Identification
- Summary
Galantamine is a cholinesterase inhibitor used to manage mild to moderate dementia associated with Alzheimer's Disease.
- Brand Names
- Razadyne
- Generic Name
- Galantamine
- DrugBank Accession Number
- DB00674
- Background
Galantamine is a tertiary alkaloid and reversible, competitive inhibitor of the acetylcholinesterase (AChE) enzyme, which is a widely studied therapeutic target used in the treatment of Alzheimer's disease.1 First characterized in the early 1950s, galantamine is a tertiary alkaloid that was extracted from botanical sources, such as Galanthus nivalis.5 Galantamine was first studied in paralytic and neuropathic conditions, such as myopathies and postpolio paralytic conditions, and for reversal of neuromuscular blockade.7,5 Following the discovery of its AChE-inhibiting properties, the cognitive effects of galantamine were studied in a wide variety of psychiatric disorders such as mild cognitive impairment, cognitive impairment in schizophrenia and bipolar disorder, and autism; however, re-development of the drug for Alzheimer’s disease did not commence until the early 1990s due to difficulties in extraction and synthesis.5 Galantamine blocks the breakdown of acetylcholine in the synaptic cleft, thereby increasing acetylcholine neurotransmission. It also acts as an allosteric modulator of the nicotinic receptor, giving its dual mechanism of action clinical significance.7
The drug was approved by the FDA in 2001 for the treatment of mild to moderate dementia of the Alzheimer's type. As Alzheimer's disease is a progressive neurodegenerative disorder, galantamine is not known to alter the course of the underlying dementing process. Galantamine works to block the enzyme responsible for the breakdown of acetylcholine in the synaptic cleft, thereby enhancing cholinergic neuron function and signalling. Under this hypothesized mechanism of action, the therapeutic effects of galantamine may decrease as the disease progression advances and fewer cholinergic neurons remain functionally intact.10 It is therefore not considered to be a disease-modifying drug.8 Galantamine is marketed under the brand name Razadyne, and is available as oral immediate- and extended-release tablets and solution.10
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Galantamine (DB00674)
- Weight
- Average: 287.3535
Monoisotopic: 287.152143543 - Chemical Formula
- C17H21NO3
- Synonyms
- (-)-Galanthamine
- Galantamina
- Galantamine
- Galanthamine
- External IDs
- NSC-100058
Pharmacology
- Indication
Galantamine is indicated for the treatment of mild to moderate dementia of the Alzheimer’s type.10
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Mild to moderate dementia due to alzheimer's disease •••••••••••• •••••• ••••••• ••••••••••••••• •••••••• ••••••• •••••••••••• Management of Mild to moderate dementia due to alzheimer's disease •••••••••••• •••••• ••••••• ••••••• •••••••••••• Management of Mild dementia of the alzheimer's type •••••••••••• •••••• ••••••• •••••••• •••••••• •••••••• •••••• Management of Moderate dementia of the alzheimer's type •••••••••••• •••••• ••••••• •••••••• •••••••• •••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Galantamine is a competitive and reversible inhibitor of acetylcholinesterase that works to increase acetylcholine levels.10 Galantamine acts both centrally and peripherally to inhibit both muscle and brain acetylcholinesterase, thereby increasing cholinergic tone.5 Galantamine is also a positive allosteric modulator of neuronal nicotinic acetylcholine receptors.3,5 As dementia is a progressive neurodegenerative disease, galatamine has a negligible effect in altering the course of the underlying process of dementia 10 and may exert its therapeutic effectiveness for a short period of time.8 However, galantamine promoted improvements in cognition, global function, activities of daily living, and behavioural symptoms in clinical studies of Alzheimer’s disease.1,7
