Hyoscine butylbromide

Last updated
Hyoscine butylbromide
Butylscopolamine skeletal with bromide.svg
Clinical data
Trade names Buscopan, 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 binding Low
Elimination half-life 5 hours
Excretion Kidney (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 InfoCard 100.005.223 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H30BrNO4+
Molar mass 440.378 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 Yes check.svgY
  • Key:HOZOZZFCZRXYEK-HNHWXVNLSA-M Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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]

Medical uses

A package of injectable buscopan Butylscopolamine.jpg
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 exacerbate 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]

Related Research Articles

<span class="mw-page-title-main">Scopolamine</span> Tropane alkaloid & anticholinergic drug

Scopolamine, also known as hyoscine, or Devil's Breath, is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is used as a medication to treat motion sickness and postoperative nausea and vomiting. It is also sometimes used before surgery to decrease saliva. When used by injection, effects begin after about 20 minutes and last for up to 8 hours. It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability.

<span class="mw-page-title-main">Atropine</span> Anticholinergic medication used as antidote for nerve agent poisoning

Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.

An antiemetic is a drug that is effective against vomiting and nausea. Antiemetics are typically used to treat motion sickness and the side effects of opioid analgesics, general anaesthetics, and chemotherapy directed against cancer. They may be used for severe cases of gastroenteritis, especially if the patient is dehydrated.

<span class="mw-page-title-main">Haloperidol</span> Typical antipsychotic medication

Haloperidol, sold under the brand name Haldol among others, is a typical antipsychotic medication. Haloperidol is used in the treatment of schizophrenia, tics in Tourette syndrome, mania in bipolar disorder, delirium, agitation, acute psychosis, and hallucinations from alcohol withdrawal. It may be used by mouth or injection into a muscle or a vein. Haloperidol typically works within 30 to 60 minutes. A long-acting formulation may be used as an injection every four weeks by people with schizophrenia or related illnesses, who either forget or refuse to take the medication by mouth.

<span class="mw-page-title-main">Hyoscyamine</span> Tropane alkaloid

Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

<span class="mw-page-title-main">Abdominal pain</span> Stomach aches

Abdominal pain, also known as a stomach ache, is a symptom associated with both non-serious and serious medical issues. Since the abdomen contains most of the body's vital organs, it can be an indicator of a wide variety of diseases. Given that, approaching the examination of a person and planning of a differential diagnosis is extremely important.

<span class="mw-page-title-main">Dicycloverine</span> Antispasmodic agent

Dicycloverine, also known as dicyclomine, sold under the brand name Bentyl among others, is a medication that is used to treat spasms of the intestines such as occur in irritable bowel syndrome. It is taken by mouth or by injection into a muscle. While it has been used in baby colic and enterocolitis, evidence does not support these uses.

<span class="mw-page-title-main">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the trade name Atrovent among others, is a type of anticholinergic medication which is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

Hyoscine is a medication used to treat motion sickness and postoperative nausea and vomiting.

<span class="mw-page-title-main">Leuprorelin</span> Manufactured (artificial) injectable hormone

Leuprorelin, also known as leuprolide, is a manufactured version of a hormone used to treat prostate cancer, breast cancer, endometriosis, uterine fibroids, as part of transgender hormone therapy, for early puberty, or to perform chemical castration of violent sex offenders. It is given by injection into a muscle or under the skin.

<span class="mw-page-title-main">Deliriant</span> Class of psychoactive drugs

Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics such as LSD and dissociatives such as ketamine, due to their primary effect of causing delirium, as opposed to the more lucid and less disturbed states produced by other types of hallucinogens. The term generally refers to anticholinergic drugs, which are substances that inhibit the function of the neurotransmitter acetylcholine. Common examples of deliriants include plants of the genera Datura and Brugmansia as well as higher than recommended dosages of diphenhydramine (Benadryl). A number of plant deliriants such as that of the Solanaceae family, particularly in the Americas have been used by some indigenous cultures to reach delirious and altered states for traditions or rituals, such as rites of passage, divination or communicating with the ancestors. Despite their long history of use, deliriants are the least-studied class of hallucinogens in terms of their behavioral and neurological effects.

A death rattle is noisy breathing that often occurs in someone who is near death. It is caused by an accumulation of fluids such as saliva and bronchial secretions in the throat and upper airways. Those who are dying may lose their ability to swallow and may have increased production of bronchial secretions, resulting in such an accumulation. Usually, two or three days earlier, symptoms of approaching death can be observed, such as saliva accumulating in the throat, difficulty taking even a spoonful of water, shortness of breath, and rapid chest movement. While death rattle is a strong indication that someone is near death, it can also be produced by other problems that cause interference with the swallowing reflex, such as brain injuries.

