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Ganstigmine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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Identification

Generic Name
Ganstigmine
DrugBank Accession Number
DB06525
Background

Ganstigmine is an orally active, geneserine derived, carbamate-based acetylcholinesterase inhibitor developed for the treatment of Alzheimer's disease.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 381.476
Monoisotopic: 381.205241741
Chemical Formula
C22H27N3O3
Synonyms
  • Ganstigmine
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Pharmacology

Indication

Investigated for use/treatment in alzheimer's disease.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AAcetylcholinesterase
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ganstigmine hydrochloride19OP2S99RQ412044-92-9CVDHRWXJJRBPFA-FKXUWVMKSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylcarbamic acid esters
Direct Parent
Phenylcarbamic acid esters
Alternative Parents
Indoles and derivatives / Dialkylarylamines / 1,2-oxazinanes / Carbamate esters / Oxacyclic compounds / N-organohydroxylamines / Azacyclic compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1,2-oxazinane / Amine / Aromatic heteropolycyclic compound / Azacycle / Carbamic acid ester / Carbonyl group / Dialkylarylamine / Hydrocarbon derivative / Indole or derivatives / N-organohydroxylamine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
QRR9SV89XI
CAS number
457075-21-7
InChI Key
ZOBDWFRKFSPCRB-UNMCSNQZSA-N
InChI
InChI=1S/C22H27N3O3/c1-5-15-8-6-7-9-18(15)23-21(26)27-16-10-11-19-17(14-16)22(2)12-13-24(3)28-20(22)25(19)4/h6-11,14,20H,5,12-13H2,1-4H3,(H,23,26)/t20-,22-/m0/s1
IUPAC Name
(4aS,9aS)-2,4a,9-trimethyl-2H,3H,4H,4aH,9H,9aH-[1,2]oxazino[6,5-b]indol-6-yl N-(2-ethylphenyl)carbamate
SMILES
CCC1=C(NC(=O)OC2=CC3=C(C=C2)N(C)[C@H]2ON(C)CC[C@@]32C)C=CC=C1

References

General References
Not Available
ChemSpider
7999041
BindingDB
10970
ChEMBL
CHEMBL121810
ZINC
ZINC000003814007

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
logP4.03ALOGPS
logP4.82Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.9Chemaxon
pKa (Strongest Basic)2.06Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.04 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity110.55 m3·mol-1Chemaxon
Polarizability42.45 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0019000000-11612f93e3d26ce647e4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-0389000000-95a72868c83c4e9873f1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-1594000000-b33fc3e6abf9af86d1c8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-9e31cb06b4b6b9febaed
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05cf-9853000000-4d9826e3e1945d2c06fd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lu-4091000000-f61a2fed45884af8ea2c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-207.4294035
predicted
DarkChem Lite v0.1.0
[M-H]-183.82655
predicted
DeepCCS 1.0 (2019)
[M+H]+208.9045035
predicted
DarkChem Lite v0.1.0
[M+H]+186.22209
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.7635035
predicted
DarkChem Lite v0.1.0
[M+Na]+192.2279
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Acetylcholinesterase
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Hydrolyzes rapidly the acetylcholine neurotransmitter released into the synaptic cleft allowing to terminate the signal transduction at the neuromuscular junction. Role in neuronal apoptosis
Specific Function
Acetylcholine binding
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Bartolucci C, Siotto M, Ghidini E, Amari G, Bolzoni PT, Racchi M, Villetti G, Delcanale M, Lamba D: Structural determinants of Torpedo californica acetylcholinesterase inhibition by the novel and orally active carbamate based anti-alzheimer drug ganstigmine (CHF-2819). J Med Chem. 2006 Aug 24;49(17):5051-8. [Article]
  2. Mazzucchelli M, Porrello E, Villetti G, Pietra C, Govoni S, Racchi M: Characterization of the effect of ganstigmine (CHF2819) on amyloid precursor protein metabolism in SH-SY5Y neuroblastoma cells. J Neural Transm (Vienna). 2003 Aug;110(8):935-47. [Article]
  3. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at March 19, 2008 16:35 / Updated at August 26, 2024 19:22