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
Structure for Distigmine (DB13694)
- Weight
- Average: 416.521
Monoisotopic: 416.241258367 - Chemical Formula
- C22H32N4O4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Myasthenia gravis •••••••••••• •••••• Treatment of Neurogenic voiding disorders •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Distigmine may increase the bradycardic activities of Acebutolol. Acetylcholine The risk or severity of adverse effects can be increased when Distigmine is combined with Acetylcholine. Aclidinium Distigmine may increase the neuromuscular blocking activities of Aclidinium. Amantadine The therapeutic efficacy of Amantadine can be decreased when used in combination with Distigmine. Amifampridine The risk or severity of adverse effects can be increased when Distigmine is combined with Amifampridine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Distigmine bromide 750F36OP6J 15876-67-2 GJHSNEVFXQVOHR-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
- 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]
- 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]
- External Links
- KEGG Compound
- C16823
- PubChem Compound
- 3116
- PubChem Substance
- 347829310
- ChemSpider
- 3004
- 3551
- ChEBI
- 80756
- ChEMBL
- CHEMBL1199307
- ZINC
- ZINC000003872328
- Wikipedia
- Distigmine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intramuscular Tablet Oral 5 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000462 mg/mL ALOGPS logP -2.7 ALOGPS logP -5.6 Chemaxon logS -6 ALOGPS pKa (Strongest Acidic) 19.23 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 66.84 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 116.06 m3·mol-1 Chemaxon Polarizability 47.47 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 213.1322402 predictedDarkChem Lite v0.1.0 [M-H]- 187.1752 predictedDeepCCS 1.0 (2019) [M+H]+ 212.9168402 predictedDarkChem Lite v0.1.0 [M+H]+ 189.7831 predictedDeepCCS 1.0 (2019) [M+Na]+ 213.5568402 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.42119 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:46 / Updated at May 29, 2021 18:12