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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
Salts
Name/CAS Structure Properties
Methantheline Bromide
Thumb
  • InChI Key: PQMWYJDJHJQZDE-UHFFFAOYSA-M
  • Monoisotopic Mass: 419.10960635
  • Average Mass: 420.34
DBSALT000228
Brand names
NameCompany
BanthineNot Available
VagantinNot Available
Brand mixturesNot Available
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-xanthen-9-yl)carbonyloxy]ethyl}azanium
SMILES
CC[N+](C)(CC)CCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C12
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzopyrans
SubclassDibenzopyrans
Direct parentXanthenes
Alternative parentsDiarylethers; Cholines; Benzene and Substituted Derivatives; Carboxylic Acid Esters; Enolates; Polyamines
Substituentsdiaryl ether; choline; benzene; carboxylic acid ester; carboxylic acid derivative; polyamine; ether; enolate; amine; organonitrogen compound
Classification descriptionThis compound belongs to the xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene ring joined to each other by a pyran ring.
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
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8931
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Shire development inc
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.32e-04 g/lALOGPS
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 area35.53ChemAxon
rotatable bond count7ChemAxon
refractivity110.42ChemAxon
polarizability37.44ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07849
PubChem Compound4097
PubChem Substance46505807
ChemSpider3955
Therapeutic Targets DatabaseDAP001109
PharmGKBPA164747037
ATC CodesA03AB07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
HaloperidolThe anticholinergic increases the risk of psychosis and tardive dyskinesia
TacrineThe 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.
TrimethobenzamideTrimethobenzamide and Methantheline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Methantheline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium and Methantheline, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
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