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Hyoscine butylbromide

January 10, 2024

For the medication used to treat nausea, see Hyoscine hydrobromide.

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, renal colic.[6][7] It is also used to improve excessive respiratory secretions at the end of life.[8] Hyoscine butylbromide can be taken by mouth, injection into a muscle, or into a vein.[5]

Hyoscine butylbromide
Clinical data
Trade namesBuscopan, others
Other namesscopolamine butylbromide, butylscopolamine bromide (JAN JP)
License data
  • US DailyMed: n-butylscopolammonium_bromide
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
  • 149-64-4 Y
PubChem CID
  • 6852391
DrugBank
  • DBSALT002585 Y
ChemSpider
  • 16736107 Y
UNII
  • 0GH9JX37C8
KEGG
  • D01451
ChEBI
  • CHEBI:32123
ChEMBL
  • ChEMBL1256901 N
CompTox Dashboard (EPA)
  • DTXSID1022718
ECHA InfoCard100.005.223
Chemical and physical data
FormulaC21H30BrNO4+
Molar mass440.378 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 Y
  • Key:HOZOZZFCZRXYEK-HNHWXVNLSA-M Y
 NY (what is this?)  (verify)

Side effects may include sleepiness, vision changes, dry mouth, rapid heart rate, triggering of glaucoma, and severe allergies.[6] Sleepiness is uncommon.[9] It is unclear if it is safe in pregnancy.[5] It appears safe in breastfeeding.[10] Greater care is recommended in those with heart problems.[11] It is an anticholinergic agent,[5] which does not have much effect on the brain.[12]

Hyoscine butylbromide was patented in 1950, and approved for medical use in 1951.[13] It is on the World Health Organization's List of Essential Medicines.[14] It is not available for human use in the United States,[15] and a similar compound methscopolamine may be used instead.[16] It is manufactured from hyoscine, which occurs naturally in the plant deadly nightshade.[17]

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

Medical uses edit

 
A package of injectable buscopan

Hyoscine butylbromide is effective in treating crampy abdominal pain.[18]

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.[19]

It is also used during abdominal, pelvic MRI, virtual colonoscopy, and double barium contrasted studies to improve the quality of pictures.[20] Hyoscine butylbromide can reduce the peristaltic movement of the intestines and mucosal foldings, thus reducing the movement artifact of the images.[21]

Side effects edit

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.[12]

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.[22]

Other side effects include accommodation reflex disturbances, tachycardia, dry mouth, nausea; urinary retention, reduced blood pressure; dyshidrosis;[21] 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.[21]

Pharmacology edit

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.[23]

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.[23]

Abuse edit

Hyoscine butylbromide is not centrally active and has a low incidence of abuse.[12] In 2015, it was reported that prisoners at Wandsworth Prison and other UK prisons were smoking prescribed hyoscine butylbromide, releasing the potent hallucinogen scopolamine.[24][25] There have also been reports of abuse in Mashhad Central Prison in Iran.[26]

