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 hyperplasia 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.

<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 for 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">Diphenhydramine</span> Antihistamine medication

Diphenhydramine (DPH) is an antihistamine and sedative first developed by George Rieveschl and put into commercial use in 1946. It is available as a generic medication, and also sold under the brand name Benadryl among others. In 2021, it was the 242nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.

<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">Pethidine</span> Opioid analgesic

Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a fully synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, in Germany. Pethidine is the prototype of a large family of analgesics including the pethidine 4-phenylpiperidines, the prodines, bemidones, and others more distant, including diphenoxylate and analogues.

<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 those that occur in irritable bowel syndrome (IBS). 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 brand 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, for early puberty, or as part of transgender hormone therapy. It is given by injection into a muscle or under the skin.

<span class="mw-page-title-main">Methocarbamol</span> Medication for musculoskeletal pain

Methocarbamol, sold under the brand name Robaxin among others, is a medication used for short-term musculoskeletal pain. It may be used together with rest, physical therapy, and pain medication. It is less preferred in low back pain. It has limited use for rheumatoid arthritis and cerebral palsy. Effects generally begin within half an hour. It is taken by mouth or injection into a vein.

<span class="mw-page-title-main">Biperiden</span> Group of stereoisomers

Biperiden, sold under the brand name Akineton among others, is a medication used to treat Parkinson disease, certain drug-induced movement disorders and Tourette Syndrome. It is not recommended for tardive dyskinesias. It is taken by mouth, injection into a vein, or muscle.

<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

<span class="mw-page-title-main">Drug injection</span> Method of introducing a drug

Drug injection is a method of introducing a drug into the bloodstream via a hollow hypodermic needle, which is pierced through the skin into the body. Intravenous therapy, a form of drug injection, is universally practiced in modernized medical care. As of 2004, there were 13.2 million people worldwide who self-administered injection drugs outside of medical supervision, of which 22% are from developed countries.

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">Diffuse esophageal spasm</span> Uncoordinated contractions of the esophagus

Diffuse esophageal spasm (DES), also known as distal esophageal spasm, is a condition characterized by uncoordinated contractions of the esophagus, which may cause difficulty swallowing (dysphagia) or regurgitation. In some cases, it may cause symptoms such as chest pain, similar to heart disease. In many cases, the cause of DES remains unknown.

<span class="mw-page-title-main">Mebeverine</span> Chemical compound

Mebeverine is a drug used to alleviate some of the symptoms of irritable bowel syndrome. It works by relaxing the muscles in and around the gut.

<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 acetylcholine receptor antagonist, also simply known as a muscarinic antagonist or as an antimuscarinic agent, is a type of anticholinergic drug that blocks the activity of the muscarinic acetylcholine receptors (mAChRs). The muscarinic receptors are proteins 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.

References

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