Galantamine exhibited therapeutic efficacy in studies of vascular dementia and Alzheimer’s disease with cerebrovascular disease.7 In one study, galantamine reversed scopolamine-induced acute anticholinergic syndrome that was characterized by drowsiness, disorientation, and delirium.5
- Mechanism of action
Alzheimer’s disease is characterized by progressive, irreversible degeneration of acetylcholine-producing neurons, cognitive impairment, and the accumulation of neurofibrillary tangles and amyloid plaques.7,8 The cholinergic system plays a critical role in memory, alongside other important neural functions such as attention, learning, stress response, wakefulness and sleep, and sensory information. Studies show that acetylcholine (ACh) is involved in the modulation of acquisition, encoding, consolidation, reconsolidation, extinction, and retrieval of memory. The gradual loss of cholinergic neurons in Alzheimer’s disease (AD) may, therefore, contribute to the memory loss exhibited by AD patients.8
Acetylcholinesterase is secreted by cholinergic neurons to rapidly hydrolyze ACh at the synaptic cleft to release acetate and choline. Choline is later recycled back into the presynaptic cholinergic neuron via reuptake by the high-affinity choline transporter. There is some evidence demonstrating the potential involvement of the acetylcholinesterase enzyme in the formation of amyloid fibrils.8 Galantamine competitively and reversibly inhibits the anticholinesterase enzyme in the CNS (namely in the frontal cortex and hippocampal regions) 3 by binding to the choline-binding site and acyl-binding pocket of the enzyme active site.2 By blocking the breakdown of ACh, galantamine enhances ACh levels in the synaptic cleft.8
Nicotinic acetylcholine receptors (nAChR) in the CNS are mostly expressed at the presynaptic neuronal membrane to control the release of multiple neurotransmitters, such as ACh, glutamate, GABA, dopamine, serotonin, norepinephrine.7,8 Agonists of nAChRs improve performance in cognitive tasks, while antagonists of nAChR impair cognitive processes.8 Some studies show a decrease in the expression and activity of nAChRs in patients with AD, which may explain the reduction in central cholinergic neurotransmission in these patients.3 Galantamine binds to nAChRs at the allosteric site,7,9 leading to a conformational change of the receptor, increased ACh release, and increased activity of neighbouring glutaminergic and serotoninergic neurons.7 The modulation of nAChRs facilitates both excitatory and inhibitory cholinergic transmissions in brain tissues and increases receptor sensitivity. The modulated release of other neurotransmitters by galantamine may also contribute to the upregulation of nAChRs and amelioration of behavioural symptoms in AD.7
Target Actions Organism AAcetylcholinesterase inhibitorHumans ANeuronal acetylcholine receptor subunit alpha-7 allosteric modulatorHumans UMuscle nicotinic acetylcholine receptor allosteric modulatorHumans UCholinesterase inhibitorHumans - Absorption
Over a dose range of 8-32 mg/day, galantamine exhibits a dose-linear pharmacokinetic profile. The oral bioavailability of galantamine ranges from 90-100%. Following oral administration, the Tmax is about 1 hour.10 Following 10 hours of administration, the mean galantamine plasma concentrations were 82–97 µg/L for the 24 mg/day dose and 114–126 µg/L for the 32 mg/day dose.7
- Volume of distribution
The mean volume of distribution is 175 L. About 52.7% of galantamine is distributed to blood cells, the blood to plasma concentration ratio of galantamine is 1.2.10 Galantamine penetrates the blood–brain barrier.5
