Ganstigmine

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

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
Thumb
Weight
Average: 381.476
Monoisotopic: 381.205241741
Chemical Formula
C22H27N3O3
Synonyms
  • Ganstigmine

Pharmacology

Indication

Investigated for use/treatment in alzheimer's disease.

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot AvailableHumans
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
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine hydrolase 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
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]

Drug created on March 19, 2008 16:35 / Updated on February 21, 2021 18:52