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targets (3)
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Identification
Name Anisotropine Methylbromide
Accession Number DB00517 (APRD00800)
Type small molecule
Groups approved
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 Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents.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
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Anisotropine methobromide
Endovalpin
Lytispasm
Methyloctatropine bromide
Octatropine
Valpin 50
Brand mixtures Not Available
Categories
  • Anticholinergics
  • Parasympatholytics
CAS number 80-50-2
Weight Average: 362.345
Monoisotopic: 361.16164192
Chemical Formula C17H32BrNO2
InChI Key InChIKey=QSFKGMJOKUZAJM-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
Plain Text
IUPAC Name
(3S)-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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For 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.
Pharmacodynamics 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 Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents.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.
Mechanism of action Quaternary 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.
Absorption Gastrointestinal absorption is poor and irregular. Total absorption after an oral dose is about 10 to 25%.
Volume of distribution Not Available
Protein binding Not Known
Metabolism Hepatic, by enzymatic hydrolysis.
Route of elimination Not Available
Half life Not Known
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Watson laboratories inc
  • Endo pharmaceuticals inc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 329 °C PhysProp
water solubility 1600 mg/L Not Available
logP 0.60 Not Available
Predicted Properties
Property Value Source
water solubility 9.67e-05 g/l ALOGPS
logP -0.4 ALOGPS
logP -0.67 ChemAxon
logS -6.6 ALOGPS
pKa (strongest basic) -7.1 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 26.3 ChemAxon
rotatable bond count 7 ChemAxon
refractivity 93.26 ChemAxon
polarizability 34.09 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00232 Link_out
KEGG Compound C06830 Link_out
ChEBI 2739 Link_out
ChEMBL 2739 Link_out
Therapeutic Targets Database DAP000837 Link_out
PharmGKB PA164754880 Link_out
ATC Codes Not Available
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
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
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
  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

Pharmacological action: yes
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 adenylate cyclase inhibition

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 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
  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

Pharmacological action: yes
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: P20309 Link_out
Gene: CHRM3 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
  3. Bachrach WH: Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug. Am J Dig Dis. 1972 Jun;17(6):505-12. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19