benzgalantamine   Click here for help

GtoPdb Ligand ID: 13477

Synonyms: alpha-1062 | galantamine benzoate | Gln-1062 | memogain | Zunveyl®
Approved drug
benzgalantamine is an approved drug (FDA (2024))
Compound class: Synthetic organic
Comment: Benzgalantamine is an orally bioavailable prodrug of the active acetylcholinesterase inhibitor galantamine [2-3].

benzgalantamine is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 5
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 48
Molecular weight 391.46
XLogP 2.73
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C3C(=CC=C4OC)C1)OC(=O)C5=CC=CC=C5
Isomeric SMILES CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)OC(=O)C5=CC=CC=C5
InChI InChI=1S/C24H25NO4/c1-25-13-12-24-11-10-18(28-23(26)16-6-4-3-5-7-16)14-20(24)29-22-19(27-2)9-8-17(15-25)21(22)24/h3-11,18,20H,12-15H2,1-2H3/t18-,20-,24-/m0/s1
InChI Key JKVNJTYHRABHIY-WXVUKLJWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Baakman AC, 't Hart E, Kay DG, Stevens J, Klaassen ES, Maelicke A, Groeneveld GJ. (2016)
First in human study with a prodrug of galantamine: Improved benefit-risk ratio?.
Alzheimers Dement (N Y), 2 (1): 13-22. [PMID:29067291]
2. Bakker C, van der Aart J, Hart EP, Klaassen ES, Bergmann KR, van Esdonk MJ, Kay DG, Groeneveld GJ. (2020)
Safety, pharmacokinetics, and pharmacodynamics of Gln-1062, a prodrug of galantamine.
Alzheimers Dement (N Y), 6 (1): e12093. [PMID:33083515]
3. Maelicke A, Hoeffle-Maas A, Ludwig J, Maus A, Samochocki M, Jordis U, Koepke AK. (2010)
Memogain is a galantamine pro-drug having dramatically reduced adverse effects and enhanced efficacy.
J Mol Neurosci, 40 (1-2): 135-7. [PMID:19669943]