ZANAPEZIL FUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H32N2O.C4H4O4
Molecular Weight	492.6065
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.O=C(CCC1CCN(CC2=CC=CC=C2)CC1)C3=CC4=C(CCCCN4)C=C3

InChI

InChIKey=CWEHWZPCDBRUNO-WLHGVMLRSA-N

InChI=1S/C25H32N2O.C4H4O4/c28-25(23-11-10-22-8-4-5-15-26-24(22)18-23)12-9-20-13-16-27(17-14-20)19-21-6-2-1-3-7-21;5-3(6)1-2-4(7)8/h1-3,6-7,10-11,18,20,26H,4-5,8-9,12-17,19H2;1-2H,(H,5,6)(H,7,8)/b;2-1+

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8057278 | https://www.ncbi.nlm.nih.gov/pubmed/8667190

Zanapezil (TAK-147) is a selective reversible acetylcholine (ACh) esterase inhibitor that was designed as a drug for Alzheimer's disease (AD) treatment. The development of the drug was discontinued due to a lack of a dose-dependent effect in the trials.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8667190 \| https://www.ncbi.nlm.nih.gov/pubmed/11763163	Inhibitor 8297		51.2 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14535624	Primary		Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of 3-[1-(phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone fumarate, a novel acetylcholinesterase inhibitor, on spatial cognitive impairment induced by chronic cerebral hypoperfusion in rats.	2002 Oct 4	12359317
Comparison of the effect of TAK-147 (zanapezil) and E-2020 (donepezil) on extracellular acetylcholine level and blood flow in the ventral hippocampus of freely moving rats.	2004 Jun 25	15158174
Effect of oral administration of zanapezil (TAK-147) for 21 days on acetylcholine and monoamines levels in the ventral hippocampus of freely moving rats.	2005 Aug	15951830

Patents

Sample Use Guides

In Vivo Use Guide

Daily oral administration of TAK-147 (1 mg/kg) for 40 days increased phosphocreatine and ATP levels in brains of aged Fischer rats.

Route of Administration: Oral

In Vitro Use Guide

The inhibitory potency of TAK-147 towards AChE activity (IC50) was found to be 51.2 nM in vitro. AChE activities were measured using the radioisotopic method on male Wistar rats' cerebral cortices.

Name

Type

Language

ZANAPEZIL FUMARATE

Common Name

English

ZANAPEZIL FUMARATE [JAN]

Common Name

English

1-PROPANONE, 3-(1-(PHENYLMETHYL)-4-PIPERIDINYL)-1-(2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPIN-8-YL)-, (2E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

TAK-147

Common Name

English

1-PROPANONE, 3-(1-(PHENYLMETHYL)-4-PIPERIDINYL)-1-(2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPIN-8-YL)-, (E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

263248-42-6