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Identification
NameAnisotropine Methylbromide
Accession NumberDB00517  (APRD00800)
TypeSmall Molecule
GroupsApproved
Description

Anisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide 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. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.

Structure
Thumb
Synonyms
SynonymLanguageCode
8-Methyl-3-(2-propylpentanoyloxy)tropinium bromideNot AvailableNot Available
8-Methyltropinium bromide 2-propylpentanoateNot AvailableNot Available
8-Methyltropinium bromide 2-propylvalerateNot AvailableNot Available
Anisotropine methobromideNot AvailableNot Available
Anisotropine methylbromideNot AvailableNot Available
Endo-8,8-dimethyl-3-((1-oxo-2-propylpentyl)oxy)-8-azoniabicyclo(3.2.1)octane bromideNot AvailableNot Available
Methylbromure d'octatropineNot AvailableNot Available
Methyloctatropine bromideNot AvailableNot Available
Metilbromuro de octatropinaNot AvailableNot Available
Octatropine methylbromideNot AvailableINN
Octatropini methylbromidumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
EndovalpinNot Available
LytispasmNot Available
ValpinEndo
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number80-50-2
WeightAverage: 362.345
Monoisotopic: 361.16164192
Chemical FormulaC17H32BrNO2
InChI KeyQSFKGMJOKUZAJM-UHFFFAOYSA-M
InChI
InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1
IUPAC Name
8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azabicyclo[3.2.1]octan-8-ium bromide
SMILES
[Br-].CCCC(CCC)C(=O)O[C@H]1CC2CCC(C1)[N+]2(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Fatty acid ester
  • Fatty acyl
  • N-alkylpyrrolidine
  • Piperidine
  • Quaternary ammonium salt
  • Pyrrolidine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic bromide salt
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor use in conjunction with antacids or histamine H2-receptor antagonists in the treatment of peptic ulcer, to reduce further gastric acid secretion and delay gastric emptying.
PharmacodynamicsAnisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide 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. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.
Mechanism of actionQuaternary ammonium compounds such as anisotropine methylbromide inhibit 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.
AbsorptionGastrointestinal absorption is poor and irregular. Total absorption after an oral dose is about 10 to 25%.
Volume of distributionNot Available
Protein bindingNot Known
Metabolism

Hepatic, by enzymatic hydrolysis.

Route of eliminationNot Available
Half lifeNot Known
ClearanceNot Available
ToxicityNot Available
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-0.7332
Blood Brain Barrier+0.9683
Caco-2 permeable+0.602
P-glycoprotein substrateNon-substrate0.5078
P-glycoprotein inhibitor INon-inhibitor0.6258
P-glycoprotein inhibitor IINon-inhibitor0.8571
Renal organic cation transporterNon-inhibitor0.5586
CYP450 2C9 substrateNon-substrate0.8222
CYP450 2D6 substrateNon-substrate0.7474
CYP450 3A4 substrateSubstrate0.6949
CYP450 1A2 substrateNon-inhibitor0.7455
CYP450 2C9 substrateNon-inhibitor0.8657
CYP450 2D6 substrateNon-inhibitor0.7622
CYP450 2C19 substrateNon-inhibitor0.8572
CYP450 3A4 substrateNon-inhibitor0.937
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9752
Ames testNon AMES toxic0.7025
CarcinogenicityNon-carcinogens0.8765
BiodegradationReady biodegradable0.8093
Rat acute toxicity2.6936 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9113
hERG inhibition (predictor II)Non-inhibitor0.7206
Pharmacoeconomics
Manufacturers
  • Watson laboratories inc
  • Endo pharmaceuticals inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point329 °CWeiner, N. and Gordon, S.M.; US. Patent 2,962,499; November 29,1960; assigned to Endo Laboratories, Inc.
water solubility1600 mg/LNot Available
logP0.60Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.67e-05 mg/mLALOGPS
logP-0.4ALOGPS
logP-0.67ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.26 m3·mol-1ChemAxon
Polarizability34.09 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Weiner, N. and Gordon, S.M.; US. Patent 2,962,499; November 29,1960; assigned to Endo
Laboratories, Inc.

General ReferenceNot Available
External Links
ATC CodesNot Available
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
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

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
  3. Bachrach WH: Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug. Am J Dig Dis. 1972 Jun;17(6):505-12. Pubmed
  4. Tittor W, Lechmann R, Herrmann HJ, Dincer T, Weckesser G: [Effectiveness of octatropine methylbromide (OMB) in the treatment of gastritis, duodenal ulcer and spastic colon—a double blind study] ZFA (Stuttgart). 1982 Sep 30;58(27):1481-4. Pubmed
  5. Pace F, Maurano A, Ciacci C, Savarino V, Attili A, Iaquinto G, Magni E, Porro GB: Octatropine methyl bromide and diazepam combination (Valpinax) in patients with irritable bowel syndrome: a multicentre, randomized, placebo-controlled trial. Eur Rev Med Pharmacol Sci. 2010 Mar;14(3):155-62. Pubmed

2. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 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
  3. Bachrach WH: Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug. Am J Dig Dis. 1972 Jun;17(6):505-12. Pubmed

3. Muscarinic acetylcholine receptor M3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 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
  3. Bachrach WH: Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug. Am J Dig Dis. 1972 Jun;17(6):505-12. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on March 28, 2014 10:14