Identification

Name
Galantamine
Accession Number
DB00674  (APRD00206, EXPT01628)
Type
Small Molecule
Groups
Approved
Description

A benzazepine derived from norbelladine. It is found in galanthus and other amaryllidaceae. Galantamine is a cholinesterase inhibitor that has been used to reverse the muscular effects of gallamine triethiodide and tubocurarine, and has been studied as a treatment for Alzheimer's disease and other central nervous system disorders.

Structure
Thumb
Synonyms
  • (-)-Galanthamine
  • Galantamina
  • Galantamine
  • Galanthamine
External IDs
NSC-100058
Product Ingredients
IngredientUNIICASInChI Key
Galantamine hydrobromideMJ4PTD2VVW1953-04-4QORVDGQLPPAFRS-XPSHAMGMSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Galantamine ERCapsule, extended release8 mgOralPro Doc Limitee2013-12-03Not applicableCanada
Galantamine ERCapsule, extended release24 mgOralPro Doc Limitee2013-12-03Not applicableCanada
Galantamine ERCapsule, extended release16 mgOralSanis Health Inc2016-01-11Not applicableCanada
Galantamine ERCapsule, extended release16 mgOralPro Doc Limitee2013-12-03Not applicableCanada
Galantamine ERCapsule, extended release8 mgOralSanis Health Inc2016-01-11Not applicableCanada
Galantamine ERCapsule, extended release24 mgOralSanis Health Inc2016-01-11Not applicableCanada
Galantamine HydrobromideTablet, film coated8 mg/1OralPatriot Pharmaceuticals, LLC2001-02-28Not applicableUs
Galantamine HydrobromideTablet, film coated12 mg/1OralAvera McKennan Hospital2015-09-022018-05-25Us
Galantamine HydrobromideTablet, film coated8 mg/1OralYabao Pharmaceutical Co., Ltd. Beijing2001-03-01Not applicableUs
Galantamine HydrobromideCapsule, extended release8 mg/1OralPatriot Pharmaceuticals, LLC2004-12-22Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-galantamineTablet8 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-galantamineTablet12 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-galantamineTablet4 mgOralApotex CorporationNot applicableNot applicableCanada
Auro-galantamine ERCapsule, extended release16 mgOralAuro Pharma Inc2014-06-12Not applicableCanada
Auro-galantamine ERCapsule, extended release8 mgOralAuro Pharma Inc2014-06-12Not applicableCanada
Auro-galantamine ERCapsule, extended release24 mgOralAuro Pharma Inc2014-06-12Not applicableCanada
GalantamineCapsule, extended release8 mg/1OralTeva2008-10-142017-10-31Us00555 1020 01 nlmimage10 d02b687b
GalantamineTablet, film coated12 mg/1OralTeva2009-07-092009-07-10Us
GalantamineTablet, film coated4 mg/1OralZydus Pharmaceuticals Usa, Inc.2011-10-10Not applicableUs
GalantamineTablet, film coated12 mg/1OralRising Health, Llc2011-03-29Not applicableUs
International/Other Brands
Lycoremine / Nivalin / Reminyl
Categories
UNII
0D3Q044KCA
CAS number
357-70-0
Weight
Average: 287.3535
Monoisotopic: 287.152143543
Chemical Formula
C17H21NO3
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[8.6.1.0¹,¹².0⁶,¹⁷]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

Pharmacology

Indication

For the treatment of mild to moderate dementia of the Alzheimer's type. Has also been investigated in patients with mild cognitive impairment who did not meet the diagnostic criteria for Alzheimer's disease.

Associated Conditions
Pharmacodynamics

Galantamine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor. It is indicated for the treatment of mild to moderate dementia of the Alzheimer's type. An early pathophysiological feature of Alzheimer's disease that is associated with memory loss and cognitive deficits is a deficiency of acetylcholine as a result of selective loss of cholinergic neurons in the cerebral cortex, nucleus basalis, and hippocampus. Galantamine 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 proposed mechanism of action is correct, Galantamine's effect may lessen as the disease progresses and fewer cholinergic neurons remain functionally intact. There is no evidence that Galantamine alters the course of the underlying dementing process.

Mechanism of action

Galantamine is a phenanthrene alkaloid and a reversible, competitive acetylcholinesterase inhibitor. It is not structurally related to other acetylcholinesterase inhibitors. Galantamine's proposed mechanism of action involves the reversible inhibition of acetylcholinesterase, which prevents the hydrolysis of acetycholine, leading to an increased concentration of acetylcholine at cholinergic synapses. Galantamine also binds allosterically with nicotinic acetylcholine receptors and may possibly potentiate the action of agonists (such as acetylcholine) at these receptors.

