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Identification
NameMethantheline
Accession NumberDB00940  (APRD00751)
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
MethanthelineNot AvailableNot Available
MethantheliniumNot AvailableNot Available
MethanthelinumNot AvailableNot Available
SID11112123Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BanthineNot Available
VagantinNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Methantheline Bromide
Thumb
  • InChI Key: PQMWYJDJHJQZDE-UHFFFAOYSA-M
  • Monoisotopic Mass: 419.10960635
  • Average Mass: 420.34
DBSALT000228
Categories
CAS number5818-17-7
WeightAverage: 340.436
Monoisotopic: 340.191268703
Chemical FormulaC21H26NO3
InChI KeyGZHFODJQISUKAY-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthenes
Alternative Parents
Substituents
  • Xanthene
  • Diaryl ether
  • Acyl choline
  • Choline
  • Benzenoid
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of peptic ulcer disease, irritable bowel syndrome, pancreatitis, gastritis, biliary dyskinesia, pylorosplasm, and reflex neurogenic bladder in children.
PharmacodynamicsMethantheline 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 actionMethantheline 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.
AbsorptionRapidly absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic, by enzymatic hydrolysis.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9075
Blood Brain Barrier+0.9411
Caco-2 permeable+0.648
P-glycoprotein substrateSubstrate0.8327
P-glycoprotein inhibitor INon-inhibitor0.817
P-glycoprotein inhibitor IINon-inhibitor0.5977
Renal organic cation transporterNon-inhibitor0.5359
CYP450 2C9 substrateNon-substrate0.8214
CYP450 2D6 substrateNon-substrate0.599
CYP450 3A4 substrateSubstrate0.6801
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8931
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8476
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5637
Ames testNon AMES toxic0.8371
CarcinogenicityNon-carcinogens0.7407
BiodegradationNot ready biodegradable0.5863
Rat acute toxicity2.7675 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7426
hERG inhibition (predictor II)Inhibitor0.7318
Pharmacoeconomics
Manufacturers
  • Shire development inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000132 mg/mLALOGPS
logP0.5ALOGPS
logP-0.47ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)18.1ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity110.42 m3·mol-1ChemAxon
Polarizability37.44 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesA03AB07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H2 receptor P25021 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12