Butylscopolamine

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Butylscopolamine
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
Pregnancy cat.
Legal status
Routes Oral, rectal, intravenous
Pharmacokinetic data
Bioavailability <1%
Protein binding Low
Half-life 5 hours
Excretion Renal (50%)[citation needed] and fecal
Identifiers
CAS number 149-64-4 YesY
ATC code A03BB01
PubChem CID 160883
ChemSpider 16736107 YesY
UNII 2Z3E1OF81V YesY
ChEMBL CHEMBL1256901 N
Chemical data
Formula C21H30NO4+
Mol. mass 360.467 g/mol
 N (what is this?)  (verify)

Butylscopolamine — also known as scopolamine butylbromide, butylhyoscine, butylscopolaminebromide, 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.

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.

It is marketed under the trade name Buscopan.[2] It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[3]

Medical uses[edit]

Butylscopolamine is used to treat cramping abdominal pain with some success.[4]

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.[5]

Abuse[edit]

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

References[edit]

  1. ^ Murakami, M.; Tomiyama, Y.; Hayakawa, K.; Akahane, M.; Ajisawa, Y.; Park, Y. C.; Ohnishi, N.; Sugiyama, T.; Kurita, T. (2000). "Effects of β-Adrenergic Stimulation on the Acutely Obstructed Ureter in Dogs" (pdf). Journal of Pharmacology and Experimental Therapeutics 292 (1): 67–75. PMID 10604932. 
  2. ^ http://www.buscopan.com.br/produtos/buscopan-composto.html
  3. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  4. ^ Tytgat, G. N. (2007). "Hyoscine Butylbromide: A Review of its Use in the Treatment of Abdominal Cramping and Pain". Drugs 67 (9): 1343–1357. doi:10.2165/00003495-200767090-00007. PMID 17547475. 
  5. ^ Samuels, L. A.; Christie, L.; Roberts-Gittens, B.; Fletcher, H.; Frederick, J. (2007). "The effect of hyoscine butylbromide on the first stage of labour in term pregnancies". BJOG 114 (12): 1542–1546. doi:10.1111/j.1471-0528.2007.01497.x. PMID 17903230. 

External links[edit]