Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:39:03 UTC
HMDB IDHMDB0014812
Secondary Accession Numbers
  • HMDB14812
Metabolite Identification
Common NameGalantamine
DescriptionGalantamine, also known as reminyl or nivalin, 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. Galantamine is a drug which is used 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. Galantamine is a very strong basic compound (based on its pKa). Galantamine is a potentially toxic compound. A benzazepine alkaloid isolated from certain species of daffodils.
Structure
Data?1582753223
Synonyms
ValueSource
(-)-GALANTHAMINEChEBI
ReminylKegg
GalanthamineHMDB
Galanthamine hydrobromideHMDB
LycoremineHMDB
GalantaminHMDB
RazadyneHMDB
NivalinHMDB
NivalineHMDB
Ortho mcneil neurologics brand OF galantamineHMDB
Ortho-mcneil neurologics brand OF galantamineHMDB
GalantamineChEBI
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 KeyASUTZQLVASHGKV-JDFRZJQESA-N
Chemical Taxonomy
Description 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
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Azepine
  • Aralkylamine
  • Benzenoid
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point269 - 270 °C (hydrogen bromide salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility1.7 g/LNot Available
LogP1.8Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM166.930932474
AllCCS[M+H]+Not Available166.68http://allccs.zhulab.cn/database/detail?ID=AllCCS00001355
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.7 g/LALOGPS
logP10(1.39) g/LALOGPS
logP10(1.16) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)14.81ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.3 m³·mol⁻¹ChemAxon
Polarizability31.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.32731661259
DarkChem[M-H]-165.731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Galantamine,1TMS,#1COC1=CC=C2CN(C)CC[C@@]34C=C[C@H](O[Si](C)(C)C)C[C@@H]3OC1=C242367.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galantamine,1TBDMS,#1COC1=CC=C2CN(C)CC[C@@]34C=C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]3OC1=C242608.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Galantamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-010u-2090000000-ce0fee33e6fee456fb642017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galantamine GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-9137000000-e759a1bc34f4897650112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galantamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000l-5980000000-928ad889466b6a2b38272014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Galantamine , positive-QTOFsplash10-000i-0390000000-f4f443a7f842d92dec392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Galantamine 35V, Positive-QTOFsplash10-03ei-0390000000-5f20c8cd1421554a23652021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 10V, Positive-QTOFsplash10-00dr-0090000000-c09fea1137eb040ccff32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 20V, Positive-QTOFsplash10-00dr-1090000000-e8fc73122c750f4a8b292016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 40V, Positive-QTOFsplash10-1000-4190000000-4e6f34da3d49bbf029b42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 10V, Negative-QTOFsplash10-000i-0090000000-d57ff615302227895e9b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 20V, Negative-QTOFsplash10-000i-0090000000-084d311da94f251627eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 40V, Negative-QTOFsplash10-0w2c-1490000000-3ee999f09979ab3820f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 10V, Positive-QTOFsplash10-000i-0090000000-8e23f9bfe8905382513a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 20V, Positive-QTOFsplash10-0079-0090000000-a9adf4464f8392bb18ad2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 40V, Positive-QTOFsplash10-000l-1090000000-cd82eceaf8d38fd372982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 10V, Negative-QTOFsplash10-000i-0090000000-32affc6af32f5da1d2572021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 20V, Negative-QTOFsplash10-000i-0090000000-6b6acbca4d5713d4973f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galantamine 40V, Negative-QTOFsplash10-02u3-0090000000-5c86743e445ac6cabb6a2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00674 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00674 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00674
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001570
Chemspider ID9272
KEGG Compound IDC08526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGalantamine
METLIN IDNot Available
PubChem Compound9651
PDB IDNot Available
ChEBI ID42944
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed:10606746 ]
  2. Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632 ]
  3. Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124 ]
  4. Birks J: Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst Rev. 2006 Jan 25;(1):CD005593. [PubMed: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. [PubMed: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. [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: [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 ]
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. [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 ]
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. [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: [PubMed: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. [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: [PubMed: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. [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: [PubMed:20480924 ]