- Protein binding
The plasma protein binding of galantamine is 18% at therapeutically relevant concentrations.10
- Metabolism
In vitro study findings suggest that about 75% of the drug is metabolized by CYP2D6 and CYP3A4. CYP2D6 promotes O-demethylation of the drug to form O-desmethyl-galantamine and the CYP3A4-mediated pathway forms the galantamine-N-oxide.7 Important metabolic pathways also include N-demethylation, epimerization, and sulfate conjugation.6 Other metabolites include norgalantamine, O-desmethyl-galantamine, O-desmethyl-norgalantamine, epigalantamine and galantaminone, which do not retain clinically significant pharmacology activities.3
Galantamine can also undergo glucuronidation: in one oral radiolabeled drug study in poor and extensive CYP2D6 metabolizers, about 14-24% of the total radioactivity was identified as galantamine glucuronide 8 hours post-dose. O-demethylation by CYP2D6 becomes prominent in patients with who are extensive metabolizers of CYP2D6, but unchanged galatamine (39-77%) and its glucuronide metabolite (14-24%) predominated in the plasma of both poor and extensive metabolizers of CYP2D6 in a radiolabelled drug study.10 The total plasma clearance, or nonrenal clearnace, accounts for 20–25% of drug elimination.7
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- Route of elimination
Renal clearance accounts for about 20–25% of total plasma clearance of the drug in healthy individuals: the elimination of galantamine has been shown to be decreased in subjects with renal impairment.3 Following oral or intravenous administration, approximately 20% of the dose is excreted as unchanged in the urine within 24 h.7 In a radiolabelled drug study, about 95% and 5% of the total radioactivity was recovered in the urine and feces, respectively. Of the dose recovered in the urine, about 32% was in the unchanged parent compound, and 12% was in the glucuronide form.10
- Half-life
Galantamine has a terminal half-life of about 7 hours.10
- Clearance
The renal clearance is 65 mL/min and the total plasma clearance is about 300 mL/min.7
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral LD50 of the active ingredient, galantamine hydrobromide, in rats is 75 mg/kg.12 Symptoms of overdose are expected to be similar to those of cholinomimetics, which involve the central nervous system, the parasympathetic nervous system, and the neuromuscular junction. Effects of a cholinergic crisis include severe nausea, vomiting, gastrointestinal cramping, salivation, lacrimation, urination, defecation, sweating, bradycardia, hypotension, respiratory depression, collapse, and convulsions. Muscle weakness or fasciculations may also occur, with respiratory muscle weakness having the potential to bring fatal results. In one patient who consumed an oral daily dose of 32 mg developed bradycardia, QT prolongation, ventricular tachycardia and torsades de pointes accompanied by a brief loss of consciousness. In one patient with a history of hallucinations who consumed a daily dose of 24 mg galantamine, hallucinations requiring hospitalization occurred. A patient who ingested 160 mg of galantamine from an oral solution developed sweating, vomiting, bradycardia, and near-syncope one hour following consumption.10
As in any case of overdose, general supportive measures should be initiated. Tertiary anticholinergics such as intravenous atropine may be used to reverse the cholinergic effects of galantamine. The recommended initial dose of atropine intravenously administered for galantamine overdose ranges from 0.5 to 1.0 mg. It is not known whether galantamine can be removed by dialysis.10
