Octatropine methylbromide

Octatropine methylbromide
Clinical data
Other names8-Methyltropinium bromide 2- propylvalerate
Routes of
administration		Oral
ATC code
  • none
Pharmacokinetic data
Bioavailability10 to 25% (oral)
Protein bindingUnknown
MetabolismHepatic
Elimination half-lifeUnknown
Identifiers
IUPAC name
  • (endo)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate bromide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.169
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Chemical and physical data
FormulaC17H32BrNO2
Molar mass362.352 g·mol−1
3D model (JSmol)
SMILES
  • CCCC(CCC)C(=O)O[C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C.[Br-]
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/t14-,15+,16+; ☒N
  • Key:QSFKGMJOKUZAJM-CNKDKAJDSA-M ☒N
 ☒NcheckY (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Octatropine has been superseded by more effective agents in the treatment of peptic ulcer disease, and is no longer used.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.

References

  1. ↑ David J. Triggle; C. R. Ganellin; F. MacDonald (1997). Dictionary of Pharmacological Agents. Vol. 2. Boca Raton: Chapman & Hall/CRC. p. 1467. ISBN 0-412-46630-9. Retrieved on August 31, 2008 through Google Book Search.
  2. ↑ Batterman RC, Mouratoff GJ, Kaufman JE (May 1963). "Anisotropine methylbromide: a new antispasmodic for gastrointestinal disorders". Curr Ther Res Clin Exp. 5: 213–8. PMID 13966843.
  3. ↑ Gyermek, Laszlo (1998). Pharmacology of antimuscarinic agents. Boca Raton: CRC Press. p. 183. ISBN 0-8493-8559-8. Retrieved on August 31, 2008 through Google Book Search.
  4. ↑ Bachrach WH (June 1972). "Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug". Am J Dig Dis. 17 (6): 505–12. doi:10.1007/BF02231205. PMID 4555460. S2CID 7836183.


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