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Inhibitor Report for: 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



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
IUPHAR: 6687
Wikipedia:

Target families
Tacrine ligand of proteins in family: ACHE

Stucture of targets
5 structures (e.g. : 1ACJ, 7XN1, 7E3I... more)

Protein target

References
Search PubMed for references concerning: Tacrine

62 more
    Title: Crystal structure of human acetylcholinesterase in complex with tacrine: Implications for drug discovery
    Dileep KV, Ihara K, Mishima-Tsumagari C, Kukimoto-Niino M, Yonemochi M, Hanada K, Shirouzu M, Zhang KYJ
    Ref: Int J Biol Macromol, :, 2022 : PubMed

            

    Title: Kinetic analysis of the toxicological effect of tacrine (Cognex) on human retinal acetylcholinesterase activity
    Alhomida AS, Al-Rajhi AA, Kamal MA, Al-Jafari AA
    Ref: Toxicology, 147:33, 2000 : PubMed

            

    Title: The effect of cytochromes P4501A induction and inhibition on the disposition of the cognition activator tacrine in rat hepatic preparations
    Bezek S, Kukan M, Pool WF, Woolf TF
    Ref: Xenobiotica, 26:935, 1996 : PubMed

            


human-ACHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for human-ACHE (22)

human-BCHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for human-BCHE (24)

mouse-ACHE
MutationKiKsiIc50SubstrateConditionPaper
WT 40 & 10 nM 130 & 50 nM - Acetylthiocholine 100mM NaP pH7.0 T22C Radic_1993_Biochemistry_32_12074
Y337A 1.5 & 0.5 nM 5 & 1 nM - Acetylthiocholine 100mM NaP pH7.0 T22C Radic_1993_Biochemistry_32_12074
Y337F 150 & 30 nM 680 & 180 nM - Acetylthiocholine 100mM NaP pH7.0 T22C Radic_1993_Biochemistry_32_12074

mouse-BCHE
MutationKiKsiIc50SubstrateConditionPaper
WT 17 & 4 nM 47 & 22 nM - Acetylthiocholine 100mM NaP pH7.0 T22C Radic_1993_Biochemistry_32_12074

WT Kinetics
Kinetic parametersKiKsiIc50SubstrateConditionsPapers
human-ACHE0.21 uM-- Acetylthiocholine 50mM NaPhosphate pH7.4 Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423
human-ACHE12 nM-- Acetylthiocholine T25C IS 50 mM phosphate Kaplan_2001_Biochemistry_40_7433
human-ACHE85 & 12 nM 90 & 20 nM - Acetylthiocholine 50mM Na phosphate pH8 T22C Ariel_1998_Biochem.J_335_95
human-BCHE12 nM-- Acetylthiocholine T25C IS 50 mM phosphate Kaplan_2001_Biochemistry_40_7433
human-BCHE0.06 & 0.03 uM-- Butyrylthiocholine 50mM NaPhosphate pH7.4 Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423
mouse-ACHE40 & 10 nM130 & 50 nM- Acetylthiocholine 100mM NaP pH7.0 T22C Radic_1993_Biochemistry_32_12074
mouse-BCHE17 & 4 nM47 & 22 nM- Acetylthiocholine 100mM NaP pH7.0 T22C Radic_1993_Biochemistry_32_12074