TargetActionsOrganism
AAcetylcholinesterase
inhibitor
Human
UAcetylcholine receptor subunit alpha
allosteric modulator
Human
UAcetylcholine receptor subunit beta
allosteric modulator
Human
UAcetylcholine receptor subunit delta
allosteric modulator
Human
UAcetylcholine receptor subunit gamma
allosteric modulator
Human
UAcetylcholine receptor subunit epsilon
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-2
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-3
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-4
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-5
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-6
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-7
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-9
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit alpha-10
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit beta-2
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit beta-3
allosteric modulator
Human
UNeuronal acetylcholine receptor subunit beta-4
allosteric modulator
Human
UCholinesterase
inhibitor
Human
Absorption
Not Available
Volume of distribution
  • 175 L
Protein binding

18%

Metabolism
Route of elimination

Galantamine is metabolized by hepatic cytochrome P450 enzymes, glucuronidated, and excreted unchanged in the urine.

Half life

7 hours

Clearance
  • 300 mL/min [After IV. or oral administration]
Toxicity

LD50=75 mg/kg (rat)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*4Not AvailableC alleleEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 3A4CYP3A4*20Not Available1461_1462insAEffect InferredPoor drug metabolizer.Details
Cytochrome P450 3A4CYP3A4*26Not Available802C>TEffect InferredPoor drug metabolizer.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Galantamine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Galantamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Galantamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Galantamine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Galantamine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Galantamine.
6-Deoxyerythronolide BThe metabolism of Galantamine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Galantamine.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Galantamine.
AbacavirGalantamine may decrease the excretion rate of Abacavir which could result in a higher serum level.
Food Interactions
  • Take with food.