See Also edit

References edit

  1. ^ "Hyoscine Butylbromide (AFT Pharmaceuticals Pty Ltd)". Department of Health and Aged Care. 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. Springer Science and Business Media LLC. 67 (9): 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. from the original on 2015-12-08.
  5. ^ a b c d "Buscopan Tablets and Ampoules". Therapeutic Goods Administration, Australia. 8 November 2010. from the original on 30 March 2017. Retrieved 22 October 2013.
  6. ^ a b "Hyoscine butylbromide SXP". www.ebs.tga.gov.au. 3 July 2017. Retrieved 15 March 2018.
  7. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 270. ISBN 9781284057560.
  8. ^ Paice J (2015). Care of the Imminently Dying. Oxford University Press. p. 43. ISBN 9780190244309. from the original on 2015-12-08.
  9. ^ Handbook of Palliative Care (3rd ed.). New York: Wiley. 2012. p. 570. ISBN 9781118426814. from the original on 2015-12-08.
  10. ^ "Hyoscine" (PDF). www.kemh.health.wa.gov.au. Retrieved 11 September 2019.
  11. ^ "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
  12. ^ a b c Hanks G (2011). Oxford textbook of palliative medicine (4th ed.). Oxford [etc.]: Oxford University Press. p. 805. ISBN 9780199693146. from the original on 2015-12-08.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 446. ISBN 9783527607495.
  14. ^ 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.
  15. ^ 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. from the original on 2015-12-08.
  16. ^ Satoskar RS, Rege SD, Bhandarkar NN (1973). Pharmacology and Pharmacotherapeutics. Popular Prakashan. p. 296. ISBN 9788179915271.
  17. ^ Twycross R (2003). Introducing palliative care (4th ed.). Oxford: Radcliffe Medical Press. p. 172. ISBN 9781857759150. from the original on 2015-12-08.
  18. ^ 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.
  19. ^ 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.
  20. ^ "Hyoscine butylbromide (Buscopan®)" (PDF). UK: Guy's and St Thomas' NHS Foundation Trust. July 2014. (PDF) from the original on 8 August 2016. Retrieved 16 June 2016.
  21. ^ a b c Tytgat 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.
  22. ^ 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.
  23. ^ a b "Buscopan 10 mg Tablets - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 2020-07-22.
  24. ^ . Pulse Today. Archived from the original on 2018-02-07. Retrieved 2018-02-07.
  25. ^ Optimisation, NECS Medicines (2015-07-21). "Misuse of hyoscine butylbromide (Buscopan) |". medicines.necsu.nhs.uk. Retrieved 2018-02-07.
  26. ^ 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.

External links edit

  • "Butylscopolamine bromide". Drug Information Portal. U.S. National Library of Medicine.