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*4 Not Available C allele Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*6 Not Available 1707delT Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 3A4 CYP3A4*20 Not Available 1461_1462insA Effect Inferred Poor drug metabolizer. Details Cytochrome P450 3A4 CYP3A4*26 Not Available 802C>T Effect Inferred Poor drug metabolizer. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Galantamine can be increased when it is combined with Abametapir. Abatacept The metabolism of Galantamine can be increased when combined with Abatacept. Abiraterone The metabolism of Galantamine can be decreased when combined with Abiraterone. Acebutolol Galantamine may increase the bradycardic activities of Acebutolol. Acetaminophen The metabolism of Galantamine can be decreased when combined with Acetaminophen. - Food Interactions
- Take with food. Food delays the rate of absorption but not the extent.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Galantamine hydrobromide MJ4PTD2VVW 1953-04-4 QORVDGQLPPAFRS-XPSHAMGMSA-N - Product Images
- International/Other Brands
- Lycoremine / Nivalin / Reminyl
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Galantamine ER Capsule, extended release 16 mg Oral Sanis Health Inc 2016-01-11 Not applicable Canada 
Galantamine ER Capsule, extended release 16 mg Oral Pro Doc Limitee 2013-12-03 2023-07-10 Canada Galantamine ER Capsule, extended release 8 mg Oral Sanis Health Inc 2016-01-11 Not applicable Canada Galantamine ER Capsule, extended release 8 mg Oral Pro Doc Limitee 2013-12-03 2023-07-10 Canada Galantamine ER Capsule, extended release 24 mg Oral Sanis Health Inc 2016-01-11 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-galantamine Tablet 4 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-galantamine Tablet 12 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-galantamine Tablet 8 mg Oral Apotex Corporation Not applicable Not applicable Canada Auro-galantamine ER Capsule, extended release 8 mg Oral Auro Pharma Inc 2014-06-12 Not applicable Canada Auro-galantamine ER Capsule, extended release 24 mg Oral Auro Pharma Inc 2014-06-12 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image GALNORA 8MG + 16MG HKP RET Galantamine hydrobromide (8 mg) + Galantamine hydrobromide (16 mg) Capsule, extended release Oral 2015-04-01 Not applicable Germany 
GALNORA 8MG + 16MG HKP RET Galantamine hydrobromide (8 mg) + Galantamine hydrobromide (16 mg) Capsule, extended release Oral 2015-04-01 Not applicable Germany
Categories
- ATC Codes
- N06DA04 — Galantamine
- Drug Categories
- Alkaloids
- Amaryllidaceae Alkaloids
- Anti-Dementia Drugs
- Autonomic Agents
- Benzazepines
- Bradycardia-Causing Agents
- Central Nervous System Agents
- Cholinergic Agents
- Cholinesterase Inhibitors
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Nervous System
- Neurotransmitter Agents
- Nootropic Agents
- P-glycoprotein inhibitors
- Parasympathomemetic (Cholinergic) Agents
- Parasympathomimetics
- Peripheral Nervous System Agents
- Potential QTc-Prolonging Agents
- Psychoanaleptics
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Amaryllidaceae alkaloids
- Sub Class
- Galanthamine-type amaryllidaceae alkaloids
- Direct Parent
- Galanthamine-type amaryllidaceae alkaloids
- Alternative Parents
- Benzazepines / Coumarans / Anisoles / Azepines / Aralkylamines / Alkyl aryl ethers / Trialkylamines / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds show 2 more
- Substituents
- Alcohol / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzazepine / Benzenoid show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amino compound, organic heterotetracyclic compound, benzazepine alkaloid, benzazepine alkaloid fundamental parent (CHEBI:42944) / Isoquinoline alkaloids (C08526)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0D3Q044KCA
- CAS number
- 357-70-0
- InChI Key
- ASUTZQLVASHGKV-JDFRZJQESA-N
- InChI
- InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1
- IUPAC Name
- (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-ol
- SMILES
- [H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3
References
- Synthesis Reference
Vijaya Bolugoddu, Sanjay Shukla, Mukunda Jambula, Rajeshwar Sagyam, Ramchandra Pingili, Ananda Thirunavakarasu, "Preparation of (-)-galantamine hydrobromide." U.S. Patent US20060009640, issued January 12, 2006.
US20060009640- General References
- Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [Article]
- Greenblatt HM, Kryger G, Lewis T, Silman I, Sussman JL: Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3 A resolution. FEBS Lett. 1999 Dec 17;463(3):321-6. [Article]
- Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [Article]
- Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [Article]
- Mucke HA: The case of galantamine: repurposing and late blooming of a cholinergic drug. Future Sci OA. 2015 Sep 3;1(4):FSO73. doi: 10.4155/fso.15.73. eCollection 2015 Nov. [Article]
- Mannens GS, Snel CA, Hendrickx J, Verhaeghe T, Le Jeune L, Bode W, van Beijsterveldt L, Lavrijsen K, Leempoels J, Van Osselaer N, Van Peer A, Meuldermans W: The metabolism and excretion of galantamine in rats, dogs, and humans. Drug Metab Dispos. 2002 May;30(5):553-63. doi: 10.1124/dmd.30.5.553. [Article]
- Farlow MR: Clinical pharmacokinetics of galantamine. Clin Pharmacokinet. 2003;42(15):1383-92. doi: 10.2165/00003088-200342150-00005. [Article]
- Ferreira-Vieira TH, Guimaraes IM, Silva FR, Ribeiro FM: Alzheimer's disease: Targeting the Cholinergic System. Curr Neuropharmacol. 2016;14(1):101-15. doi: 10.2174/1570159x13666150716165726. [Article]
- Akk G, Steinbach JH: Galantamine activates muscle-type nicotinic acetylcholine receptors without binding to the acetylcholine-binding site. J Neurosci. 2005 Feb 23;25(8):1992-2001. doi: 10.1523/JNEUROSCI.4985-04.2005. [Article]
- FDA Approved Drug Products: RAZADYNE (galantamine hydrobromide), for oral use [Link]
- DailyMed Label: RAZADYNE - galantamine hydrobromide CAPSULE, EXTENDED RELEASE RAZADYNE - galantamine hydrobromide TABLET, FILM COATED [Link]
- Fisher Scientific: Galantamine hydrobromide MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0014812
- KEGG Drug
- D04292
- KEGG Compound
- C08526
- PubChem Compound
- 9651
- PubChem Substance
- 46505659
- ChemSpider
- 9272
- BindingDB
- 10404
- 4637
- ChEBI
- 42944
- ChEMBL
- CHEMBL659
- ZINC
- ZINC000000491073
- Therapeutic Targets Database
- DAP000559
- PharmGKB
- PA449726
- PDBe Ligand
- GNT
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Galantamine
- PDB Entries
- 1dx6 / 1qti / 1w6r / 1w76 / 2ph9 / 4ey6
- FDA label
- Download (278 KB)
- MSDS
- Download (28.4 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Abdominal Obesity Metabolic Syndrome 1 4 Completed Treatment Alzheimer's Disease (AD) 5 4 Completed Treatment Attention Deficit Hyperactivity Disorder (ADHD) 1 4 Completed Treatment Bipolar Disorder (BD) 2 4 Completed Treatment Dementia 1
Pharmacoeconomics
- Manufacturers
- Barr laboratories inc
- Impax laboratories inc
- Watson laboratories inc
- Ortho mcneil janssen pharmaceuticals inc
- Roxane laboratories inc
- Ortho mcneil janssen pharmaceutical inc
- Actavis elizabeth llc
- Beijing yabao biopharmaceutical co ltd
- Dr reddys laboratories ltd
- Mylan pharmaceuticals inc
- Sandoz inc
- Teva pharmaceuticals usa
- Packagers
- Alphapharm Party Ltd.
- Barr Pharmaceuticals
- Cardinal Health
- DispenseXpress Inc.
- Doctor Reddys Laboratories Ltd.
- Global Pharmaceuticals
- Heartland Repack Services LLC
- Impax Laboratories Inc.
- Janssen-Ortho Inc.
- Kaiser Foundation Hospital
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- Patriot Pharmaceuticals
- Physician Partners Ltd.
- Physicians Total Care Inc.
- Rebel Distributors Corp.