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
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:10606746]
  3. 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. [PubMed:11172080]
  4. Birks J: Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst Rev. 2006 Jan 25;(1):CD005593. [PubMed:16437532]
  5. 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. [PubMed:12177686]
  6. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
External Links
Human Metabolome Database
HMDB0014812
KEGG Drug
D04292
KEGG Compound
C08526
PubChem Compound
9651
PubChem Substance
46505659
ChemSpider
9272
BindingDB
10404
ChEBI
42944
ChEMBL
CHEMBL659
Therapeutic Targets Database
DAP000559
PharmGKB
PA449726
HET
GNT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Galantamine
ATC Codes
N06DA04 — Galantamine
AHFS Codes
  • 12:04.00 — Parasympathomemetic (Cholinergic) Agents
PDB Entries
1dx6 / 1qti / 1w6r / 1w76 / 2ph9 / 4ey6
FDA label
Download (278 KB)
MSDS
Download (28.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableAlzheimer's Disease (AD)1
1CompletedNot AvailableHealthy Volunteers2
1CompletedScreeningMemory1
1CompletedTreatmentAlzheimer's Disease (AD)1
1CompletedTreatmentFasting1
1CompletedTreatmentFed1
1CompletedTreatmentPharmacokinetics1
1CompletedTreatmentSmoking / Tobacco Withdrawal1
1Not Yet RecruitingTreatmentRefractory Neuroblastoma / Relapsed Neuroblastoma1
1RecruitingBasic SciencePostural Tachycardia Syndrome1
1TerminatedTreatmentLeukemias / Myelodysplastic Syndromes1
1WithdrawnTreatmentInsulin Sensitivity / Oxidative Stress1
1, 2RecruitingTreatmentBMI >30 kg/m21
2Active Not RecruitingPreventionSchizophrenic Disorders1
2Active Not RecruitingTreatmentSickle Cell Disorders1
2CompletedTreatmentDependence, Cocaine1
2CompletedTreatmentFrontotemporal Dementia / Pick Complex1
2CompletedTreatmentNicotine Addiction1
2CompletedTreatmentPeripheral T-Cell Lymphoma (PTCL)1
2CompletedTreatmentSchizophrenic Disorders1
2Not Yet RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Large B-cell Lymphoma / Refractory CD19+ B-cell Pediatric ALL / Refractory Diffuse Large B Cell Lymphoma / Refractory Large B-cell Lymphoma / Relapsed CD19+ B-cell Pediatric ALL / Relapsed Large B-cell Lymphoma1
2RecruitingTreatmentCognitive Impairments / Strokes1
2RecruitingTreatmentDiffuse Sclerosis Systemic / Interstitial Lung Disease (ILD) / Pulmonary Hypertension (PH) / Sclerosis, Progressive Systemic1
2RecruitingTreatmentDouble-hit Lymphoma / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Peripheral T Cell Lymphoma (PTCL)1
2RecruitingTreatmentHIV Associated Cognitive Motor Complex1
2RecruitingTreatmentTobacco Use Disorders1
2TerminatedTreatmentPosttraumatic Stress Disorders / Traumatic Brain Injury (TBI)1
2TerminatedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2, 3CompletedTreatmentSchizophrenic Disorders1
2, 3RecruitingNot AvailableDementia, Vascular / Mild Cognitive Disorder (Vascular) / Mild Cognitive Impairment (Vascular)1
3CompletedTreatmentAlzheimer's Disease (AD)6
3CompletedTreatmentAlzheimer's Disease (AD) / Brain Diseases / Dementias / Psychiatric Disorder NOS1
3CompletedTreatmentAlzheimer's Disease (AD) / Dementia, Vascular1
3CompletedTreatmentAlzheimer's Disease (AD) / Dementias9
3CompletedTreatmentAutism, Early Infantile1
3CompletedTreatmentBrain Diseases / Cognition Disorder / Nervous System Diseases / Psychiatric Disorder NOS1
3CompletedTreatmentChronic Lymphocytic Leukaemia (CLL)1
3CompletedTreatmentDementia, Vascular1
3CompletedTreatmentDepression, Bipolar / Major Depressive Disorder (MDD) / Schizoaffective Disorders1
3CompletedTreatmentDiffuse Lewy Body Disease1
3RecruitingTreatmentAcute Lymphoblastic Leukemia, Pediatric1
3TerminatedTreatmentAlzheimer's Disease (AD)1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentLymphoma, Large-Cell, Diffuse1
4CompletedNot AvailableAlzheimer's Disease (AD)2
4CompletedNot AvailableAlzheimer's Disease (AD) / Dementia, Vascular / Dementias1
4CompletedNot AvailableAlzheimer's Disease (AD) / Dementias / Galantamine1
4CompletedTreatmentAbdominal Obesity Metabolic Syndrome1
4CompletedTreatmentAlzheimer's Disease (AD)4
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentCerebrovascular Accidents1
4CompletedTreatmentDementias1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders2
4CompletedTreatmentTardive Dyskinesia1
4TerminatedBasic ScienceAlzheimer's Disease (AD)1
4TerminatedTreatmentAlzheimer's Disease (AD)1
4TerminatedTreatmentDepression1
4TerminatedTreatmentGilles de la Tourette's Syndrome / Motor Tic Disorder / Vocal Tic Disorder1
4TerminatedTreatmentPsychotic Disorder NOS / Schizophrenic Disorders1
4Unknown StatusTreatmentAlzheimer's Disease (AD)1
4Unknown StatusTreatmentHead Trauma,Closed / Post-Traumatic Headaches / Retention Disorders, Cognitive1
Not AvailableCompletedNot AvailableBiomarkers, Pharmacological1
Not AvailableCompletedNot AvailableDiffuse Lewy Body Disease1
Not AvailableCompletedBasic ScienceBasic Science Study of the Mechanisms of Attentional Enhancement by Compounds Acting on the Nicotinic Receptor1
Not AvailableCompletedTreatmentAddictions1
Not AvailableCompletedTreatmentAphasia / Strokes1
Not AvailableCompletedTreatmentChronic Schizophrenia1
Not AvailableCompletedTreatmentCocaine Abuse1
Not AvailableCompletedTreatmentDementias1
Not AvailableCompletedTreatmentNicotine Dependence1
Not AvailableTerminatedTreatmentAlzheimer's Disease (AD) / Dementias1
Not AvailableUnknown StatusPreventionParkinson's Disease (PD)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
FormRouteStrength
TabletOral12 mg/1
TabletOral4 mg/1
TabletOral8 mg/1
Tablet, film coatedOral12 mg/1
Tablet, film coatedOral4 mg/1
Tablet, film coatedOral8 mg/1
Capsule, extended releaseOral24 mg/1
Capsule, extended releaseOral8 mg/1
SolutionOral4 mg/1mL
Capsule, extended releaseOral16 mg
Capsule, extended releaseOral24 mg
Capsule, extended releaseOral8 mg
Capsule, extended releaseOral16 mg/1
TabletOral12 mg
TabletOral4 mg
TabletOral8 mg
Prices
Unit descriptionCostUnit
Galantamine Hydrobromide 30 16 mg 24 Hour Capsule Bottle198.58USD bottle
Galantamine Hydrobromide 30 8 mg 24 Hour Capsule Bottle198.58USD bottle
Razadyne 12 mg tablet8.3USD tablet
Razadyne 4 mg tablet5.36USD tablet
Razadyne 8 mg tablet3.66USD tablet
Galantamine hbr 12 mg tablet3.18USD tablet
Galantamine hbr 4 mg tablet3.18USD tablet
Galantamine hbr 8 mg tablet3.18USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2358062No2006-12-192019-12-20Canada
CA2310926No2001-11-202017-06-06Canada
US6358527No2002-03-192017-06-06Us
US6099863No2000-08-082017-06-06Us
US7160559No2007-01-092019-12-20Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)269-270 °C (HBr salt)Not Available
water solubility10 mg/mL (HBr salt)Not Available
logP1.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.7 mg/mLALOGPS
logP1.39ALOGPS
logP1.16ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)14.81ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.3 m3·mol-1ChemAxon
Polarizability31.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9959
Caco-2 permeable+0.8259
P-glycoprotein substrateSubstrate0.8976
P-glycoprotein inhibitor IInhibitor0.6069
P-glycoprotein inhibitor IINon-inhibitor0.9443
Renal organic cation transporterInhibitor0.5728
CYP450 2C9 substrateNon-substrate0.8072
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7408
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.5414
CYP450 2C19 inhibitorNon-inhibitor0.8301
CYP450 3A4 inhibitorNon-inhibitor0.8832
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9439
Ames testNon AMES toxic0.7995
CarcinogenicityNon-carcinogens0.9055
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7790 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8023
hERG inhibition (predictor II)Non-inhibitor0.7424
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-000l-5980000000-928ad889466b6a2b3827
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0390000000-f4f443a7f842d92dec39