January 10, 2024
hyoscine, butylbromide, medication, used, treat, nausea, hyoscine, hydrobromide, also, known, scopolamine, butylbromide, sold, under, brandname, buscopan, among, others, anticholinergic, medication, used, treat, abdominal, pain, esophageal, spasms, bladder, sp. For the medication used to treat nausea see Hyoscine hydrobromide 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 renal colic 6 7 It is also used to improve excessive respiratory secretions at the end of life 8 Hyoscine butylbromide can be taken by mouth injection into a muscle or into a vein 5 Hyoscine butylbromideClinical dataTrade namesBuscopan othersOther namesscopolamine butylbromide butylscopolamine bromide JAN JP License dataUS DailyMed n butylscopolammonium bromideRoutes ofadministrationBy mouth rectal intravenousATC codeA03BB01 WHO A03DB04 WHO QA03BB01 WHO Legal statusLegal statusAU S2 Pharmacy medicine 1 CA OTC Pharmacist only UK General sales list GSL OTC US only 2 In general Over the counter OTC Pharmacokinetic dataBioavailability lt 1 Protein bindingLowElimination half life5 hoursExcretionKidney 50 and fecal 3 IdentifiersIUPAC name 7 S 1a 2b 4b 5a 7b 9 butyl 7 3 hydroxy 1 oxo 2 phenylpropoxy 9 methyl 3 oxa 9 azonitricyclo 3 3 1 02 4 nonaneCAS Number149 64 4 YPubChem CID6852391DrugBankDBSALT002585 YChemSpider16736107 YUNII0GH9JX37C8KEGGD01451ChEBICHEBI 32123ChEMBLChEMBL1256901 NCompTox Dashboard EPA DTXSID1022718ECHA InfoCard100 005 223Chemical and physical dataFormulaC 21H 30Br N O 4 Molar mass440 378 g mol 13D model JSmol Interactive imageSMILES 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 YKey HOZOZZFCZRXYEK HNHWXVNLSA M Y N Y what is this verify Side effects may include sleepiness vision changes dry mouth rapid heart rate triggering of glaucoma and severe allergies 6 Sleepiness is uncommon 9 It is unclear if it is safe in pregnancy 5 It appears safe in breastfeeding 10 Greater care is recommended in those with heart problems 11 It is an anticholinergic agent 5 which does not have much effect on the brain 12 Hyoscine butylbromide was patented in 1950 and approved for medical use in 1951 13 It is on the World Health Organization s List of Essential Medicines 14 It is not available for human use in the United States 15 and a similar compound methscopolamine may be used instead 16 It is manufactured from hyoscine which occurs naturally in the plant deadly nightshade 17 It is available in the United States only for the medical treatment of horses 2 Contents 1 Medical uses 2 Side effects 3 Pharmacology 4 Abuse 5 See Also 6 References 7 External linksMedical uses edit nbsp A package of injectable buscopanHyoscine butylbromide is effective in treating crampy abdominal pain 18 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 19 It is also used during abdominal pelvic MRI virtual colonoscopy and double barium contrasted studies to improve the quality of pictures 20 Hyoscine butylbromide can reduce the peristaltic movement of the intestines and mucosal foldings thus reducing the movement artifact of the images 21 Side effects editSince 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 12 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 22 Other side effects include accommodation reflex disturbances tachycardia dry mouth nausea urinary retention reduced blood pressure dyshidrosis 21 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 21 Pharmacology editHyoscine 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 23 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 23 Abuse editHyoscine butylbromide is not centrally active and has a low incidence of abuse 12 In 2015 it was reported that prisoners at Wandsworth Prison and other UK prisons were smoking prescribed hyoscine butylbromide releasing the potent hallucinogen scopolamine 24 25 There have also been reports of abuse in Mashhad Central Prison in Iran 26 See Also editHyoscine HyoscyamineReferences edit Hyoscine Butylbromide AFT Pharmaceuticals Pty Ltd Department of Health and Aged Care Archived from the original on 2023 03 18 a b Buscopan n butylscopolammonium bromide injection DailyMed 8 June 2020 Retrieved 16 October 2020 Tytgat GN 2007 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 doi 10 2165 00003495 200767090 00007 PMID 17547475 S2CID 46971321 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 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 a b Hyoscine butylbromide SXP www ebs tga gov au 3 July 2017 Retrieved 15 March 2018 Hamilton R 2015 Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab Coat Edition Jones amp Bartlett Learning p 270 ISBN 9781284057560 Paice J 2015 Care of the Imminently Dying Oxford University Press p 43 ISBN 9780190244309 Archived from the original on 2015 12 08 Handbook of Palliative Care 3rd ed New York Wiley 2012 p 570 ISBN 9781118426814 Archived from the original on 2015 12 08 Hyoscine PDF www kemh health wa gov au Retrieved 11 September 2019 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 a b c 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 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 446 ISBN 9783527607495 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 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 amp Wilkins Health p 146 ISBN 9781451115604 Archived from the original on 2015 12 08 Satoskar RS Rege SD Bhandarkar NN 1973 Pharmacology and Pharmacotherapeutics Popular Prakashan p 296 ISBN 9788179915271 Twycross R 2003 Introducing palliative care 4th ed Oxford Radcliffe Medical Press p 172 ISBN 9781857759150 Archived from the original on 2015 12 08 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 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 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 a b c Tytgat 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 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 a b Buscopan 10 mg Tablets Summary of Product Characteristics SmPC emc www medicines org uk Retrieved 2020 07 22 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 Optimisation NECS Medicines 2015 07 21 Misuse of hyoscine butylbromide Buscopan medicines necsu nhs uk Retrieved 2018 02 07 Jalali F Afshari R Babaei A June 2014 Smoking crushed hyoscine scopolamine tablets as drug abuse Substance Use amp Misuse 49 7 793 7 doi 10 3109 10826084 2014 880178 PMID 24494624 S2CID 25661684 External links edit Butylscopolamine bromide Drug Information Portal U S National Library of Medicine Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Hyoscine butylbromide amp oldid 1189164090, wikipedia, wiki, book, books, library,

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