galantamine   Click here for help

GtoPdb Ligand ID: 6693

Synonyms: galanthamine | Razadyne®
Approved drug PDB Ligand
galantamine is an approved drug (FDA (2001))
Compound class: Synthetic organic
Comment: Many alternative stereo forms exist for the structure. The marketed formulation contains galantamine hydrobromide (PubChem CID 121587).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: galantamine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 41.93
Molecular weight 287.15
XLogP 1.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COc1ccc2c3c1OC1C3(CCN(C2)C)C=CC(C1)O
Isomeric SMILES COc1ccc2c3c1O[C@@H]1[C@@]3(CCN(C2)C)C=C[C@@H](C1)O
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
InChI Key ASUTZQLVASHGKV-JDFRZJQESA-N
References
1. Ago Y, Koda K, Takuma K, Matsuda T. (2011)
Pharmacological aspects of the acetylcholinesterase inhibitor galantamine.
J Pharmacol Sci, 116 (1): 6-17. [PMID:21498956]
2. Clark JK, Cowley P, Muir AW, Palin R, Pow E, Prosser AB, Taylor R, Zhang MQ. (2002)
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
Bioorg Med Chem Lett, 12 (18): 2565-8. [PMID:12182861]
3. Prvulovic D, Hampel H, Pantel J. (2010)
Galantamine for Alzheimer's disease.
Expert Opin Drug Metab Toxicol, 6 (3): 345-54. [PMID:20113148]
4. Taly A, Corringer PJ, Guedin D, Lestage P, Changeux JP. (2009)
Nicotinic receptors: allosteric transitions and therapeutic targets in the nervous system.
Nat Rev Drug Discov, 8 (9): 733-50. [PMID:19721446]