.5) and 5'-nucleotidase (EC 3.1.3.5) from rat brain synaptosomes - Bonan_1997_Gen.Pharmacol_28_761 |
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| PubMedID: 9184816 |
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| PubMedID: 9202137 |
| Title : Prevention of amitriptyline-induced avoidance impairment by tacrine in mice - Pavone_1997_Behav.Brain.Res_89_229 |
| Author(s) : Pavone F , Battaglia M , Sansone M |
| Ref : Behavioural Brain Research , 89 :229 , 1997 |
| PubMedID: 9475630 |
| Title : Alzheimer's disease: an overview for the pharmacist - McGuffey_1997_J.Am.Pharm.Assoc_3_347 |
| Author(s) : McGuffey EC |
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| PubMedID: 9170813 |
| Title : Enhanced performance of spatial and visual recognition memory tasks by the selective acetylcholinesterase inhibitor E2020 in rhesus monkeys - Rupniak_1997_Psychopharmacology_131_406 |
| Author(s) : Rupniak NM , Tye SJ , Field MJ |
| Ref : Psychopharmacology , 131 :406 , 1997 |
| PubMedID: 9226744 |
| Title : Effects of NIK-247 on cholinesterase and scopolamine-induced amnesia [published erratum appears in Methods Find Exp Clin Pharmacol 1997 Jun\;19(5):364] - Kojima_1997_Methods.Find.Exp.Clin.Pharmacol_19_245 |
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| PubMedID: 9228650 |
| Title : Functional activation of cerebral blood flow abolished by scopolamine is reversed by cognitive enhancers associated with cholinesterase inhibition: a positron emission tomography study in unanesthetized monkeys - Tsukada_1997_J.Pharmacol.Exp.Ther_281_1408 |
| Author(s) : Tsukada H , Kakiuchi T , Ando I , Ouchi Y |
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| PubMedID: 9190877 |
| Title : Combined cholinergic and 5-HT2 receptor activation suppresses thalamocortical oscillations in aged rats - Jakala_1997_Pharmacol.Biochem.Behav_56_713 |
| Author(s) : Jakala P , Riekkinen P, Jr. |
| Ref : Pharmacol Biochem Behav , 56 :713 , 1997 |
| PubMedID: 9130298 |
| Title : Pharmacological basis of drug therapy of Alzheimer's disease - Sharma_1997_Indian.J.Exp.Biol_35_1146 |
| Author(s) : Sharma A , Parikh V , Singh M |
| Ref : Indian J Exp Biol , 35 :1146 , 1997 |
| PubMedID: 9567741 |
| Title : Effects of cholinesterase inhibitors on the secretion of beta-amyloid precursor protein in cell cultures - Lahiri_1997_Ann.N.Y.Acad.Sci_826_416 |
| Author(s) : Lahiri DK , Farlow MR , Nurnberger JI, Jr. , Greig NH |
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| PubMedID: 9329715 |
| Title : Motor dysfunction produced by tacrine administration in rats - Carriero_1997_Pharmacol.Biochem.Behav_58_851 |
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| Ref : Pharmacol Biochem Behav , 58 :851 , 1997 |
| PubMedID: 9408186 |
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| PubMedID: 9381027 |
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| Author(s) : Jackson JJ , Soliman MR |
| Ref : Life Sciences , 58 :47 , 1996 |
| PubMedID: 8628110 |
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| Author(s) : Foster NL , Petersen RC , Gracon SI , Lewis K |
| Ref : Dementia , 7 :260 , 1996 |
| PubMedID: 8872417 |
| Title : Overlapping drug interaction sites of human butyrylcholinesterase dissected by site-directed mutagenesis - Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423 |
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| Ref : Molecular Pharmacology , 50 :1423 , 1996 |
| PubMedID: 8967962 |
| Gene_locus related to this paper: human-BCHE |
| Title : Huperzine A, a novel promising acetylcholinesterase inhibitor - Cheng_1996_Neuroreport_8_97 |
| Author(s) : Cheng DH , Ren H , Tang XC |
| Ref : Neuroreport , 8 :97 , 1996 |
| PubMedID: 9051760 |
| Title : Allosteric regulation of the binding of [3H]acetylcholine to m2 muscarinic receptors - Gnagey_1996_Biochem.Pharmacol_52_1767 |
