Anisotropine Methylbromide

Title: Anisotropine Methylbromide
CAS Registry Number: 80-50-2
CAS Name: endo-8,8-Dimethyl-3-[(1-oxo-2-propylpentyl)oxy]-8-azoniabicyclo[3.2.1]octane bromide
Additional Names: 3a-hydroxy-8-methyl-1aH,5aH-tropanium bromide 2-propylvalerate; 8-methyltropinium bromide 2-propylvalerate; 8-methyl-3-(2-propylpentanoyloxy)tropinium bromide; octatropine methylbromide
Trademarks: Valpin (Endo)
Molecular Formula: C17H32BrNO2
Molecular Weight: 362.35
Percent Composition: C 56.35%, H 8.90%, Br 22.05%, N 3.87%, O 8.83%
Literature References: Anticholinergic. Prepn: Weiner, Gordon, US 2962499 (1960 to Endo Labs.). Metabolism: Shindo et al., Chem. Pharm. Bull. 19, 513 (1971). Clinical trial in ulcer: J. H. Bowers et al., J. Clin. Pharmacol. 18, 365 (1978).
Properties: Crystals from acetone, mp 329°.
Melting point: mp 329°
Derivative Type: Methyl chloride
Molecular Formula: C17H32ClNO2
Molecular Weight: 317.89
Percent Composition: C 64.23%, H 10.15%, Cl 11.15%, N 4.41%, O 10.07%
Properties: Crystals from acetone, mp 289°.
Melting point: mp 289°
Therap-Cat: Antispasmodic.
Keywords: Antimuscarinic; Antispasmodic.
Anistreplase Annatto Annexins Annotinine Anot

Octatropine methylbromide
Octatropine methylbromide.svg
Systematic (IUPAC) name
(endo)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate bromide
Clinical data
Pregnancy cat. C (US)
Legal status  ?
Routes Oral
Pharmacokinetic data
Bioavailability 10 to 25% (oral)
Protein binding Unknown
Metabolism Hepatic
Half-life Unknown
Identifiers
CAS number 80-50-2 YesY
ATC code None
PubChem CID 6647
DrugBank DB00517
UNII 62M960DHIL N
ChEMBL CHEMBL1186610 N
Synonyms 8-Methyltropinium bromide 2- propylvalerate
Chemical data
Formula C17H32BrNO2 
Mol. mass 362.345 g/mol
 N (what is this?)  (verify)

Octatropine methylbromide (INN) or anisotropine methylbromide (USAN), trade names Valpin, Endovalpin, Lytispasm and others,[1] is a muscarinic antagonist and antispasmodic. It was introduced to the U.S. market in 1963 as an adjunct in the treatment of peptic ulcer,[2] and promoted as being more specific to the gastrointestinal tract than other anticholinergics, although its selectivity was questioned in later studies.[3][4]

Octatropine has been superseded by more effective agents in the treatment of peptic ulcer disease, and is no longer used. It is still sold in some countries in combination with other drugs, such as phenobarbital and metamizole.