Hyoscine butylbromide

For the medication used to treat nausea, see Hyoscine hydrobromide.
Hyoscine butylbromide
Clinical data
Trade namesBuscopan, others
Other namesscopolamine butylbromide, butylscopolamine bromide (JAN JP)
License data
Routes of
administration		By mouth, rectal, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability<1%
Protein bindingLow
Elimination half-life5 hours
ExcretionKidney (50%) and fecal[3]
Identifiers
  • [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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.223 Edit this at Wikidata
Chemical and physical data
FormulaC21H30BrNO4+
Molar mass440.378 g·mol−1
3D model (JSmol)
  • CCCC[N+]1(C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4)C.[Br-]
  • 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 checkY
  • Key:HOZOZZFCZRXYEK-HNHWXVNLSA-M checkY
 ☒NcheckY (what is this?)  (verify)

Hyoscine butylbromide, also known as scopolamine butylbromide[4] and sold under the brandname Buscopan among others,[5] is an anticholinergic medication used to treat abdominal pain, esophageal spasms, bladder spasms, biliary colic,[6] and renal colic.[7][8] It is also used to improve excessive respiratory secretions at the end of life.[9] Hyoscine butylbromide can be taken by mouth, injection into a muscle, or into a vein.[5]

Side effects may include sleepiness, vision changes, dry mouth, rapid heart rate, triggering of glaucoma, and severe allergies.[7] Sleepiness is uncommon.[10] It is unclear if it is safe in pregnancy.[5] It appears safe in breastfeeding.[11] Greater care is recommended in those with heart problems.[12] It is an anticholinergic agent,[5] which does not have much effect on the brain.[13]

Hyoscine butylbromide was patented in 1950, and approved for medical use in 1951.[14] It is on the World Health Organization's List of Essential Medicines.[15] It is not available for human use in the United States,[16] and a similar compound methscopolamine may be used instead.[17] It is manufactured from hyoscine - also known as scopolamine - which occurs naturally in a variety of plants in the nightshade family, Solanaceae,[18] including deadly nightshade (Atropa belladonna).[19]

It is available in the United States only for the medical treatment of horses.[2]

  1. ^ "Hyoscine Butylbromide (AFT Pharmaceuticals Pty Ltd)". Department of Health and Aged Care. Archived from the original on 2023-03-18.
  2. ^ a b "Buscopan- n-butylscopolammonium bromide injection". DailyMed. 8 June 2020. Retrieved 16 October 2020.
  3. ^ Tytgat GN (2007). "Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain". Drugs. 67 (9). Springer Science and Business Media LLC: 1343–1357. doi:10.2165/00003495-200767090-00007. PMID 17547475. S2CID 46971321.
  4. ^ Juo PS (2001). Concise Dictionary of Biomedicine and Molecular Biology (2nd ed.). Hoboken: CRC Press. p. 570. ISBN 9781420041309. Archived from the original on 2015-12-08.
  5. ^ a b c d "Buscopan Tablets and Ampoules". Therapeutic Goods Administration, Australia. 8 November 2010. Archived from the original on 30 March 2017. Retrieved 22 October 2013.
  6. ^ "Biliary colic and complications from gallstones - BPJ 61 June 2014". bpac.org.nz. Retrieved 2024-01-22.
  7. ^ a b "Hyoscine butylbromide SXP". www.ebs.tga.gov.au. 3 July 2017. Retrieved 15 March 2018.
  8. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 270. ISBN 9781284057560.
  9. ^ Paice J (2015). Care of the Imminently Dying. Oxford University Press. p. 43. ISBN 9780190244309. Archived from the original on 2015-12-08.
  10. ^ Handbook of Palliative Care (3rd ed.). New York: Wiley. 2012. p. 570. ISBN 9781118426814. Archived from the original on 2015-12-08.
  11. ^ "Hyoscine" (PDF). www.kemh.health.wa.gov.au. Retrieved 11 September 2019.
  12. ^ "Hyoscine butylbromide (Buscopan) injection: risk of serious adverse effects in patients with underlying cardiac disease". www.gov.uk. 20 February 2017. Retrieved 15 March 2018. hyoscine butylbromide injection should be used with caution in patients with cardiac disease
  13. ^ Hanks G (2011). Oxford textbook of palliative medicine (4th ed.). Oxford [etc.]: Oxford University Press. p. 805. ISBN 9780199693146. Archived from the original on 2015-12-08.
  14. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 446. ISBN 9783527607495.
  15. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  16. ^ Prommer EE, Thompson L, Casciato DA (2012). "Supportive Care". In Casciato DA, Territo MC (eds.). Manual of Clinical Oncology (7th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins Health. p. 146. ISBN 9781451115604. Archived from the original on 2015-12-08.
  17. ^ Satoskar RS, Rege SD, Bhandarkar NN (1973). Pharmacology and Pharmacotherapeutics. Popular Prakashan. p. 296. ISBN 9788179915271.
  18. ^ "Scopolamine | Anticholinergic, Hyoscine, Motion Sickness | Britannica". www.britannica.com. Retrieved 2024-01-22.
  19. ^ Twycross R (2003). Introducing palliative care (4th ed.). Oxford: Radcliffe Medical Press. p. 172. ISBN 9781857759150. Archived from the original on 2015-12-08.