VELNACRINE FUMARATE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H14N2O.C4H4O4
Molecular Weight	330.3352
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.NC1=C2C(O)CCCC2=NC3=C1C=CC=C3

InChI

InChIKey=NEEKVKZFYBQFGT-WLHGVMLRSA-N

InChI=1S/C13H14N2O.C4H4O4/c14-13-8-4-1-2-5-9(8)15-10-6-3-7-11(16)12(10)13;5-3(6)1-2-4(7)8/h1-2,4-5,11,16H,3,6-7H2,(H2,14,15);1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula	C13H14N2O
Molecular Weight	214.2631
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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.google.com/patents/US4631286 | http://adisinsight.springer.com/drugs/800000572 | https://www.ncbi.nlm.nih.gov/pubmed/15106259

Velnacrine (9-amino-1,2,3,4-tetrahydroacridin-1-ol) is an inhibitor of acetylcholinesterase. It was studied for the treatment of Alzheimer's disease however development was discontinued. There has been no research into the use of velnacrine as a cognitive enhancer in the treatment of Alzheimer's disease since 1994. The FDA peripheral and CNS drug advisory board voted unanimously against recommending approval. This review shows the toxic nature of velnacrine, and provides no evidence of efficacy.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: http://adisinsight.springer.com/drugs/800000572 \| https://www.google.com/patents/US4631286	Inhibitor 8504		0.79 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15106259	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
213 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2592587/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
175 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2592587/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
49.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
91.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
226.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
284 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
886 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2592587/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
946 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2592587/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
163.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
294 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
809.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1110.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2592587/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2592587/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2229455/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Analyte	Population
45.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739821/	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
48.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739821/	VELNACRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
47% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739821/	VELNACRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
150 mg 3 times / day multiple, oral Highest recorded dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	Disc. AE: Hyperventilation, Syncope... Other AEs: Vomiting... AEs leading to discontinuation/dose reduction: Hyperventilation (16.7%) Syncope (16.7%) Dizziness (16.7%) Fainting Headache Other AEs: Vomiting Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/
100 mg 3 times / day multiple, oral Highest studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2229455/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/2229455/	Sources: https://pubmed.ncbi.nlm.nih.gov/2229455/

AEs

AE	Significance	Dose	Population
Vomiting		150 mg 3 times / day multiple, oral Highest recorded dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/
Dizziness	16.7% Disc. AE	150 mg 3 times / day multiple, oral Highest recorded dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/
Hyperventilation	16.7% Disc. AE	150 mg 3 times / day multiple, oral Highest recorded dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/
Syncope	16.7% Disc. AE	150 mg 3 times / day multiple, oral Highest recorded dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/
Fainting	Disc. AE	150 mg 3 times / day multiple, oral Highest recorded dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/
Headache	Disc. AE	150 mg 3 times / day multiple, oral Highest recorded dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1421679/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 OATP1B1 1079

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIzNDU1In19	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIzNDU1In19	yes [Inhibition 10 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjM0NTUifX0=

PubMed

Title	Date	PubMed
Velnacrine for Alzheimer's disease.	2004	15106259

Patents

Sample Use Guides

In Vivo Use Guide

Velnacrine for the treatment of Alzheimer's disease (a double-blind, placebo-controlled trials): 10, 25, 50 and 75 mg t.i.d. The 225 mg/day dose appears to be safe for use in multicenter outpatient trials of velnacrine efficacy in Alzheimer's disease.

Route of Administration: Oral

In Vitro Use Guide

Human erythrocyte suspensions were incubated with acetylcholine and choline in the absence or presence of 10 microM atropine or 10 microM velnacrine maleate.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:10:42 GMT 2025` Edited by `admin` on `Mon Mar 31 23:10:42 GMT 2025`
Record UNII	Z2589Z87DE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VELNACRINE FUMARATE

Common Name

English

1-ACRIDINOL, 9-AMINO-1,2,3,4-TETRAHYDRO-, (2E)-2-BUTENEDIOATE (1:1) (SALT)

Preferred Name

English

Code System Code Type Description

CAS

333408-28-9

Created by admin on Mon Mar 31 23:10:42 GMT 2025 , Edited by admin on Mon Mar 31 23:10:42 GMT 2025

PRIMARY

PUBCHEM

6364836

Created by admin on Mon Mar 31 23:10:42 GMT 2025 , Edited by admin on Mon Mar 31 23:10:42 GMT 2025

PRIMARY

FDA UNII

Z2589Z87DE

Created by admin on Mon Mar 31 23:10:42 GMT 2025 , Edited by admin on Mon Mar 31 23:10:42 GMT 2025

PRIMARY

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VELNACRINE

PARENT -> SALT/SOLVATE

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					Y2P6NV151K

VELNACRINE

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.google.com/patents/US4631286 | http://adisinsight.springer.com/drugs/800000572 | https://www.ncbi.nlm.nih.gov/pubmed/15106259

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Tox targets

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.google.com/patents/US4631286 | http://adisinsight.springer.com/drugs/800000572 | https://www.ncbi.nlm.nih.gov/pubmed/15106259

C_max

T_1/2

F_unbound

Drug as perpetrator