Butylscopolamine
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| 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 |
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| Clinical data | |
| Pregnancy cat. | B2 (AU) |
| Legal status | Pharmacy Only (S2) (AU) GSL (UK) |
| Routes | Oral, rectal, intravenous |
| Pharmacokinetic data | |
| Bioavailability | <1% |
| Protein binding | Low |
| Half-life | 5 hours |
| Excretion | Renal (50%) and fecal |
| Identifiers | |
| CAS number | 149-64-4 |
| ATC code | A03BB01 |
| PubChem | CID 160883 |
| ChemSpider | 16736107  |
| UNII | 2Z3E1OF81V |
| Chemical data | |
| Formula | C21H30NO4+ |
| Mol. mass | 360.467 g/mol |
| SMILES | eMolecules & PubChem |
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Butylscopolamine, also known as scopolamine butylbromide, butylhyoscine 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 (in some countries, Buscopan Compositum).
Butylscopolamine is used to treat pain and discomfort caused by abdominal cramps, menstrual cramps, or other spasmodic activity in the digestive system. It is also effective at preventing bladder spasms. 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.
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[edit] Medical uses
Butylscopolamine is used to treat cramping abdominal pain with some success.[2]
[edit] 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.
[edit] References
- ^ "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.
- ^ Tytgat GN (2007). "Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain". Drugs 67 (9): 1343–57. PMID 17547475.
[edit] External links
- Buscopan/Buscapina from Boehringer Ingelheim
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