- Resource Optimization and Innovation LLC
- Roxane Labs
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Vangard Labs Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet, effervescent Tablet Oral 12 mg/1 Tablet Oral 4 mg/1 Tablet Oral 8 mg/1 Tablet, film coated Oral 12 mg/1 Tablet, film coated Oral 4 mg/1 Tablet, film coated Oral 8 mg/1 Capsule, extended release Oral 24 mg/1 Capsule, extended release Oral 8 mg/1 Capsule, extended release Oral 8 mg Capsule, extended release Oral Capsule Oral 16.000 mg Capsule, extended release Oral Capsule, extended release Oral 24 mg Capsule, extended release Oral 16 mg/1 Solution Oral 4 mg/1mL Capsule, extended release Oral 8 MG/16MG Solution Oral 4 mg/ml Solution Oral 512.400 mg Tablet, film coated Oral Tablet, film coated Oral 12 MG Tablet, film coated Oral 8 MG Tablet Oral 12 mg Tablet Oral 4 mg Tablet Oral 8 mg Tablet, film coated Oral 4 MG Capsule Oral 10.250 mg Capsule, coated, extended release Oral 16 MG Capsule, extended release Oral 16 mg Capsule, coated, extended release Oral 24 MG Capsule, coated, extended release Oral 8 MG Capsule, coated pellets Oral Solution Oral 400 mg - Prices
Unit description Cost Unit Galantamine Hydrobromide 30 16 mg 24 Hour Capsule Bottle 198.58USD bottle Galantamine Hydrobromide 30 8 mg 24 Hour Capsule Bottle 198.58USD bottle Razadyne 12 mg tablet 8.3USD tablet Razadyne 4 mg tablet 5.36USD tablet Razadyne 8 mg tablet 3.66USD tablet Galantamine hbr 12 mg tablet 3.18USD tablet Galantamine hbr 4 mg tablet 3.18USD tablet Galantamine hbr 8 mg tablet 3.18USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2358062 No 2006-12-19 2019-12-20 Canada CA2310926 No 2001-11-20 2017-06-06 Canada US6358527 No 2002-03-19 2017-06-06 US 
US6099863 No 2000-08-08 2017-06-06 US US7160559 No 2007-01-09 2019-12-20 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP 1.16 Chemaxon pKa (Strongest Acidic) 14.81 Chemaxon pKa (Strongest Basic) 8.58 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 41.93 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 82.3 m3·mol-1 Chemaxon Polarizability 31.5 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9959 Caco-2 permeable + 0.8259 P-glycoprotein substrate Substrate 0.8976 P-glycoprotein inhibitor I Inhibitor 0.6069 P-glycoprotein inhibitor II Non-inhibitor 0.9443 Renal organic cation transporter Inhibitor 0.5728 CYP450 2C9 substrate Non-substrate 0.8072 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.7408 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.5414 CYP450 2C19 inhibitor Non-inhibitor 0.8301 CYP450 3A4 inhibitor Non-inhibitor 0.8832 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9439 Ames test Non AMES toxic 0.7995 Carcinogenicity Non-carcinogens 0.9055 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7790 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8023 hERG inhibition (predictor II) Non-inhibitor 0.7424
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.0043821 predictedDarkChem Lite v0.1.0 [M-H]- 177.0595821 predictedDarkChem Lite v0.1.0 [M-H]- 176.9950821 predictedDarkChem Lite v0.1.0 [M-H]- 168.11557 predictedDeepCCS 1.0 (2019) [M+H]+ 177.3969821 predictedDarkChem Lite v0.1.0 [M+H]+ 176.8565821 predictedDarkChem Lite v0.1.0 [M+H]+ 177.1200821 predictedDarkChem Lite v0.1.0 [M+H]+ 170.47357 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.9041821 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.7805821 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.9176821 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.44682 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine hydrolase activity
- Specific Function
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name
- ACHE
- Uniprot ID
- P22303
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
References
- Tonkopii VD, Prozorovskii VB, Suslova IM: [Interaction of reversible inhibitors with the catalytic centers and allosteric sites of cholinesterases]. Biull Eksp Biol Med. 1976 Aug;82(8):947-50. [Article]
- Greenblatt HM, Kryger G, Lewis T, Silman I, Sussman JL: Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3 A resolution. FEBS Lett. 1999 Dec 17;463(3):321-6. [Article]
- Guillou C, Mary A, Renko DZ, Gras E, Thal C: Potent acetylcholinesterase inhibitors: design, synthesis and structure-activity relationships of alkylene linked bis-galanthamine and galanthamine-galanthaminium salts. Bioorg Med Chem Lett. 2000 Apr 3;10(7):637-9. [Article]
- Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [Article]
- Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [Article]
- Woodruff-Pak DS, Vogel RW 3rd, Wenk GL: Galantamine: effect on nicotinic receptor binding, acetylcholinesterase inhibition, and learning. Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):2089-94. Epub 2001 Feb 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Allosteric modulator
- Curator comments
- Galantamine binding site is different from the ACh binding site.
