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Hyoscine butylbromide

From Wikipedia, the free encyclopedia
Anticholinergic medication
For the medication used to treat nausea, seeHyoscine hydrobromide.
Pharmaceutical compound
Hyoscine butylbromide
Clinical data
Trade namesBuscopan, others
Other namesscopolamine butylbromide, butylscopolamine bromide (JANJP)
License data
Routes of
administration
By mouth,rectal,intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability<1%
Protein bindingLow
Eliminationhalf-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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.005.223Edit 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 asscopolamine butylbromide[4] and sold under the brand nameBuscopan among others,[5] is ananticholinergic medication used to treatabdominal pain,esophageal spasms,bladder spasms,biliary colic,[6] andrenal colic.[7][8] It is also used to improveexcessive respiratory secretions at theend of life.[9] Hyoscine butylbromide can be taken by mouth,injection into a muscle, orinto a vein.[5]

Side effects may include sleepiness, vision changes, dry mouth, rapid heart rate, triggering ofglaucoma, andsevere allergies.[7] Sleepiness is uncommon.[10] It is unclear if it is safe inpregnancy.[5] It appears safe in breastfeeding.[11] Greater care is recommended in those with heart problems.[12] It is ananticholinergic agent,[5] which does not have much effect on thebrain.[13]

Hyoscine butylbromide was patented in 1950, and approved for medical use in 1951.[14] It is on theWorld Health Organization's List of Essential Medicines.[15] In the United States, it is available only for the medical treatment of horses,[2][16] and the similar compoundmethscopolamine is used in humans instead.[17] It is manufactured fromhyoscine – also known as scopolamine – which occurs naturally in a variety of plants in the nightshade family,Solanaceae,[18] includingdeadly nightshade (Atropa belladonna).[19]

Medical uses

[edit]
A package of injectable buscopan

Hyoscine butylbromide is effective in treating crampyabdominal pain.[20]

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.[21]

It is also used duringabdominal, pelvicMRI,virtual colonoscopy, and double barium contrasted studies to improve the quality of pictures.[22] Hyoscine butylbromide can reduce the peristaltic movement of the intestines and mucosal foldings, thus reducing the movement artifact of the images.[23]

Side effects

[edit]

Since little of the medication crosses theblood-brain barrier, this drug has less effect on thebrain and therefore causes a reduced occurrence of the centrally mediated effects (such asdelusions,somnolence and inhibition of motor functions), which reduces the usefulness of some other anticholinergic drugs.[13]

Hyoscine butylbromide is still capable of affecting thechemoreceptor trigger zone, due to the lack of a well-developed blood-brain barrier in themedulla oblongata, which increases theantiemetic effect it produces via local action on thesmooth muscle of thegastrointestinal tract.[24]

Other side effects includeaccommodation reflex disturbances,tachycardia, dry mouth, nausea; urinary retention, reduced blood pressure;dyshidrosis;[23] other symptoms are dizziness, flushing and immune system disorders (anaphylactic shock, potentially fatal); anaphylactic reactions; dyspnoea; skin reactions and other hypersensitivity reactions. Cautions should be taken for those with untreated glaucoma, heart failure,benign prostatic hyperplasia with urinary retention as hyoscine may exacerbate these conditions.[23]

Pharmacology

[edit]

Hyoscine butylbromide reduces smooth muscle contraction and the production of respiratory secretions. These are normally stimulated by theparasympathetic nervous system, via theneurotransmitteracetylcholine. As anantimuscarinic, hyoscine butylbromide binds to muscarinic acetylcholine receptors, blocking their effect.[25]

It is aquaternary ammonium compound and a semisynthetic derivative ofhyoscine hydrobromide (scopolamine). The attachment of the butyl-bromide moiety effectively prevents the movement of this drug across theblood–brain barrier, effectively minimising undesirablecentral nervous system side effects associated with scopolamine/hyoscine.[25]

Abuse

[edit]

Hyoscine butylbromide is not centrally active and has a low incidence of abuse.[13] In 2015, it was reported that prisoners atWandsworth Prison and other UK prisons were smoking prescribed hyoscine butylbromide, releasing the potenthallucinogenscopolamine.[26][27] There have also been reports of abuse inMashhad Central Prison inIran.[28]

References

[edit]
  1. ^"Hyoscine Butylbromide (AFT Pharmaceuticals Pty Ltd)".Department of Health and Aged Care.Archived from the original on 2023-03-18.
  2. ^ab"Buscopan- n-butylscopolammonium bromide injection".DailyMed. 8 June 2020. Retrieved16 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. ^abcd"Buscopan Tablets and Ampoules". Therapeutic Goods Administration, Australia. 8 November 2010.Archived from the original on 30 March 2017. Retrieved22 October 2013.
  6. ^"Biliary colic and complications from gallstones - BPJ 61 June 2014".bpac.org.nz. Retrieved2024-01-22.
  7. ^ab"Hyoscine butylbromide SXP".www.ebs.tga.gov.au. 3 July 2017. Retrieved15 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. Retrieved11 September 2019.
  12. ^"Hyoscine butylbromide (Buscopan) injection: risk of serious adverse effects in patients with underlying cardiac disease".www.gov.uk. 20 February 2017. Retrieved15 March 2018.hyoscine butylbromide injection should be used with caution in patients with cardiac disease
  13. ^abcHanks 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. Retrieved2024-01-22.
  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.
  20. ^Tytgat GN (2007). "Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain".Drugs.67 (9):1343–57.doi:10.2165/00003495-200767090-00007.PMID 17547475.S2CID 46971321.
  21. ^Samuels LA, Christie L, Roberts-Gittens B, Fletcher H, Frederick J (December 2007). "The effect of hyoscine butylbromide on the first stage of labour in term pregnancies".BJOG.114 (12):1542–6.doi:10.1111/j.1471-0528.2007.01497.x.PMID 17903230.S2CID 71523418.
  22. ^"Hyoscine butylbromide (Buscopan®)"(PDF). UK:Guy's and St Thomas' NHS Foundation Trust. July 2014.Archived(PDF) from the original on 8 August 2016. Retrieved16 June 2016.
  23. ^abcTytgat GN (November 2008). "Hyoscine butylbromide - a review on its parenteral use in acute abdominal spasm and as an aid in abdominal diagnostic and therapeutic procedures".Current Medical Research and Opinion.24 (11):3159–3173.doi:10.1185/03007990802472700.PMID 18851775.S2CID 73316713.
  24. ^Glare P, Miller J, Nikolova T, Tickoo R (12 September 2011)."Treating nausea and vomiting in palliative care: a review".Clinical Interventions in Aging.6:243–59.doi:10.2147/CIA.S13109.PMC 3180521.PMID 21966219.
  25. ^ab"Buscopan 10 mg Tablets - Summary of Product Characteristics (SmPC) - (emc)".www.medicines.org.uk. Retrieved2020-07-22.
  26. ^"Medics warned to review Buscopan prescriptions after prisoners found smoking it".Pulse Today. Archived fromthe original on 2018-02-07. Retrieved2018-02-07.
  27. ^Optimisation, NECS Medicines (2015-07-21)."Misuse of hyoscine butylbromide (Buscopan) |".medicines.necsu.nhs.uk. Retrieved2018-02-07.
  28. ^Jalali F, Afshari R, Babaei A (June 2014). "Smoking crushed hyoscine/scopolamine tablets as drug abuse".Substance Use & Misuse.49 (7):793–7.doi:10.3109/10826084.2014.880178.PMID 24494624.S2CID 25661684.
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