Identification
- Generic Name
- Methantheline
- DrugBank Accession Number
- DB00940
- Background
Methantheline is a synthetic antispasmodic. Antispasmodics are used to relieve cramps or spasms of the stomach, intestines, and bladder. Methantheline is used to treat intestine or stomach ulcers (peptic ulcer disease), intestine problems (irritable bowel syndrome), pancreatitis, gastritis, biliary dyskinesia, pylorosplasm, or urinary problems (reflex neurogenic bladder in children).
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Methantheline (DB00940)
- Weight
- Average: 340.436
Monoisotopic: 340.191268703 - Chemical Formula
- C21H26NO3
- Synonyms
- Methantheline
- Methantheline cation
- Methantheline ion
- Methanthelinium
- Methanthelinum
- External IDs
- MTB 51
Pharmacology
- Indication
For the treatment of peptic ulcer disease, irritable bowel syndrome, pancreatitis, gastritis, biliary dyskinesia, pylorosplasm, and reflex neurogenic bladder in children.
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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
Methantheline is a synthetic quarternary ammonium antimuscarinic used to relieve cramps or spasms of the stomach, intestines, and bladder. It can be used together with antacids or other medicines, such as H2-receptor antagonists, in the treatment of peptic ulcer. Methantheline inhibits muscarinic actions at postganglionic parasympathetic neuroeffector sites.
- Mechanism of action
Methantheline inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands. Depending on the dose, anticholinergics may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder.
Target Actions Organism AHistamine H2 receptor antagonistHumans UMuscarinic acetylcholine receptor M2 Not Available Humans UMuscarinic acetylcholine receptor M3 Not Available Humans UMuscarinic acetylcholine receptor M4 Not Available Humans UMuscarinic acetylcholine receptor M5 Not Available Humans UMuscarinic acetylcholine receptor M1 antagonistHumans - Absorption
Rapidly absorbed.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic, by enzymatic hydrolysis.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Symptoms of overdose: blurred vision (continuing) or changes in near vision, clumsiness or unsteadiness, confusion, convulsions, difficulty in breathing, muscle weakness (severe), or tiredness (severe), dizziness, drowsiness (severe), dryness of mouth, nose, or throat (severe), fast heartbeat, fever, hallucinations, slurred speech, unusual excitement, nervousness, restlessness, or irritability, unusual warmth, dryness, and flushing of skin.
- 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 softwareAclidinium The risk or severity of adverse effects can be increased when Methantheline is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Methantheline. Alfentanil The risk or severity of adverse effects can be increased when Methantheline is combined with Alfentanil. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Methantheline. Amantadine The risk or severity of adverse effects can be increased when Amantadine is combined with Methantheline. - 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 Methantheline bromide 090519SAPF 53-46-3 PQMWYJDJHJQZDE-UHFFFAOYSA-M - International/Other Brands
- Banthine / Vagantin
Categories
- ATC Codes
- A03AB07 — Methantheline
- Drug Categories
- Acid Reducers
- Agents producing tachycardia
- Alimentary Tract and Metabolism
- Amines
- Anticholinergic Agents
- Cholinergic Agents
- Drugs for Functional Gastrointestinal Disorders
- Gastric Acid Lowering Agents
- Histamine Antagonists
- Histamine H2 Antagonists
- Muscarinic Antagonists
- Neurotransmitter Agents
- Onium Compounds
- Quaternary Ammonium Compounds
- Synthetic Anticholinergics, Quaternary Ammonium Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrans
- Sub Class
- 1-benzopyrans
- Direct Parent
- Xanthenes
- Alternative Parents
- Diarylethers / Benzenoids / Tetraalkylammonium salts / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives show 3 more
- Substituents
- Amine / Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Diaryl ether / Ether / Hydrocarbon derivative / Monocarboxylic acid or derivatives show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- xanthenes (CHEBI:6817)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 36EI79TX7I
- CAS number
- 5818-17-7
- InChI Key
- GZHFODJQISUKAY-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H26NO3/c1-4-22(3,5-2)14-15-24-21(23)20-16-10-6-8-12-18(16)25-19-13-9-7-11-17(19)20/h6-13,20H,4-5,14-15H2,1-3H3/q+1
- IUPAC Name
- diethyl(methyl)[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium
- SMILES
- CC[N+](C)(CC)CCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C12
