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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H25NO4.C6H12O7
Molecular Weight 587.6149
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Benzgalantamine Gluconate

SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.COC1=CC=C2CN(C)CC[C@@]34C=C[C@@H](C[C@@H]3OC1=C24)OC(=O)C5=CC=CC=C5

InChI

InChIKey=YOMFDYFCNHSIAU-MXJKWOHVSA-N
InChI=1S/C24H25NO4.C6H12O7/c1-25-13-12-24-11-10-18(28-23(26)16-6-4-3-5-7-16)14-20(24)29-22-19(27-2)9-8-17(15-25)21(22)24;7-1-2(8)3(9)4(10)5(11)6(12)13/h3-11,18,20H,12-15H2,1-2H3;2-5,7-11H,1H2,(H,12,13)/t18-,20-,24-;2-,3-,4+,5-/m01/s1

HIDE SMILES / InChI

Molecular Formula C6H12O7
Molecular Weight 196.1553
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C24H25NO4
Molecular Weight 391.4596
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68005702 | https://www.ncbi.nlm.nih.gov/pubmed/12177686

Galantamine (RAZADYNE®, galantamine hydrobromide) is a benzazepine derived from norbelladine. It is found in Galanthus and other Amaryllidaceae. It is a reversible, competitive acetylcholinesterase inhibitor that is used for the treatment of mild to moderate dementia of the Alzheimer’s type. Although the etiology of cognitive impairment in Alzheimer’s disease is not fully understood, it has been reported that acetylcholine-producing neurons degenerate in the brains of patients with Alzheimer’s disease. The degree of this cholinergic loss has been correlated with degree of cognitive impairment and density of amyloid plaques (a neuropathological hallmark of Alzheimer’s disease). While the precise mechanism of galantamine’s (RAZADYNE®, galantamine hydrobromide) action is unknown, it is postulated to exert its therapeutic effect by enhancing cholinergic function. This is accomplished by increasing the concentration of acetylcholine through reversible inhibition of its hydrolysis by acetylcholinesterase. If this mechanism is correct, galantamine’s (RAZADYNE®, galantamine hydrobromide) effect may lessen as the disease process advances and fewer cholinergic neurons remain functionally intact. There is no evidence that galantamine (RAZADYNE®, galantamine hydrobromide) alters the course of the underlying dementing process.

Originator

Curator's Comment: # Janssen Pharmaceuticals, a division of Ortho-McNeil-Jannsen Pharmaceuticals

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.35 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
RAZADYNE

Approved Use

Galantamine hydrobromide is a cholinesterase inhibitor indicated for the treatment of mild to moderate dementia of the Alzheimer’s type.

