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Details

Stereochemistry ACHIRAL
Molecular Formula C9H15N5.C4H4O4
Molecular Weight 309.3211
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ALVAMELINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CCN1N=NC(=N1)C2=CCCN(C)C2

InChI

InChIKey=YKFYFAAWVQGVTP-BTJKTKAUSA-N
InChI=1S/C9H15N5.C4H4O4/c1-3-14-11-9(10-12-14)8-5-4-6-13(2)7-8;5-3(6)1-2-4(7)8/h5H,3-4,6-7H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C9H15N5
Molecular Weight 193.2489
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Alvameline is a partial agonist of the M1 mAChR that also displays M2/M3 antagonist effects. It readily crosses the blood-brain barrier. It has an effect profile that makes it of interest to test its ability to counteract bladder overactivity in humans. Behaviorally, alvameline has been shown to significantly improve Morris water maze (MWM) performance in both young and ageimpaired rats. It failed to improve cognition in patients with mild to moderate Alzheimer's disease.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Lu 25-109, a combined m1 agonist and m2 antagonist, modulates regulated processing of the amyloid precursor protein of Alzheimer's disease.
1998
A bridging study of LU 25-109 in patients with probable Alzheimer's disease.
1998
In vivo muscarinic cholinergic mediated effects of Lu 25-109, a M1 agonist and M2/M3 antagonist in vitro.
1998 Jun
Lu 25-109, a muscarinic agonist, fails to improve cognition in Alzheimer's disease. Lu25-109 Study Group.
2000 Jan 25
Actions of the new antimuscarinic compound Lu 25-109 on isolated human and pig detrusor.
2002
Patents

Sample Use Guides

In Vivo Use Guide
25, 50, or 100 mg three times a day
Route of Administration: Oral
In Vitro Use Guide
Radioligand binding experiments demonstrated a small difference in affinity for Alvameline in the parotid gland compared with the bladder, the pKi values being 6.2 versus 6.5 (n=4).
Substance Class Chemical
Created
by admin
on Tue Oct 22 01:24:37 UTC 2019
Edited
by admin
on Tue Oct 22 01:24:37 UTC 2019
Record UNII
76732QSQ30
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALVAMELINE MALEATE
USAN  
USAN  
Official Name English
PYRIDINE, 3-(2-ETHYL-2H-TETRAZOL-5-YL)-1,2,5,6-TETRAHYDRO-1-METHYL-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
LU 25-109-M
Code English
ALVAMELINE MALEATE [USAN]
Common Name English
LU-25-109-M
Code English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Tue Oct 22 01:24:37 UTC 2019 , Edited by admin on Tue Oct 22 01:24:37 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL131428
Created by admin on Tue Oct 22 01:24:37 UTC 2019 , Edited by admin on Tue Oct 22 01:24:37 UTC 2019
PRIMARY
PUBCHEM
6450824
Created by admin on Tue Oct 22 01:24:37 UTC 2019 , Edited by admin on Tue Oct 22 01:24:37 UTC 2019
PRIMARY
CAS
219581-36-9
Created by admin on Tue Oct 22 01:24:37 UTC 2019 , Edited by admin on Tue Oct 22 01:24:37 UTC 2019
PRIMARY
NCI_THESAURUS
C76609
Created by admin on Tue Oct 22 01:24:37 UTC 2019 , Edited by admin on Tue Oct 22 01:24:37 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY