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. 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 YesY
ATC code A03BB01
PubChem CID 160883
ChemSpider 16736107 YesY
UNII 2Z3E1OF81V YesY
Chemical data
Formula C21H30NO4+
Mol. mass 360.467 g/mol
 YesY (what is this?)  (verify)

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 as Buscapina, Buscopan Compositum). In some countries, Buscopan Plus is instead combined with butylscopolamine and Metamizole (for instance, Brazil),[2] but this combination has been replaced with paracetamol in most of the world after concerns about long term usage of Metamizole causing Agranulocytosis.

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.

Medical uses[edit]

Butylscopolamine is used to treat cramping abdominal pain with some success.[3]

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.[4]

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. ^ 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. 
  4. ^ 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]