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Butylscopolamine
Systematic (IUPAC) name
[7(S)-(1α,2β,4β,5α,7β)]-9-butyl-7-(3-hydroxy-
1-oxo-2-phenylpropoxy)-9-methyl-3-oxa-
9-azonitricyclo[3.3.1.0(2,4)]nonane
Identifiers
CAS number 146-64-4
ATC code A03BB01
PubChem 160883
ChemSpider 16736107
Chemical data
Formula C21H30NO4+
Mol. mass 360.467 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability <1%
Protein binding Low
Half life 5 hours
Excretion Renal (50%) and fecal
Therapeutic considerations
Pregnancy cat. B2(AU)
Legal status Pharmacy Only (S2) (AU) GSL (UK)
Routes Oral, rectal, intravenous

Butylscopolamine, also known as scopolamine butylbromide and hyoscine butylbromide, is a peripherally acting antimuscarinic, anticholinergic agent[1] used as an abdominal-specific antispasmodic. It is a quaternary ammonium compound and a semisynthetic derivative of scopolamine. It is marketed under the trade name Buscopan by Boehringer Ingelheim GmbH, Germany, who also offer a combination of butylscopolamine and paracetamol, marketed under the name Buscopan Plus.

Butylscopolamine is used to treat pain and discomfort caused by abdominal cramps, menstrual cramps, or other spasmodic activity in the digestive system. It is not an analgesic in the normal sense, since it doesn't 'mask' or 'cover over' the pain, but rather works to prevent painful cramps and spasms from occurring in the first place. The attachment of the butyl-bromide moiety effectively prevents the movement of this drug across the blood-brain barrier, effectively minimising undesirable CNS side-effects associated with scopolamine/hyoscine.

Contents

Usage

Butylscopolamine is often prescribed at a low dosage, commonly 10 mg three times a day, as a means of managing some of the symptoms of irritable bowel syndrome. For horses it is used at 1.7 mg/100 pounds [nearest 100 pounds as possible]

Abuse

Butylscopolamine is generally not reported to be euphorogenic or strongly sedative, and has a low incidence of abuse. It should not be used for extended periods.

References

  1. ^ "Effects of β-Adrenergic Stimulation on the Acutely Obstructed Ureter in Dogs". Makoto Murakami, Yoshitaka Tomiyama, Kohichi Hayakawa, Masuo Akahane, Yukiyoshi Ajisawa, Young-Chol Park, Norio Ohnishi, Takahide Sugiyama and Takashi Kurita. Journal of Pharmacology and Experimental Therapeutics Vol. 292, Issue 1, pp. 67-75, January 2000.

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