Hyoscine butylbromide

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Hyoscine butylbromide
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
Routes of
administration
By mouth, rectal, intravenous
Legal status
Legal status
Pharmacokinetic data
Bioavailability <1%
Protein binding Low
Biological half-life 5 hours
Excretion Renal (50%)[citation needed] and fecal
Identifiers
CAS Number 149-64-4 YesY
ATC code A03BB01 (WHO)
PubChem CID 160883
DrugBank DB09300 YesY
ChemSpider 16736107 YesY
UNII 2Z3E1OF81V YesY
ChEMBL CHEMBL1256901 N
Chemical data
Formula C21H30NO4+
Molar mass 360.467 g/mol
 NYesY (what is this?)  (verify)

Hyoscine butylbromide, also known as scopolamine butylbromide[1] and sold under the brandname Buscopan,[2] is a medication used to treat crampy abdominal pain, renal colic, and bladder spasms.[2][3] It is also used to improve a death rattle at the end of life.[4] Hyoscine butylbromide can be taken by mouth, injection into a muscle, or into a vein.[2]

Side effects may include sleepiness, vision changes, triggering of glaucoma, and severe allergies.[2] Sleepiness however, is uncommon.[5] It is unclear if it is safe in pregnancy.[2] It is an anticholinergic agent,[2] which does not have much effect on the brain.[6]

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.[7] It is not available in the United States.[8] The wholesale cost in the developing world is 0.004 to 0.11 USD per pill as of 2014.[9] It is manufactured from hyoscine which is naturally from the plant deadly nightshade.[10]

Medical uses[edit]

Buscopan

Hyoscine butylbromide is effective in treating crampy abdominal pain.[11]

Hyoscine butylbromide is effective in reducing the duration of the first stage of labour, and it is not associated with any obvious adverse outcomes in mother or neonate.[12]

It is also used during abdominal or pelvic MRI or CT scans to improve the quality of pictures.[13]

Pharmacology[edit]

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[edit]

Hyoscine butylbromide is not centrally active and has a low incidence of abuse.[citation needed]

References[edit]

  1. ^ Juo, Pei-Show (2001). Concise Dictionary of Biomedicine and Molecular Biology. (2nd ed.). Hoboken: CRC Press. p. 570. ISBN 9781420041309. 
  2. ^ a b c d e f "Buscopan Tablets and Ampoules". Therapeutic Goods Administration, Australia. 8 November 2010. Retrieved 22 October 2013. 
  3. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 270. ISBN 9781284057560. 
  4. ^ Paice, Judith (2015). Care of the Imminently Dying. Oxford University Press. p. 43. ISBN 9780190244309. 
  5. ^ Handbook of Palliative Care (3rd ed.). New York: Wiley. 2012. p. 570. ISBN 9781118426814. 
  6. ^ Hanks, Geoffrey (2011). Oxford textbook of palliative medicine (4th ed.). Oxford [etc.]: Oxford University Press. p. 805. ISBN 9780199693146. 
  7. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  8. ^ Territo, editor, Dennis A. Casciato ; associate editor, Mary C. (2012). Manual of clinical oncology (7th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins Health. p. 146. ISBN 9781451115604. 
  9. ^ "Hyoscine Butylbromide". International Drug Price Indicator Guide. Retrieved 4 December 2015. 
  10. ^ Twycross, Robert (2003). Introducing palliative care (4th ed.). Oxford: Radcliffe Medical Press. p. 172. ISBN 9781857759150. 
  11. ^ 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. 
  12. ^ 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. 
  13. ^ "Hyoscine butylbromide (Buscopan®)" (PDF). UK: Guy's and St Thomas' NHS Foundation Trust. July 2014. Retrieved 16 June 2016.