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+

HIDE SMILES / InChI

Molecular Formula	C25H32N2O
Molecular Weight	376.5344
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8667190 \| https://www.ncbi.nlm.nih.gov/pubmed/11763163	Inhibitor 8504		51.2 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14535624	Primary		Phase III 665	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:40:08 GMT 2025` Edited by `admin` on `Mon Mar 31 21:40:08 GMT 2025`
Record UNII	7Y1T8FKO1V
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TAK-147

Preferred Name

English

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

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