Launch Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
84.3 ng/mL
24 mg single, oral
dose: 24 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GALANTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1050 ng × h/mL
24 mg single, oral
dose: 24 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GALANTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.53 h
24 mg single, oral
dose: 24 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GALANTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
82%
GALANTAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
8 mg 2 times / day steady, oral
Dose: 8 mg, 2 times / day
Route: oral
Route: steady
Dose: 8 mg, 2 times / day
Sources:
unhealthy, 90 years
Health Status: unhealthy
Age Group: 90 years
Sex: M
Sources:
Disc. AE: Nightmares...
AEs leading to
discontinuation/dose reduction:
Nightmares (1 patient)
Sources:
32 mg 1 times / day steady, oral
Highest studied dose
Dose: 32 mg, 1 times / day
Route: oral
Route: steady
Dose: 32 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (42%)
Vomiting (21%)
Diarrhea (16%)
Anorexia (15%)
Weight loss (8%)
Dizziness (15%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nightmares 1 patient
Disc. AE
8 mg 2 times / day steady, oral
Dose: 8 mg, 2 times / day
Route: oral
Route: steady
Dose: 8 mg, 2 times / day
Sources:
unhealthy, 90 years
Health Status: unhealthy
Age Group: 90 years
Sex: M
Sources:
Anorexia 15%
32 mg 1 times / day steady, oral
Highest studied dose
Dose: 32 mg, 1 times / day
Route: oral
Route: steady
Dose: 32 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Dizziness 15%
32 mg 1 times / day steady, oral
Highest studied dose
Dose: 32 mg, 1 times / day
Route: oral
Route: steady
Dose: 32 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Diarrhea 16%
32 mg 1 times / day steady, oral
Highest studied dose
Dose: 32 mg, 1 times / day
Route: oral
Route: steady
Dose: 32 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Vomiting 21%
32 mg 1 times / day steady, oral
Highest studied dose
Dose: 32 mg, 1 times / day
Route: oral
Route: steady
Dose: 32 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea 42%
32 mg 1 times / day steady, oral
Highest studied dose
Dose: 32 mg, 1 times / day
Route: oral
Route: steady
Dose: 32 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Weight loss 8%
32 mg 1 times / day steady, oral
Highest studied dose
Dose: 32 mg, 1 times / day
Route: oral
Route: steady
Dose: 32 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [Activation 15.8489 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no
no
no
no
no (co-administration study)
Comment: Coadministration of Galantamine (multiple doses) had no effect on the pharmacokinetics of R-/S-Warfarin (CYP2C9 substrate)
Page: 4, 20, (ClinPharm) 34, 38-39
yes [IC50 0.6 uM]
no (co-administration study)
Comment: Coadministration of Galantamine (multiple doses) had no effect on the pharmacokinetics of Digoxin (P-gp substrate)
Page: 4, 20, (ClinPharm) 38, 40
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major [Km 187 uM]
yes (co-administration study)
Comment: Vmax = 5.2 nmol/mg protein/h (Pharmacogenetics, 9, 661 (1999)); Coadministration (multiple doses) of ketoconazole (strong CYP3A4 inhibitor, CYP2D6 inhibitor) and paroxetin (strong CYP2D6 inhibitor) increased Galantamine AUC by 30% and 40%.
Page: 2, 4, 19-20, (ClinPharm) 15, 38, 42-23, 45
major
yes (co-administration study)
Comment: Coadministration (multiple doses) of ketoconazole (strong CYP3A4 inhibitor, CYP2D6 inhibitor) increased Galantamine AUC by 30%. Coadministration of erythromycin (moderate CYP3A4 inhibitor) increased Galantamine AUC by only 10%.
Page: 2, 4, 19-20, (ClinPharm) 15, 38, 42-44
yes
Tox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Unconventional ligands and modulators of nicotinic receptors.
2002-12
The cholinergic approach for the treatment of vascular dementia: evidence from pre-clinical and clinical studies.
2002-11-27
[Rivastigmine: a review of its clinical effectiveness].
2002-11-19
[Treatment of Alzheimer's disease].
2002-11-19
The rationale behind cholinergic drug treatment for dementia related to cerebrovascular disease.
2002-11-15
Treatment options: the latest evidence with galantamine (Reminyl).
2002-11-15
Use of galantamine to treat vascular dementia.
2002-11-09
Use of galantamine to treat vascular dementia.
2002-11-09
Galantamine improved cognition and global functioning in vascular dementia or Alzheimer disease with cerebrovascular disease.
2002-11-07
Adjuvant galantamine administration improves negative symptoms in a patient with treatment-refractory schizophrenia.
2002-11-01
Efficacy of galantamine in probable vascular dementia and Alzheimer's disease combined with cerebrovascular disease: a randomized trial.
2002-11
A nitric oxide-donating flurbiprofen derivative reduces neuroinflammation without interacting with galantamine in the rat.
2002-10-25
Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts.
2002-10-11
Cognitive pharmacotherapy of Alzheimer's disease and other dementias.
2002-10
[Galantamine: a novel cholinergic agent for Alzheimer's disease].
2002-10
The impact of journal advertisements on prescribers of cholinesterase inhibitors.
2002-10
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
2002-09-16
Galantamine provides broad benefits in patients with 'advanced moderate' Alzheimer's disease (MMSE < or = 12) for up to six months.
2002-09
Broad therapeutic benefits in patients with probable vascular dementia or Alzheimer's disease with cerebrovascular disease after treatment with galantamine.
2002-09
Galantamine pharmacokinetics, safety, and tolerability profiles are similar in healthy Caucasian and Japanese subjects.
2002-09
Efficacy of galantamine in probable vascular dementia and Alzheimer's disease combined with cerebrovascular disease: a randomized trial.
2002-09
To what degree does cognitive impairment in Alzheimer's disease predict dependence of patients on caregivers?
2002-08-19
An efficient enantioselective synthesis of (-)-galanthamine.
2002-08-02
[Nicotinic Receptor, galantamine and Alzheimer disease].
2002-07-23
Medical treatment of Alzheimer's disease: past, present, and future.
2002-07
Galantamine for treatment-resistant schizophrenia.
2002-07
Galanthamine as bis-functional ligand for the acetylcholinesterase.
2002-06
Switching cholinesterase inhibitors in patients with Alzheimer's disease.
2002-06
Evidence that the clinical effects of cholinesterase inhibitors are related to potency and targeting of action.
2002-06
The tolerability and safety of cholinesterase inhibitors in the treatment of dementia.
2002-06
The efficacy of cholinesterase inhibitors in treating the behavioural symptoms of dementia.
2002-06
[Latest therapies for treating dementia].
2002-05-15
[Dementing disorders. What benefits do the new anti-dementia drugs have?].
2002-05-06
Pharmacologic treatments of dementia.
2002-05
The nicotinic allosteric potentiating ligand galantamine facilitates synaptic transmission in the mammalian central nervous system.
2002-05
Efficacy of galantamine in probable vascular dementia and Alzheimer's disease combined with cerebrovascular disease: a randomised trial.
2002-04-13
Galantamine for vascular dementia: some answers, some questions.
2002-04-13
New drugs 2002, part 1.
2002-01
Nicotinic receptor modulation: advantages for successful Alzheimer's disease therapy.
2002
Clinical and cost-effectiveness of donepezil, rivastigmine, and galantamine for Alzheimer's disease. A systematic review.
2002
Galantamine: a pharmacoeconomic review of its use in Alzheimer's disease.
2002
Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease.
2002
Clinical pharmacokinetics and pharmacodynamics of cholinesterase inhibitors.
2002
[New theory! Galantamine and nicotinic-cholinergic transmission].
2002
Economic analysis of galantamine, a cholinesterase inhibitor, in the treatment of patients with mild to moderate Alzheimer's disease in the Netherlands.
2002
Assessment of Health Economics in Alzheimer's Disease (AHEAD): treatment with galantamine in Sweden.
2002
Galantamine for Alzheimer's disease.
2002
Cholinergic medication for neuroleptic-induced tardive dyskinesia.
2002
Understanding and managing behavioural symptoms in Alzheimer's disease and related dementias: focus on rivastigmine.
2002
A non-cholinergic, trophic action of acetylcholinesterase on hippocampal neurones in vitro: molecular mechanisms.
2002
Patents

