Hyoscine butylbromide

Hyoscine butylbromide
Clinical data
Trade names	Buscopan, others
Other names	scopolamine butylbromide, butylscopolamine bromide (JAN JP)
License data	US DailyMed: n-butylscopolammonium_bromide;
Routes of; administration	By mouth, rectal, intravenous
ATC code	A03BB01 (WHO) A03DB04 (WHO), QA03BB01 (WHO);
Legal status
Legal status	AU: S2 (Pharmacy medicine); CA: OTC (Pharmacist only); UK: General sales list (GSL, OTC); US: ℞-only; In general: Over-the-counter (OTC);
Pharmacokinetic data
Bioavailability	<1%
Protein binding	Low
Elimination half-life	5 hours
Excretion	Kidney (50%) and fecal
Identifiers
	IUPAC name [7(S)-(1α,2β,4β,5α,7β)]-9-butyl-7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9-methyl-3-oxa-; 9-azonitricyclo[3.3.1.02,4]nonane;
CAS Number	149-64-4 ;
PubChem CID	6852391;
DrugBank	DBSALT002585 ;
ChemSpider	16736107 ;
UNII	0GH9JX37C8;
KEGG	D01451;
ChEBI	CHEBI:32123;
ChEMBL	ChEMBL1256901 ;
CompTox Dashboard (EPA)	DTXSID1022718 ;
ECHA InfoCard	100.005.223
Chemical and physical data
Formula	C21H30BrNO4+
Molar mass	440.378 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC[N+]1(C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4)C.[Br-];
	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-HNHWXVNLSA-M ;
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Hyoscine butylbromide, also known as scopolamine butylbromide and sold under the brand name Buscopan among others, is an anticholinergic medication used to treat abdominal pain, esophageal spasms, bladder spasms, biliary colic, and renal colic. It is also used to improve excessive respiratory secretions at the end of life. Hyoscine butylbromide can be taken by mouth, injection into a muscle, or into a vein.

Side effects may include sleepiness, vision changes, dry mouth, rapid heart rate, triggering of glaucoma, and severe allergies. Sleepiness is uncommon. It is unclear if it is safe in pregnancy. It appears safe in breastfeeding. Greater care is recommended in those with heart problems. It is an anticholinergic agent, which does not have much effect on the brain.

Hyoscine butylbromide was patented in 1950, and approved for medical use in 1951. It is on the World Health Organization's List of Essential Medicines. In the United States, it is available only for the medical treatment of horses, and the similar compound methscopolamine is used in humans instead. It is manufactured from hyoscine – also known as scopolamine – which occurs naturally in a variety of plants in the nightshade family, Solanaceae, including deadly nightshade (Atropa belladonna).