Octatropine methylbromide

Octatropine methylbromide
Clinical data
Other names	8-Methyltropinium bromide 2- propylvalerate
Pregnancy; category	US: C (Risk not ruled out) ;
Routes of; administration	Oral
ATC code	none;
Pharmacokinetic data
Bioavailability	10 to 25% (oral)
Protein binding	Unknown
Metabolism	Hepatic
Elimination half-life	Unknown
Identifiers
	IUPAC name (endo)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate bromide;
CAS Number	80-50-2 ;
PubChem CID	6647;
DrugBank	DB00517 ;
ChemSpider	10482228 ;
UNII	62M960DHIL;
ChEMBL	ChEMBL1186610 ;
CompTox Dashboard (EPA)	DTXSID8022612 ;
ECHA InfoCard	100.001.169
Chemical and physical data
Formula	C17H32BrNO2
Molar mass	362.345 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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+; ; Key:QSFKGMJOKUZAJM-CNKDKAJDSA-M ;
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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Octatropine has been superseded by more effective agents in the treatment of peptic ulcer disease, and is no longer used.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

David J. Triggle; C. R. Ganellin; F. MacDonald (1997). Dictionary of Pharmacological Agents. 2. Boca Raton: Chapman & Hall/CRC. p. 1467. ISBN 0-412-46630-9. Retrieved on August 31, 2008 through Google Book Search.
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.
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.
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.

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[DPA-1] David J. Triggle; C. R. Ganellin; F. MacDonald (1997). Dictionary of Pharmacological Agents. 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.