- General Function
- Toxic substance binding
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
- Gene Name
- CHRNA7
- Uniprot ID
- P36544
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-7
- Molecular Weight
- 56448.925 Da
References
- Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [Article]
- Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [Article]
- Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [Article]
- Ludwig J, Hoffle-Maas A, Samochocki M, Luttmann E, Albuquerque EX, Fels G, Maelicke A: Localization by site-directed mutagenesis of a galantamine binding site on alpha7 nicotinic acetylcholine receptor extracellular domain. J Recept Signal Transduct Res. 2010 Dec;30(6):469-83. doi: 10.3109/10799893.2010.505239. Epub 2010 Nov 9. [Article]
- Woodruff-Pak DS, Vogel RW 3rd, Wenk GL: Galantamine: effect on nicotinic receptor binding, acetylcholinesterase inhibition, and learning. Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):2089-94. Epub 2001 Feb 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Allosteric modulator
- General Function
- Not Available
- Specific Function
- Extracellular ligand-gated ion channel activity
- Gene Name
- Not Available
- Uniprot ID
- A9X444
- Uniprot Name
- Muscle nicotinic acetylcholine receptor
- Molecular Weight
- 10252.8 Da
References
- Akk G, Steinbach JH: Galantamine activates muscle-type nicotinic acetylcholine receptors without binding to the acetylcholine-binding site. J Neurosci. 2005 Feb 23;25(8):1992-2001. doi: 10.1523/JNEUROSCI.4985-04.2005. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- The IC50 value is 18.6 umol/L (Lilienfeld, 2002).
- General Function
- Identical protein binding
- Specific Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Svoboda Z, Kvetina J, Kunesova G, Herink J, Bajgar J, Bartosova L, Zivny P, Palicka V: Effect of galantamine on acetylcholinesterase and butyrylcholinesterase activities in the presence of L-carnitine in rat selected brain and peripheral tissues. Neuro Endocrinol Lett. 2006 Dec;27 Suppl 2:183-6. [Article]
- Giacobini E: Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease? Drugs Aging. 2001;18(12):891-8. [Article]
- Wilkinson DG: Galantamine: a new treatment for Alzheimer's disease. Expert Rev Neurother. 2001 Nov;1(2):153-9. doi: 10.1586/14737175.1.2.153. [Article]
- Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Jann MW, Shirley KL, Small GW: Clinical pharmacokinetics and pharmacodynamics of cholinesterase inhibitors. Clin Pharmacokinet. 2002;41(10):719-39. doi: 10.2165/00003088-200241100-00003. [Article]
- Farlow MR: Clinical pharmacokinetics of galantamine. Clin Pharmacokinet. 2003;42(15):1383-92. doi: 10.2165/00003088-200342150-00005. [Article]
- Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [Article]
- Piotrovsky V, Van Peer A, Van Osselaer N, Armstrong M, Aerssens J: Galantamine population pharmacokinetics in patients with Alzheimer's disease: modeling and simulations. J Clin Pharmacol. 2003 May;43(5):514-23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Jann MW, Shirley KL, Small GW: Clinical pharmacokinetics and pharmacodynamics of cholinesterase inhibitors. Clin Pharmacokinet. 2002;41(10):719-39. doi: 10.2165/00003088-200241100-00003. [Article]
- Farlow MR: Clinical pharmacokinetics of galantamine. Clin Pharmacokinet. 2003;42(15):1383-92. doi: 10.2165/00003088-200342150-00005. [Article]
- Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [Article]
- Piotrovsky V, Van Peer A, Van Osselaer N, Armstrong M, Aerssens J: Galantamine population pharmacokinetics in patients with Alzheimer's disease: modeling and simulations. J Clin Pharmacol. 2003 May;43(5):514-23. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Namanja HA, Emmert D, Pires MM, Hrycyna CA, Chmielewski J: Inhibition of human P-glycoprotein transport and substrate binding using a galantamine dimer. Biochem Biophys Res Commun. 2009 Oct 30;388(4):672-6. doi: 10.1016/j.bbrc.2009.08.056. Epub 2009 Aug 14. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54