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Details

Stereochemistry ACHIRAL
Molecular Formula C9H15N5.C4H4O4
Molecular Weight 309.3211
Optical Activity NONE
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 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: DOI: 10.1016/0024-3205(95)93724-S
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800001965 | https://www.ncbi.nlm.nih.gov/pubmed/10668706

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

Lundbeck
43
Sources: DOI: 10.1016/0024-3205(95)93724-S

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Muscarinic acetylcholine receptor M1
169
Target ID: CHEMBL276
Sources: doi: 10.1016/0024-3205(95)93724-S
Partial Agonist
290
cholinergic receptor, muscarinic 2
7
Target ID: 1.00715344E8
Gene Symbol: Chrm2
Sources: DOI: 10.1016/0024-3205(95)93724-S
Antagonist
2778
Muscarinic acetylcholine receptor M3
159
Target ID: CHEMBL245
Sources: DOI: 10.1016/0024-3205(95)93724-S
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9488097/
125 mg 3 times / day multiple, oral
dose: 125 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALVAMELINE serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9488097/
150 mg 3 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALVAMELINE serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
150 mg 3 times / day multiple, oral (unknown)
MTD
Dose: 150 mg, 3 times / day
Route: oral
Route: multiple
Dose: 150 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
200 mg 3 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
Disc. AE: Epigastric pain...
Other AEs: vomiting, Dizziness...
AEs leading to
discontinuation/dose reduction:
Epigastric pain (severe, 1 pt)
Other AEs:
vomiting (severe, 1 pt)
Dizziness (severe, 1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
AEs

AEs

AESignificanceDosePopulation
Dizziness severe, 1 pt
200 mg 3 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
vomiting severe, 1 pt
200 mg 3 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
Epigastric pain severe, 1 pt
Disc. AE
200 mg 3 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/9488097
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
FMO3
67

MAO
2

CYP1A2
1054

CYP4A9/11
5

CYP2E1
667

CYP2A6
543

CYP2C19
991
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2E1
667
 likely
CYP2C9
1037
 no
CYP4A9/11
5
 no
FMO3
67
 no
MAO
2
 no
CYP1A2
1054
 yes
CYP2A6
543
 yes
CYP2C19
991
 yes
CYP2D6
1217
 yes
CYP3A4
1737
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
BOC Sciences
120241-31-8
http://www.bocsci.com/description.asp?cas=120241-31-8
Chemspace
CSC000094528
https://chem-space.com/CSC000094528
Compound Cloud
178030
Compound Cloud
6450824
Enamine
BBV-38311169
http://www.enaminestore.com/catalog/BBV-38311169
Hangzhou Yuhao Chemical Technology
YH65699
MuseChem
I000458
https://www.musechem.com/product/I000458.html
eMolecules
110045729
https://orderbb.emolecules.com/search/#?query=110045729
eMolecules
300769792
https://orderbb.emolecules.com/search/#?query=300769792
mcule
MCULE-1835335922
https://mcule.com/MCULE-1835335922/
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
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

Patents

EP1017386A1
2
EP1336602A1
4
US20030092737
2
US6936621
2

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 Fri Dec 15 15:42:43 UTC 2023
Edited
by admin
on Fri Dec 15 15:42:43 UTC 2023
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 Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL131428
Created by admin on Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
PRIMARY
PUBCHEM
6450824
Created by admin on Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
PRIMARY
CAS
219581-36-9
Created by admin on Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
PRIMARY
FDA UNII
76732QSQ30
Created by admin on Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
PRIMARY
USAN
NN-35
Created by admin on Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
PRIMARY
NCI_THESAURUS
C76609
Created by admin on Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
PRIMARY
SMS_ID
300000044455
Created by admin on Fri Dec 15 15:42:43 UTC 2023 , Edited by admin on Fri Dec 15 15:42:43 UTC 2023
PRIMARY
Related Record Type Details
Structure of ALVAMELINE
PARENT -> SALT/SOLVATE
Structure of MALEIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ALVAMELINE
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