Octatropine methylbromide

Octatropine methylbromide
Clinical data
Other names	8-Methyltropinium bromide 2- propylvalerate
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;
KEGG	D00232 ;
ChEMBL	ChEMBL1186610 ;
CompTox Dashboard (EPA)	DTXSID8022612 ;
ECHA InfoCard	100.001.169
Chemical and physical data
Formula	C17H32BrNO2
Molar mass	362.352 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Octatropine has been superseded by more effective agents in the treatment of peptic ulcer disease, and is no longer used.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

^ Triggle DJ, Ganellin CR, MacDonald F (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.
^ Batterman RC, Mouratoff GJ, Kaufman JE (May 1963). "Anisotropine methylbromide: a new antispasmodic for gastrointestinal disorders". Current Therapeutic Research, Clinical and Experimental. 5: 213–218. PMID 13966843.
^ Gyermek L (1998). "Semisynthetic Derivatives of Tropane Alkaloids and o Other Atropine Esters". 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". The American Journal of Digestive Diseases. 17 (6): 505–512. doi:10.1007/BF02231205. PMID 4555460. S2CID 7836183.

[DPA-1] Triggle DJ, Ganellin CR, MacDonald F (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". Current Therapeutic Research, Clinical and Experimental. 5: 213–218. PMID 13966843.

[3] Gyermek L (1998). "Semisynthetic Derivatives of Tropane Alkaloids and o Other Atropine Esters". 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". The American Journal of Digestive Diseases. 17 (6): 505–512. doi:10.1007/BF02231205. PMID 4555460. S2CID 7836183.

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