Chemistry:Hyoscine butylbromide

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Short description: Anticholinergic medication
Hyoscine butylbromide
Butylscopolamine skeletal.svg
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC21H30BrNO4+
Molar mass440.378 g·mol−1
3D model (JSmol)
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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] Despite its name, there is no bromine in hyoscine butylbromide.

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

Medical uses

A package of injectable buscopan

Hyoscine butylbromide is effective in treating crampy abdominal 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 during abdominal, pelvic MRI, 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

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

Hyoscine butylbromide is still capable of affecting the chemoreceptor trigger zone, due to the lack of a well-developed blood-brain barrier in the medulla oblongata, which increases the antiemetic effect it produces via local action on the smooth muscle of the gastrointestinal tract.[24]

Other side effects include accommodation 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 hypertrophy with urinary retention as hyoscine may exacerbates these conditions.[23]

Pharmacology

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

It is a quaternary ammonium compound and a semisynthetic derivative of hyoscine hydrobromide (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.[25]

Abuse

Hyoscine butylbromide is not centrally active and has a low incidence of abuse.[13] In 2015, it was reported that prisoners at Wandsworth Prison and other UK prisons were smoking prescribed hyoscine butylbromide, releasing the potent hallucinogen scopolamine.[26][27] There have also been reports of abuse in Mashhad Central Prison in Iran.[28]

See also

References

  1. ↑ "Hyoscine Butylbromide (AFT Pharmaceuticals Pty Ltd)". https://www.tga.gov.au/resources/prescription-medicines-registrations/hyoscine-butylbromide-aft-pharmaceuticals-pty-ltd. 
  2. ↑ 2.0 2.1 "Buscopan- n-butylscopolammonium bromide injection". 8 June 2020. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=858926e9-457e-47c2-b7c4-2d1c6bb13ea8. 
  3. ↑ "Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain". Drugs (Springer Science and Business Media LLC) 67 (9): 1343–1357. 2007. doi:10.2165/00003495-200767090-00007. PMID 17547475. 
  4. ↑ Concise Dictionary of Biomedicine and Molecular Biology. (2nd ed.). Hoboken: CRC Press. 2001. p. 570. ISBN 9781420041309. https://books.google.com/books?id=Y4DLBQAAQBAJ&pg=PA570. 
  5. ↑ 5.0 5.1 5.2 5.3 "Buscopan Tablets and Ampoules". Therapeutic Goods Administration, Australia. 8 November 2010. https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-07866-3. 
  6. ↑ "Biliary colic and complications from gallstones - BPJ 61 June 2014". https://bpac.org.nz/bpj/2014/june/gallstones.aspx. 
  7. ↑ 7.0 7.1 "Hyoscine butylbromide SXP". 3 July 2017. https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2017-PI-02633-1. 
  8. ↑ Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. 2015. p. 270. ISBN 9781284057560. 
  9. ↑ Care of the Imminently Dying. Oxford University Press. 2015. p. 43. ISBN 9780190244309. https://books.google.com/books?id=QCTYCgAAQBAJ&pg=PT43. 
  10. ↑ Handbook of Palliative Care (3rd ed.). New York: Wiley. 2012. p. 570. ISBN 9781118426814. https://books.google.com/books?id=aXP4_H9OX_AC&pg=PT570. 
  11. ↑ "Hyoscine". https://www.kemh.health.wa.gov.au/~/media/Files/Hospitals/WNHS/For%20health%20professionals/Clinical%20guidelines/Pharmacy/medications/hyoscine_butylbromide.pdf. 
  12. ↑ "Hyoscine butylbromide (Buscopan) injection: risk of serious adverse effects in patients with underlying cardiac disease". 20 February 2017. https://www.gov.uk/drug-safety-update/hyoscine-butylbromide-buscopan-injection-risk-of-serious-adverse-effects-in-patients-with-underlying-cardiac-disease. "hyoscine butylbromide injection should be used with caution in patients with cardiac disease" 
  13. ↑ 13.0 13.1 13.2 Oxford textbook of palliative medicine (4th ed.). Oxford [etc.]: Oxford University Press. 2011. p. 805. ISBN 9780199693146. https://books.google.com/books?id=Fk9uBAAAQBAJ&pg=PA805. 
  14. ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 446. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA446. 
  15. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  16. ↑ "Supportive Care". Manual of Clinical Oncology (7th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins Health. 2012. p. 146. ISBN 9781451115604. https://books.google.com/books?id=4ggoPDgZx2YC&pg=PA146. 
  17. ↑ (in en) Pharmacology and Pharmacotherapeutics. Popular Prakashan. 1973. p. 296. ISBN 9788179915271. https://books.google.com/books?id=7d493VOD4P8C&pg=PA296. 
  18. ↑ "Scopolamine | Anticholinergic, Hyoscine, Motion Sickness | Britannica" (in en). https://www.britannica.com/science/scopolamine. 
  19. ↑ Introducing palliative care (4th ed.). Oxford: Radcliffe Medical Press. 2003. p. 172. ISBN 9781857759150. https://books.google.com/books?id=YmMwVnGTNiYC&pg=PA172. 
  20. ↑ "Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain". Drugs 67 (9): 1343–57. 2007. doi:10.2165/00003495-200767090-00007. PMID 17547475. 
  21. ↑ "The effect of hyoscine butylbromide on the first stage of labour in term pregnancies". BJOG 114 (12): 1542–6. December 2007. doi:10.1111/j.1471-0528.2007.01497.x. PMID 17903230. 
  22. ↑ "Hyoscine butylbromide (Buscopan®)". UK: Guy's and St Thomas' NHS Foundation Trust. July 2014. http://www.guysandstthomas.nhs.uk/resources/patient-information/radiology/hyoscine-butylbromide-buscopan.pdf. 
  23. ↑ 23.0 23.1 23.2 "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. November 2008. doi:10.1185/03007990802472700. PMID 18851775. 
  24. ↑ "Treating nausea and vomiting in palliative care: a review". Clinical Interventions in Aging 6: 243–59. 12 September 2011. doi:10.2147/CIA.S13109. PMID 21966219. 
  25. ↑ 25.0 25.1 "Buscopan 10 mg Tablets - Summary of Product Characteristics (SmPC) - (emc)". https://www.medicines.org.uk/emc/product/1775/smpc. 
  26. ↑ "Medics warned to review Buscopan prescriptions after prisoners found smoking it" (in en). Pulse Today. http://www.pulsetoday.co.uk/clinical/prescribing/medics-warned-to-review-buscopan-prescriptions-after-prisoners-found-smoking-it/20020097.article. 
  27. ↑ Optimisation, NECS Medicines (2015-07-21). "Misuse of hyoscine butylbromide (Buscopan) |" (in en-GB). http://medicines.necsu.nhs.uk/misuse-of-hyoscine-butylbromide-buscopan/. 
  28. ↑ "Smoking crushed hyoscine/scopolamine tablets as drug abuse". Substance Use & Misuse 49 (7): 793–7. June 2014. doi:10.3109/10826084.2014.880178. PMID 24494624. 

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