Misplaced Pages

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 21:20, 29 August 2011 (Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WikiProject_Pharm). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Hyoscine butylbromide

Clinical data
Pregnancy category	AU: B2
Routes of administration	Oral, rectal, intravenous
ATC code	A03BB01 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy medicine) UK: General sales list (GSL, OTC)
Pharmacokinetic data
Bioavailability	<1%
Protein binding	Low
Elimination half-life	5 hours
Excretion	Renal (50%) and fecal
Identifiers
IUPAC name -9-butyl-7-(3-hydroxy- 1-oxo-2-phenylpropoxy)-9-methyl-3-oxa- 9-azonitricyclononane
CAS Number	149-64-4
PubChem CID	160883
ChemSpider	16736107
UNII	2Z3E1OF81V
CompTox Dashboard (EPA)	DTXSID1022718
ECHA InfoCard	100.005.223
Chemical and physical data
Formula	C21H30NO4
Molar mass	360.467 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES .OC(c1ccccc1)C(=O)O2C34O4(C2)3(C)CCCC
InChI InChI=1S/C21H30NO4.BrH/c1-3-4-10-22(2)17-11-15(12-18(22)20-19(17)26-20)25-21(24)16(13-23)14-8-6-5-7-9-14;/h5-9,15-20,23H,3-4,10-13H2,1-2H3;1H/q+1;/p-1/t15-,16-,17-,18+,19-,20+,22?;/m1./s1 Key:HOZOZZFCZRXYEK-GSWUYBTGSA-M
(verify)

Butylscopolamine, also known as scopolamine butylbromide, butylhyoscine and hyoscine butylbromide, is a peripherally acting antimuscarinic, anticholinergic agent 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.

Usage

Butylscopolamine is to treat cramping abdominal pain with some success.

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.
2. 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.

External links

• Buscopan/Buscapina from Boehringer Ingelheim
• IBS relief from Boehringer Ingelheim

• Anticholinergics
• Propionates
• Quaternary ammonium compounds