Distigmine

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

Identification

Summary

Distigmine is a cholinesterase inhibitor indicated in the treatment of neurogenic bladder dysfunction or myasthenia gravis.

Generic Name
Distigmine
DrugBank Accession Number
DB13694
Background

Distigmine is a parasympathomimetic agent with a longer duration of action and enhanced drug accumulation compared to Pyridostigmine and Neostigmine. It is an anticholinergic drug and long-acting reversible carbamate cholinesterase inhibitor that binds directly and competitively to the agonist binding sites of muscurinic receptors. Distigmine is available in several countries as a treatment of underactive detrusor and voiding dysfunction in the urinary tract where the active ingredient is distigmine bromide. It improves detrusor function thereby restoring normal voiding patterns in patients suffering from detrusor underactivity 2.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 416.521
Monoisotopic: 416.241258367
Chemical Formula
C22H32N4O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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.
DrugInteraction
AcebutololDistigmine may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Distigmine is combined with Acetylcholine.
AclidiniumDistigmine may increase the neuromuscular blocking activities of Aclidinium.
AmantadineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Distigmine.
AmifampridineThe risk or severity of adverse effects can be increased when Distigmine is combined with Amifampridine.
AmitriptylineThe therapeutic efficacy of Amitriptyline can be decreased when used in combination with Distigmine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Distigmine.
AmoxapineThe therapeutic efficacy of Amoxapine can be decreased when used in combination with Distigmine.
Anisotropine methylbromideThe therapeutic efficacy of Anisotropine methylbromide can be decreased when used in combination with Distigmine.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Distigmine.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Distigmine bromide750F36OP6J15876-67-2GJHSNEVFXQVOHR-UHFFFAOYSA-L

Categories

ATC Codes
N07AA03 — Distigmine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-methylpyridinium compounds. These are methylpyridines that carry a methyl group at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Methylpyridines
Direct Parent
N-methylpyridinium compounds
Alternative Parents
Pyridinium derivatives / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
show 1 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / N-methylpyridinium / Organic cation / Organic nitrogen compound
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinium ion (CHEBI:80756)
Affected organisms
Not Available

Chemical Identifiers

UNII
T940307O7B
CAS number
17299-00-2
InChI Key
AHZBEVXBKNYXPU-UHFFFAOYSA-N
InChI
InChI=1S/C22H32N4O4/c1-23-13-9-11-19(17-23)29-21(27)25(3)15-7-5-6-8-16-26(4)22(28)30-20-12-10-14-24(2)18-20/h9-14,17-18H,5-8,15-16H2,1-4H3/q+2
IUPAC Name
1-methyl-3-{[methyl({6-[methyl({[(1-methylpyridin-1-ium-3-yl)oxy]carbonyl})amino]hexyl})carbamoyl]oxy}pyridin-1-ium
SMILES
CN(CCCCCCN(C)C(=O)OC1=C[N+](C)=CC=C1)C(=O)OC1=C[N+](C)=CC=C1

References

General References
  1. Harada T, Fushimi K, Kato A, Ito Y, Nishijima S, Sugaya K, Yamada S: Demonstration of muscarinic and nicotinic receptor binding activities of distigmine to treat detrusor underactivity. Biol Pharm Bull. 2010;33(4):653-8. [Article]
  2. Bougas DA, Mitsogiannis IC, Mitropoulos DN, Kollaitis GC, Serafetinides EN, Giannopoulos AM: Clinical efficacy of distigmine bromide in the treatment of patients with underactive detrusor. Int Urol Nephrol. 2004;36(4):507-12. [Article]
KEGG Compound
C16823
PubChem Compound
3116
PubChem Substance
347829310
ChemSpider
3004
RxNav
3551
ChEBI
80756
ChEMBL
CHEMBL1199307
ZINC
ZINC000003872328
Wikipedia
Distigmine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular
TabletOral5 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000462 mg/mLALOGPS
logP-2.7ALOGPS
logP-5.6ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)19.23ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.84 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity116.06 m3·mol-1ChemAxon
Polarizability47.47 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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

Drug created on June 23, 2017 20:46 / Updated on May 29, 2021 18:12