Distigmine

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

Identification

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Name
Distigmine
Accession Number
DB13694
Type
Small Molecule
Groups
Experimental
Description

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.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
T940307O7B
CAS number
17299-00-2
Weight
Average: 416.521
Monoisotopic: 416.241258367
Chemical Formula
C22H32N4O4
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Distigmine.
AgmatineThe therapeutic efficacy of Agmatine can be decreased when used in combination with Distigmine.
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with Distigmine.
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.
AprobarbitalThe therapeutic efficacy of Aprobarbital can be decreased when used in combination with Distigmine.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Distigmine.
AtracuriumThe therapeutic efficacy of Atracurium can be decreased when used in combination with Distigmine.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Evidence Level

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Food Interactions
Not Available

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. [PubMed:20410601]
  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. [PubMed:15787326]
External Links
KEGG Compound
C16823
PubChem Compound
3116
PubChem Substance
347829310
ChemSpider
3004
ChEBI
80756
ChEMBL
CHEMBL1199307
Wikipedia
Distigmine
ATC Codes
N07AA03 — Distigmine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
N-methylpyridinium / Pyridinium / Carbamic acid ester / Heteroaromatic compound / Carbonic acid derivative / Azacycle / Organic oxide / Organopnictogen compound / Organic oxygen compound / Organooxygen compound
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinium ion (CHEBI:80756)

Drug created on June 23, 2017 14:46 / Updated on May 01, 2019 11:50