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Details

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

SHOW SMILES / InChI
Structure of ALVAMELINE

SMILES

CCN1N=NC(=N1)C2=CCCN(C)C2

InChI

InChIKey=RNMOMKCRCIRYCZ-UHFFFAOYSA-N
InChI=1S/C9H15N5/c1-3-14-11-9(10-12-14)8-5-4-6-13(2)7-8/h5H,3-4,6-7H2,1-2H3

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

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
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 Sat Dec 16 16:21:33 GMT 2023
Edited
by admin
on Sat Dec 16 16:21:33 GMT 2023
Record UNII
4XFD7B36M6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALVAMELINE
INN   WHO-DD  
INN  
Official Name English
Alvameline [WHO-DD]
Common Name English
alvameline [INN]
Common Name English
LU 25-109
Code English
5-(2-ETHYL-2H-TETRAZOL-5-YL)-1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE
Systematic Name English
PYRIDINE, 3-(2-ETHYL-2H-TETRAZOL-5-YL)-1,2,5,6-TETRAHYDRO-1-METHYL-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
Code System Code Type Description
INN
7742
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL131428
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
SMS_ID
100000085127
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
PUBCHEM
178030
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
NCI_THESAURUS
C77842
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
EVMPD
SUB00420MIG
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
WIKIPEDIA
ALVAMELINE
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
CAS
120241-31-8
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
FDA UNII
4XFD7B36M6
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID30152748
Created by admin on Sat Dec 16 16:21:35 GMT 2023 , Edited by admin on Sat Dec 16 16:21:35 GMT 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MUSCARINIC ACETYLCHOLINE RECEPTOR M2
TARGET -> INHIBITOR
Structure of ALVAMELINE
EXCRETED UNCHANGED
AMOUNT EXCRETED
USP
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
MUSCARINIC ACETYLCHOLINE RECEPTOR M3
TARGET -> INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of ALVAMELINE MALEATE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2A6
METABOLIC ENZYME -> SUBSTRATE
MUSCARINIC ACETYLCHOLINE RECEPTOR M1
TARGET->PARTIAL AGONIST
Related Record Type Details
Structure of LU-35-038
METABOLITE -> PARENT
Structure of LU-25-077
METABOLITE ACTIVE -> PARENT
PLASMA
Structure of LU-31-190
METABOLITE -> PARENT
Structure of LU-32-181
METABOLITE -> PARENT
PLASMA
Structure of LU-31-126
METABOLITE -> PARENT
MAJOR
URINE
Structure of LU-35-026
METABOLITE -> PARENT
MAJOR
FECAL; PLASMA
Structure of LU-29-297
METABOLITE -> PARENT
Related Record Type Details
Structure of ALVAMELINE
ACTIVE MOIETY
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