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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:09 UTC
HMDB IDHMDB14812
Secondary Accession NumbersNone
Metabolite Identification
Common NameGalantamine
DescriptionA 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. [PubChem]
Structure
Thumb
Synonyms
ValueSource
(-)-GALANTHAMINEChEBI
GalanthamineHMDB
Galanthamine hydrobromideHMDB
Chemical FormulaC17H21NO3
Average Molecular Weight287.3535
Monoisotopic Molecular Weight287.152143543
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
Traditional Namegalantamine
CAS Registry Number357-70-0
SMILES
[H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3
InChI Identifier
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
InChI KeyInChIKey=ASUTZQLVASHGKV-JDFRZJQESA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassGalanthamine-type amaryllidaceae alkaloids
Direct ParentGalanthamine-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Galanthamine-type amaryllidaceae alkaloid
  • Benzazepine
  • Benzofuran
  • Anisole
  • Aralkylamine
  • Azepine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Cholinesterase Inhibitors
  • Nootropic Agents
  • Parasympathomimetics
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point269 - 270 °C (hydrogen bromide salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility1.70e+00 g/LNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-000l-5980000000-928ad889466b6a2b3827View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00674
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00674
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00674
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9272
KEGG Compound IDC08526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGalantamine
NuGOwiki LinkHMDB14812
Metagene LinkHMDB14812
METLIN IDNot Available
PubChem Compound9651
PDB IDGNT
ChEBI ID5264
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [10606746 ]
  2. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [12137632 ]
  3. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [11129124 ]
  4. Birks J: Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst Rev. 2006 Jan 25;(1):CD005593. [16437532 ]
  5. 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. [11172080 ]

Enzymes

General function:
Involved in carboxylesterase 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
Molecular weight:
67795.525
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. [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. [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. [10762042 ]
  4. Blesa R: Galantamine: therapeutic effects beyond cognition. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:28-34. [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. [11078030 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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. [12177686 ]
  8. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [12137632 ]
  9. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [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. [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. [12481195 ]
  12. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [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. [10592235 ]
General function:
Involved in carboxylesterase activity
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
Molecular weight:
68417.575
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. [17159811 ]
  2. Giacobini E: Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease? Drugs Aging. 2001;18(12):891-8. [11888344 ]
  3. Wilkinson DG: Galantamine: a new treatment for Alzheimer's disease. Expert Rev Neurother. 2001 Nov;1(2):153-9. [19811027 ]
General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in extracellular ligand-gated ion channel activity
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 ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular weight:
49704.3
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [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. [12177686 ]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [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. [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. [12481195 ]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [20480924 ]
General function:
Involved in extracellular ligand-gated ion channel activity
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 ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion
Gene Name:
CHRNA9
Uniprot ID:
Q9UGM1
Molecular weight:
54806.6
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [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. [12177686 ]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [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. [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. [12481195 ]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [20480924 ]
General function:
Involved in extracellular 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:
CHRNA2
Uniprot ID:
Q15822
Molecular weight:
59764.8
References
  1. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [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. [12177686 ]
  3. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [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. [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. [12481195 ]
  6. Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [20480924 ]