Taxonomy

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
Galanthamine-type amaryllidaceae alkaloid / Benzazepine / Coumaran / Anisole / Alkyl aryl ether / Azepine / Aralkylamine / Benzenoid / Secondary alcohol / Tertiary amine
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)

Targets

Details
1. Acetylcholinesterase
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:1026294]
  2. 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. [PubMed:10606746]
  3. 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. [PubMed:10762042]
  4. Blesa R: Galantamine: therapeutic effects beyond cognition. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:28-34. [PubMed:10971049]
  5. Stahl SM: The new cholinesterase inhibitors for Alzheimer's disease, Part 1: their similarities are different. J Clin Psychiatry. 2000 Oct;61(10):710-1. [PubMed:11078030]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. 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. [PubMed:12177686]
  8. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  9. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  10. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  11. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  12. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
  13. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Ion channel activity
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.
Gene Name
CHRNA1
Uniprot ID
P02708
Uniprot Name
Acetylcholine receptor subunit alpha
Molecular Weight
54545.235 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Ligand-gated ion channel activity
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.
Gene Name
CHRNB1
Uniprot ID
P11230
Uniprot Name
Acetylcholine receptor subunit beta
Molecular Weight
56697.9 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Acetylcholine-activated cation-selective channel activity
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.
Gene Name
CHRND
Uniprot ID
Q07001
Uniprot Name
Acetylcholine receptor subunit delta
Molecular Weight
58894.55 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Channel activity
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.
Gene Name
CHRNG
Uniprot ID
P07510
Uniprot Name
Acetylcholine receptor subunit gamma
Molecular Weight
57882.8 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Cation transmembrane transporter activity
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.
Gene Name
CHRNE
Uniprot ID
Q04844
Uniprot Name
Acetylcholine receptor subunit epsilon
Molecular Weight
54696.54 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Drug 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.
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Ligand-gated ion channel activity
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.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Ligand-gated ion channel activity
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 permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Ligand-gated ion channel activity
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.
Gene Name
CHRNA5
Uniprot ID
P30532
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-5
Molecular Weight
53053.965 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Acetylcholine-activated cation-selective channel activity
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.
Gene Name
CHRNA6
Uniprot ID
Q15825
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-6
Molecular Weight
56897.745 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
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
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Calcium channel activity
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasm...
Gene Name
CHRNA9
Uniprot ID
Q9UGM1
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-9
Molecular Weight
54806.63 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Receptor binding
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an i...
Gene Name
CHRNA10
Uniprot ID
Q9GZZ6
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-10
Molecular Weight
49704.295 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Ligand-gated ion channel activity
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 permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Drug 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.
Gene Name
CHRNB3
Uniprot ID
Q05901
Uniprot Name
Neuronal acetylcholine receptor subunit beta-3
Molecular Weight
52728.215 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Allosteric modulator
General Function
Ligand-gated ion channel activity
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.
Gene Name
CHRNB4
Uniprot ID
P30926
Uniprot Name
Neuronal acetylcholine receptor subunit beta-4
Molecular Weight
56378.985 Da
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124]
  2. 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. [PubMed:12177686]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632]
  4. Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048]
  5. Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: Drug Class Review: Alzheimer's Drugs: Final Report [Internet] . [PubMed:20480924]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  1. 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. [PubMed:17159811]
  2. Giacobini E: Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease? Drugs Aging. 2001;18(12):891-8. [PubMed:11888344]
  3. 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. [PubMed:19811027]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 17:06