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Identification
Name Methantheline
Accession Number DB00940 (APRD00751)
Type small molecule
Groups approved
Description

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).
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
Banthine Bromide
Methantheline Bromide
Methanthelinium
Methanthelinium Bromide
Methanthelinum
Methanthine Bromide
MTB 51
Salts Not Available
Brand names
Name Company
Asabaine
Avagal
Banthin
Banthine
Dixamone Bromide
Doladene
Frenogastrico
Gastrin I
Gastrin-1 Human
Gastron
Gastrosedan
Mantheline
Metantyl
Metaxan
Methanide
Methelina
Resobantin
Ulcine
Ulcudexter
Vagamin
Vagantin
Xanteline
First Prev Next Last
Brand mixtures Not Available
Categories
  • Antispasmodics
  • Anticholinergic Agents
CAS number 5818-17-7
Weight Average: 340.436
Monoisotopic: 340.191268703
Chemical Formula C21H26NO3
InChI Key InChIKey=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
Plain Text
IUPAC Name
diethyl(methyl){2-[(9H-xanthen-9-yl)carbonyloxy]ethyl}azanium
SMILES
CC[N+](C)(CC)CCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C12
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Xanthenes
Substructures
  • Xanthenes
  • Carboxylic Acids and Derivatives
  • Pyrans
  • Acetates
  • Phenols and Derivatives
  • Phenylacetates
  • Ethers
  • Benzene and Derivatives
  • Quaternary Ammonium Salts
  • Benzopyrans
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Phenyl Esters
  • Cations
Pharmacology
Indication For the treatment of peptic ulcer disease, irritable bowel syndrome, pancreatitis, gastritis, biliary dyskinesia, pylorosplasm, and reflex neurogenic bladder in children.
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.
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
Toxicity 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.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Shire development inc
Packagers Not Available
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 1.32e-04 g/l ALOGPS
logP 0.5 ALOGPS
logP -0.47 ChemAxon
logS -6.5 ALOGPS
pKa (strongest acidic) 18.1 ChemAxon
pKa (strongest basic) -7.2 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 35.53 ChemAxon
rotatable bond count 7 ChemAxon
refractivity 110.42 ChemAxon
polarizability 37.44 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07849 Link_out
PubChem Compound 4097 Link_out
PubChem Substance 46505807 Link_out
ChemSpider 3955 Link_out
Therapeutic Targets Database DAP001109 Link_out
PharmGKB PA164747037 Link_out
ATC Codes
  • A03AB07
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Haloperidol The anticholinergic increases the risk of psychosis and tardive dyskinesia
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Methantheline, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Trimethobenzamide Trimethobenzamide and Methantheline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Methantheline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium Trospium and Methantheline, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Histamine H2 receptor

Pharmacological action: yes
Actions: antagonist

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 differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway

Organism class: human
UniProt ID: P25021 Link_out
Gene: HRH2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hough LB, Barker LA: Histamine H2-receptor antagonism by propantheline and derivatives. J Pharmacol Exp Ther. 1981 Nov;219(2):453-8. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19