<span class="mw-page-title-main">Methylscopolamine bromide</span> Pharmaceutical drug

Methylscopolamine or methscopolamine, usually provided as the bromide or nitrate salt, is an oral medication used along with other medications to treat peptic ulcers by reducing stomach acid secretion. Proton pump inhibitors and antihistamine medications have made this use obsolete. It can also be used for stomach or intestinal spasms, to reduce salivation, and to treat motion sickness. Methscopolamine is also commonly used as a drying agent, to dry up post-nasal drip, in cold, irritable bowel syndrome and allergy medications

Hypersalivation or hypersialosis is the excessive production of saliva. It has also been defined as increased amount of saliva in the mouth, which may also be caused by decreased clearance of saliva.

<span class="mw-page-title-main">Biliary colic</span> Medical condition in which gallstones cause acute pain

Biliary colic, also known as symptomatic cholelithiasis, a gallbladder attack or gallstone attack, is when a colic occurs due to a gallstone temporarily blocking the cystic duct. Typically, the pain is in the right upper part of the abdomen, and can be severe. Pain usually lasts from 15 minutes to a few hours. Often, it occurs after eating a heavy meal, or during the night. Repeated attacks are common. Cholecystokinin - a gastrointestinal hormone - plays a role in the colic, as following the consumption of fatty meals, the hormone triggers the gallbladder to contract, which may expel stones into the duct and temporarily block it until being successfully passed.

<span class="mw-page-title-main">Muscarinic antagonist</span> Drug that binds to but does not activate muscarinic cholinergic receptors

A muscarinic receptor antagonist (MRA), also called an antimuscarinic, is a type of anticholinergic agent that blocks the activity of the muscarinic acetylcholine receptor. The muscarinic receptor is a protein involved in the transmission of signals through certain parts of the nervous system, and muscarinic receptor antagonists work to prevent this transmission from occurring. Notably, muscarinic antagonists reduce the activation of the parasympathetic nervous system. The normal function of the parasympathetic system is often summarised as "rest-and-digest", and includes slowing of the heart, an increased rate of digestion, narrowing of the airways, promotion of urination, and sexual arousal. Muscarinic antagonists counter this parasympathetic "rest-and-digest" response, and also work elsewhere in both the central and peripheral nervous systems.

Pain in cancer may arise from a tumor compressing or infiltrating nearby body parts; from treatments and diagnostic procedures; or from skin, nerve and other changes caused by a hormone imbalance or immune response. Most chronic (long-lasting) pain is caused by the illness and most acute (short-term) pain is caused by treatment or diagnostic procedures. However, radiotherapy, surgery and chemotherapy may produce painful conditions that persist long after treatment has ended.

<span class="mw-page-title-main">Cancer and nausea</span>

Cancer and nausea are associated in about fifty percent of people affected by cancer. This may be as a result of the cancer itself, or as an effect of the treatment such as chemotherapy, radiation therapy, or other medication such as opiates used for pain relief. About 70 to 80% of people undergoing chemotherapy experience nausea or vomiting. Nausea and vomiting may also occur in people not receiving treatment, often as a result of the disease involving the gastrointestinal tract, electrolyte imbalance, or as a result of anxiety. Nausea and vomiting may be experienced as the most unpleasant side effects of cytotoxic drugs and may result in patients delaying or refusing further radiotherapy or chemotherapy.

Peripherally selective drugs have their primary mechanism of action outside of the central nervous system (CNS), usually because they are excluded from the CNS by the blood–brain barrier. By being excluded from the CNS, drugs may act on the rest of the body without producing side-effects related to their effects on the brain or spinal cord. For example, most opioids cause sedation when given at a sufficiently high dose, but peripherally selective opioids can act on the rest of the body without entering the brain and are less likely to cause sedation. These peripherally selective opioids can be used as antidiarrheals, for instance loperamide (Imodium).

<span class="mw-page-title-main">Cholinergic blocking drug</span> Drug that block acetylcholine in synapses of cholinergic nervous system

Cholinergic blocking drugs are a group of drugs that block the action of acetylcholine (ACh), a neurotransmitter, in synapses of the cholinergic nervous system. They block acetylcholine from binding to cholinergic receptors, namely the nicotinic and muscarinic receptors.

References

  1. ↑ "Hyoscine Butylbromide (AFT Pharmaceuticals Pty Ltd)". Department of Health and Aged Care . Archived from the original on 2023-03-18.
  2. 1 2 "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. 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.
  6. ↑ "Biliary colic and complications from gallstones - BPJ 61 June 2014". bpac.org.nz. Retrieved 2024-01-22.
  7. 1 2 "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. 1 2 3 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.
  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. Retrieved 16 June 2016.
  23. 1 2 3 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.
  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. 1 2 "Buscopan 10 mg Tablets - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 2020-07-22.
  26. ↑ "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.
  27. ↑ Optimisation, NECS Medicines (2015-07-21). "Misuse of hyoscine butylbromide (Buscopan) |". medicines.necsu.nhs.uk. Retrieved 2018-02-07.
  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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