Sample Use Guides

The recommended starting dosage of RAZADYNE® tablets is 4 mg twice a day (8 mg/day). The dosage should be increased to the initial maintenance dosage of 8 mg twice a day (16 mg/day) after a minimum of 4 weeks. A further increase to 12 mg twice a day (24 mg/day) should be attempted after a minimum of 4 weeks at 8 mg twice a day (16 mg/day). Dosage increases should be based upon assessment of clinical benefit and tolerability of the previous dose.
Route of Administration: Oral
In Vitro Use Guide
Galanthamine was evaluated as inhibitor of human acetylcholinesterase activity from samples of postmortem human brain, fresh brain cortex biopsies and human erythrocytes. The respective galanthamine concentration exerting a half maximal effect (IC50) on acetylcholinesterase in postmortem human brain frontal cortex was 3.2 uM versus 2.8 uM in the hippocampus region. In addition, galanthamine was 10-fold less potent in inhibiting the enzyme activity from human brain that from human erythrocytes.
Substance Class Chemical
Created
by admin
on Wed Apr 02 03:26:29 GMT 2025
Edited
by admin
on Wed Apr 02 03:26:29 GMT 2025
Record UNII
LN7PMJ4P57
Record Status Validated (UNII)
Record Version
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Name Type Language
Benzgalantamine Gluconate
USAN  
Official Name English
ZUNVEYL
Preferred Name English
MEMOGAIN GLUCONATE
Common Name English
D-Gluconic acid, compd. with (4aS,6R,8aS)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-yl benzoate (1:1)
Systematic Name English
Galantamine benzoate gluconate
Common Name English
GLN-1062 GLUCONATE
Code English
ALPHA-1062 gluconate
Code English
GLUCONIC ACID SALT OF GALANTAMINE BENZOATE
Common Name English
BENZGALANTAMINE GLUCONATE [USAN]
Common Name English
Code System Code Type Description
PUBCHEM
155491118
Created by admin on Wed Apr 02 03:26:29 GMT 2025 , Edited by admin on Wed Apr 02 03:26:29 GMT 2025
PRIMARY PUBCHEM
SMS_ID
300000056194
Created by admin on Wed Apr 02 03:26:29 GMT 2025 , Edited by admin on Wed Apr 02 03:26:29 GMT 2025
PRIMARY
USAN
MN-102
Created by admin on Wed Apr 02 03:26:29 GMT 2025 , Edited by admin on Wed Apr 02 03:26:29 GMT 2025
PRIMARY
FDA UNII
LN7PMJ4P57
Created by admin on Wed Apr 02 03:26:29 GMT 2025 , Edited by admin on Wed Apr 02 03:26:29 GMT 2025
PRIMARY
NCI_THESAURUS
C211785
Created by admin on Wed Apr 02 03:26:29 GMT 2025 , Edited by admin on Wed Apr 02 03:26:29 GMT 2025
PRIMARY
CAS
1542321-58-3
Created by admin on Wed Apr 02 03:26:29 GMT 2025 , Edited by admin on Wed Apr 02 03:26:29 GMT 2025
PRIMARY
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