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015075
- KEGG Compound
- C07849
- PubChem Compound
- 4097
- PubChem Substance
- 46505807
- ChemSpider
- 3955
- 6821
- ChEBI
- 6817
- ChEMBL
- CHEMBL1201264
- ZINC
- ZINC000001530932
- Therapeutic Targets Database
- DAP001109
- PharmGKB
- PA164747037
- Wikipedia
- Methantheline
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 1 Completed Basic Science Neurogenic Bladder 1
Pharmacoeconomics
- Manufacturers
- Shire development inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000132 mg/mL ALOGPS logP 0.5 ALOGPS logP -0.47 Chemaxon logS -6.4 ALOGPS pKa (Strongest Acidic) 17.63 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 35.53 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 110.42 m3·mol-1 Chemaxon Polarizability 37.44 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9075 Blood Brain Barrier + 0.9411 Caco-2 permeable + 0.648 P-glycoprotein substrate Substrate 0.8327 P-glycoprotein inhibitor I Non-inhibitor 0.817 P-glycoprotein inhibitor II Non-inhibitor 0.5977 Renal organic cation transporter Non-inhibitor 0.5359 CYP450 2C9 substrate Non-substrate 0.8214 CYP450 2D6 substrate Non-substrate 0.599 CYP450 3A4 substrate Substrate 0.6801 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8476 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5637 Ames test Non AMES toxic 0.8371 Carcinogenicity Non-carcinogens 0.7407 Biodegradation Not ready biodegradable 0.5863 Rat acute toxicity 2.7675 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7426 hERG inhibition (predictor II) Inhibitor 0.7318
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0uk9-9611000000-3116f79dcd16074bb076 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]- 173.53685 predictedDeepCCS 1.0 (2019) [M+H]+ 175.89485 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.00243 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
- Gene Name
- HRH2
- Uniprot ID
- P25021
- Uniprot Name
- Histamine H2 receptor
- Molecular Weight
- 40097.65 Da
References
- Hough LB, Barker LA: Histamine H2-receptor antagonism by propantheline and derivatives. J Pharmacol Exp Ther. 1981 Nov;219(2):453-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Abrams P, Andersson KE: Muscarinic receptor antagonists for overactive bladder. BJU Int. 2007 Nov;100(5):987-1006. doi: 10.1111/j.1464-410X.2007.07205.x. [Article]
- Irmen M, Holze J, Bodefeld T, Trankle C: Characterization of methanthelinium binding and function at human M1-M5 muscarinic acetylcholine receptors. Naunyn Schmiedebergs Arch Pharmacol. 2018 Oct;391(10):1037-1052. doi: 10.1007/s00210-018-1525-1. Epub 2018 Jun 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- Abrams P, Andersson KE: Muscarinic receptor antagonists for overactive bladder. BJU Int. 2007 Nov;100(5):987-1006. doi: 10.1111/j.1464-410X.2007.07205.x. [Article]
- Irmen M, Holze J, Bodefeld T, Trankle C: Characterization of methanthelinium binding and function at human M1-M5 muscarinic acetylcholine receptors. Naunyn Schmiedebergs Arch Pharmacol. 2018 Oct;391(10):1037-1052. doi: 10.1007/s00210-018-1525-1. Epub 2018 Jun 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Guanyl-nucleotide exchange factor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM4
- Uniprot ID
- P08173
- Uniprot Name
- Muscarinic acetylcholine receptor M4
- Molecular Weight
- 53048.65 Da
References
- Irmen M, Holze J, Bodefeld T, Trankle C: Characterization of methanthelinium binding and function at human M1-M5 muscarinic acetylcholine receptors. Naunyn Schmiedebergs Arch Pharmacol. 2018 Oct;391(10):1037-1052. doi: 10.1007/s00210-018-1525-1. Epub 2018 Jun 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM5
- Uniprot ID
- P08912
- Uniprot Name
- Muscarinic acetylcholine receptor M5
- Molecular Weight
- 60073.205 Da
References
- Irmen M, Holze J, Bodefeld T, Trankle C: Characterization of methanthelinium binding and function at human M1-M5 muscarinic acetylcholine receptors. Naunyn Schmiedebergs Arch Pharmacol. 2018 Oct;391(10):1037-1052. doi: 10.1007/s00210-018-1525-1. Epub 2018 Jun 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Irmen M, Holze J, Bodefeld T, Trankle C: Characterization of methanthelinium binding and function at human M1-M5 muscarinic acetylcholine receptors. Naunyn Schmiedebergs Arch Pharmacol. 2018 Oct;391(10):1037-1052. doi: 10.1007/s00210-018-1525-1. Epub 2018 Jun 24. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Hallek M, Szinicz L: Methantheline improves the reactivation by HI 6 of human erythrocyte acetylcholinesterase inhibited by soman in vitro. Arch Toxicol. 1995;70(1):16-9. doi: 10.1007/s002040050243. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:46