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| Ref : Biochemical Pharmacology , 52 :1767 , 1996 |
| PubMedID: 8986140 |
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| PubMedID: 8667714 |
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| Ref : Chemistry & Biology , 2 :621 , 1995 |
| PubMedID: 9383467 |
| Title : Cholinesterase inhibitors proposed for treating dementia in Alzheimer's disease: selectivity toward human brain acetylcholinesterase compared with butyrylcholinesterase - Pacheco_1995_J.Pharmacol.Exp.Ther_274_767 |
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| PubMedID: 7636741 |
| Title : [New therapeutic prospects in Alzheimer disease] - Rouhart_1995_Rev.Med.Interne_16_860 |
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| PubMedID: 8570945 |
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| PubMedID: 7710736 |
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| PubMedID: 8415649 |
| Gene_locus related to this paper: torca-ACHE |
| Title : The next generation of cholinesterase inhibitors - Adem_1993_Acta.Neurol.Scand.Suppl_149_10 |
| Author(s) : Adem A |
| Ref : Acta Neurologica Scandinavica Supplementum , 149 :10 , 1993 |
| PubMedID: 8128831 |
| Title : Three distinct domains in the cholinesterase molecule confer selectivity for acetyl- and butyrylcholinesterase inhibitors - Radic_1993_Biochemistry_32_12074 |
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| Ref : Biochemistry , 32 :12074 , 1993 |
| PubMedID: 8218285 |
| Title : Cholinesterase inhibitor effects on extracellular acetylcholine in rat cortex - Messamore_1993_Neuropharmacol_32_745 |
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| Ref : Neuropharmacology , 32 :745 , 1993 |
| PubMedID: 8413838 |
| Title : Changes of rat blood and tissue cholinesterases following administration of tacrine derivatives in vivo - Bajgar_1993_Sb.Ved.Pr.Lek.Fak.Karlovy.Univerzity.Hradci.Kralove_36_73 |
| Author(s) : Bajgar J , Skopec F |
| Ref : Sbornik Vedeckych Praci Lekarske Fakulty Karlovy Univerzity , 36 :73 , 1993 |
| PubMedID: 8165433 |
| Title : Preferential inhibition of acetylcholinesterase molecular forms in rat brain - Ogane_1992_Neurochem.Res_17_489 |
| Author(s) : Ogane N , Giacobini E , Messamore E |
| Ref : Neurochemical Research , 17 :489 , 1992 |
| PubMedID: 1528356 |
| Title : In vitro protection of acetylcholinesterase and butyrylcholinesterase by tetrahydroaminoacridine. Comparison with physostigmine - Galli_1992_Biochem.Pharmacol_43_2427 |
| Author(s) : Galli A , Mori F , Gori I , Lucherini M |
| Ref : Biochemical Pharmacology , 43 :2427 , 1992 |
| PubMedID: 1610407 |
| Title : Effects of tacrine, velnacrine (HP029), suronacrine (HP128), and 3,4-diaminopyridine on skeletal neuromuscular transmission in vitro - Braga_1991_Br.J.Pharmacol_102_909 |
| Author(s) : Braga MF , Harvey AL , Rowan EG |
| Ref : British Journal of Pharmacology , 102 :909 , 1991 |
| PubMedID: 1649660 |
| Title : Reversibility of the inhibition of acetylcholinesterase by tacrine - Dawson_1990_Neurosci.Lett_118_85 |
| Author(s) : Dawson RM |
| Ref : Neuroscience Letters , 118 :85 , 1990 |
| PubMedID: 2259472 |
| Title : The mechanism of tetrahydroaminoacridine-evoked release of endogenous 5-hydroxytryptamine and dopamine from rat brain tissue prisms - Robinson_1989_Br.J.Pharmacol_98_1127 |
| Author(s) : Robinson TN , De Souza RJ , Cross AJ , Green AR |
| Ref : British Journal of Pharmacology , 98 :1127 , 1989 |
| PubMedID: 2611486 |
| Title : Inhibitory effect of 1,2,3,4-tetrahydro-9-aminoacridine on the depolarization-induced release of GABA from cerebral cortex - de Belleroche_1988_Br.J.Pharmacol_94_1017 |
| Author(s) : de Belleroche J , Gardiner IM |
| Ref : British Journal of Pharmacology , 94 :1017 , 1988 |
| PubMedID: 3207970 |