Hyoscine butylbromide

See also: Hyoscine hydrobromide

Hyoscine butylbromide

File:Butylscopolamine skeletal.svg
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
Clinical data
Trade names	Buscopan
Pregnancy category	AU: B2
Legal status	AU: S2 (Pharmacy only) UK: General sales list (GSL, OTC)
Routes of administration	Oral, rectal, intravenous
Pharmacokinetic data
Bioavailability	<1%
Protein binding	Low
Biological half-life	5 hours
Excretion	Renal (50%) and fecal
Identifiers
CAS Number	149-64-4 Y
ATC code	A03BB01 (WHO)
PubChem	CID: 160883
DrugBank	DB09300 Y
ChemSpider	16736107 Y
UNII	2Z3E1OF81V Y
ChEMBL	CHEMBL1256901 N
Chemical data
Formula	C21H30NO4+
Molecular mass	360.467 g/mol
SMILES [Br-].OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@@H]3[C@H]4O[C@H]4[C@H](C2)[N+]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 Y Key:HOZOZZFCZRXYEK-GSWUYBTGSA-M Y
NY (what is this?)  (verify)

Hyoscine butylbromide, also known as scopolamine butylbromide and sold under the brandname Buscopan, is a medication used to treat crampy abdominal pain, renal colic, and bladder spasms. It is also used to improve a death rattle 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, triggering of glaucoma, and severe allergies. Sleepiness however, is uncommon. It is unclear if it is safe in pregnancy. It is an anticholinergic agent, which does not have much effect on the brain.

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system. It is not available in the United States. The wholesale cost is 0.004 to 0.11 USD per pill as of 2014. It is manufactured from hyoscine which is naturally from the plant deadly nightshade.

Medical uses

Hyoscine butylbromide is effective in treating crampy abdominal pain.

Hyoscine butylbromide is effective in significantly reducing the duration of the first stage of labour, and it is not associated with any obvious adverse outcomes in mother or neonate.

Pharmacology

It is a quaternary ammonium compound and a semisynthetic derivative of scopolamine. The attachment of the butyl-bromide moiety effectively prevents the movement of this drug across the blood–brain barrier, effectively minimising undesirable central nervous system side effects associated with scopolamine/hyoscine.

Abuse

Hyoscine butylbromide is not centrally active and has a low incidence of abuse.

Names

Other names include butylscopolamine, scopolamine butylbromide, butylhyoscine, and butylscopolamine bromide.