Hyoscine butylbromide

For the medication used to treat nausea, see Hyoscine hydrobromide.
Hyoscine butylbromide
Names
Trade namesBuscopan, others
Other namesButylscopolamine bromide, scopolamine butylbromide
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
Main usesCrampy abdominal pain, bladder spasms[1][2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Addiction riskLow[3]
Routes of
use		By mouth, rectal, intravenous
Onset of actionWithin 30 min[4]
Duration of actionLess than an hour[4]
Defined daily dose60 mg[5]
Legal
License data
Legal status
Pharmacokinetics
Bioavailability<1%
Protein bindingLow
Elimination half-life5 hours
ExcretionKidney (50%) and fecal[6]
Chemical and physical data
FormulaC21H30BrNO4+
Molar mass440.378 g·mol−1
3D model (JSmol)
SMILES
  • [CCCC[N+]1(C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4)C.[Br-]
InChI
  • 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

Hyoscine butylbromide, also known as scopolamine butylbromide[7] and sold under the brandname Buscopan among others,[8] is a medication used to treat crampy abdominal pain, esophageal spasms, renal colic, and bladder spasms.[1][2] It is also used to improve respiratory secretions at the end of life.[9] It can be taken by mouth, injection into a muscle, or into a vein.[8]

Side effects may include sleepiness, vision changes, dry mouth, rapid heart rate, triggering of glaucoma, and severe allergies.[1] Sleepiness is uncommon.[10] It is unclear if it is safe in pregnancy.[8] It appears safe in breastfeeding.[11] Greater care is recommended in those with heart problems.[12] It is an anticholinergic agent,[8] 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 in the United States,[16] and a similar compound methscopolamine may be used instead.[17] The wholesale cost in the developing world is US$0.004–0.11 per pill as of 2014.[18] It is manufactured from hyoscine which occurs naturally in the plant deadly nightshade.[19]

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 or pelvic MRI or CT scans to improve the quality of pictures.[22]

Dosage

The defined daily dose is 60 mg by mouth, by injection, or rectally.[5] Generally, by mouth, it is taken as 10 to 20 mg per dose up to three or four times per day.[23] By injection doses of 20 to 40 mg may be used up to 100 mg per day.[24]

It may also be used in children, with doses of 5 mg for those 2 to 6 years old and up to 10 mg for those 6 to 12 years old.[25]

Side effects

As little of the medication crosses the blood brain barrier it has less effect on the brain and therefore has reduced occurrence of the centrally mediated effects (such as delusions, somnolence, and inhibition of motor-functions) which hinder the usefulness of some other anticholinergic drugs.[13] Hyoscine butylbromide is still capable of impacting the chemoreceptor trigger zone due to the lack of a well-developed blood-brain-barrier in the medulla oblongata, which potentiates the antiemetic effects that it produces via local action on the smooth muscle of the gastrointestinal tract.[26]

Pharmacology

Hyoscine butylbromide reduces the stimulation of 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.[27]

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.[27]

Misuse

Hyoscine butylbromide is not centrally active and has a low incidence of abuse. In 2015, prisoners at Wandsworth Prison and other UK prisons were smoking prescribed hyoscine butylbromide, releasing the hallucinogen scopolamine.[28][29] There have also been reports of misuse in Mashhad Central Prison in Iran.[30]

References

  1. 1 2 3 "Hyoscine butylbromide SXP". www.ebs.tga.gov.au. 3 July 2017. Archived from the original on 16 March 2018. Retrieved 15 March 2018.
  2. 1 2 Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 270. ISBN 9781284057560.
  3. ↑ Administration, Australian Government Department of Health Therapeutic Goods (6 February 2020). "1.6. Interim decision in relation to hyoscine butylbromide". Therapeutic Goods Administration (TGA). Archived from the original on 29 August 2021. Retrieved 2 September 2020.
  4. 1 2 Woodfield, Georgia; Phillips, Benedict Lyle; Taylor, Victoria; Hawkins, Amy; Stanton, Andrew. Essential Practical Prescribing. John Wiley & Sons. p. 288. ISBN 978-1-118-83773-3. Archived from the original on 2021-08-28. Retrieved 2020-10-31.
  5. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 22 January 2021. Retrieved 30 August 2020.
  6. ↑ Tytgat, Guido N (2007). "Hyoscine Butylbromide". Drugs. Springer Science and Business Media LLC. 67 (9): 1343–1357. doi:10.2165/00003495-200767090-00007. ISSN 0012-6667.
  7. ↑ Juo, Pei-Show (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.
  8. 1 2 3 4 "Buscopan Tablets and Ampoules". Therapeutic Goods Administration, Australia. 8 November 2010. Archived from the original on 30 March 2017. Retrieved 22 October 2013. {{cite journal}}: Cite journal requires |journal= (help)
  9. ↑ Paice, Judith (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. Archived (PDF) from the original on 25 March 2019. 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. Archived from the original on 24 September 2017. Retrieved 15 March 2018. hyoscine butylbromide injection should be used with caution in patients with cardiac disease
  13. 1 2 Hanks, Geoffrey (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, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 446. ISBN 9783527607495. Archived from the original on 2019-03-01. Retrieved 2019-02-28.
  15. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  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. Archived from the original on 2018-06-17. Retrieved 2018-06-16.
  18. ↑ "Hyoscine Butylbromide". International Drug Price Indicator Guide. Archived from the original on 10 May 2017. Retrieved 4 December 2015.
  19. ↑ Twycross, Robert (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.
  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.
  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. Retrieved 16 June 2016.
  23. ↑ "HYOSCINE BUTYLBROMIDE = BUTYLSCOPOLAMINE oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on 28 August 2021. Retrieved 30 August 2020.
  24. ↑ "HYOSCINE BUTYLBROMIDE = BUTYLSCOPOLAMINE injectable - Essential drugs". medicalguidelines.msf.org. Archived from the original on 28 August 2021. Retrieved 2 September 2020.
  25. ↑ "CW Online Formulary". www.pedmed.org. Archived from the original on 19 August 2022. Retrieved 9 August 2022.
  26. ↑ 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.
  27. 1 2 "Buscopan 10 mg Tablets - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Archived from the original on 2020-07-22. Retrieved 2020-07-22.
  28. ↑ "Medics warned to review Buscopan prescriptions after prisoners found smoking it". Pulse Today. Archived from the original on 2018-02-07. Retrieved 2018-02-07.
  29. ↑ Optimisation, NECS Medicines (2015-07-21). "Misuse of hyoscine butylbromide (Buscopan) |". medicines.necsu.nhs.uk. Archived from the original on 2018-02-07. Retrieved 2018-02-07.
  30. ↑ 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.
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