Butylscopolaminium bromide
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| Surname | Butylscopolaminium bromide | |||||||||||||||||||||
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| Molecular formula | C 21 H 30 BrNO 4 | |||||||||||||||||||||
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| Molar mass | 440.37 g · mol -1 | |||||||||||||||||||||
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firmly |
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| Melting point |
142-144 ° C |
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Easily soluble in water and dichloromethane , slightly soluble in anhydrous ethanol |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||||||||
Narcotic analgesics (more precisely N -Butylscopolaminiumbromid), also butylscopolaminium bromide or shortly butylscopolamine , is a drug selected from the group of parasympatholytics . It blocks the muscarinic acetylcholine receptor and thus belongs to the muscarinic receptor antagonists. As a result, the drug has an antispasmodic effect and is used as a spasmolytic .
Butylscopolaminium bromide has been on the WHO list of essential drugs since 2013 .
Pharmacological properties
Butylscopolaminium bromide has a motility- reducing effect on the smooth muscles ; the pharmacological effect lasts for several hours. The therapeutic effectiveness of this medicinal substance can be observed directly during gastroscopy : after intravenous administration, an increased, disturbing peristalsis of the stomach comes to a standstill within one to two minutes .
As a hydrophilic quaternary ammonium compound , the active ingredient is only poorly absorbed from the gastrointestinal tract (absorption rate: <1%). The half-life of the active substance is 5.1 hours.
Clinical information
N- Butylscopolaminium bromide can be administered orally (e.g. as a tablet or dragee ), rectally (as a suppository ) or intravenously . It is indicated for the treatment of cramp-like complaints ( spasms ) in the stomach and intestines, the biliary tract, the lower urinary tract and the female sexual organs, and also to facilitate endoscopic examinations. It is also used in palliative medicine to alleviate so-called rattle breathing in the dying. The application is usually intravenous, subcutaneous or intramuscular .
Orally or rectally, N- butylscopolaminium bromide is used for mild to moderate spasms of the gastrointestinal tract . Despite the low rate of absorption, a number of placebo- controlled double-blind studies show the therapeutic effectiveness of N- butylscopolaminium bromide when administered orally and rectally. This is particularly well documented for spastic complaints in irritable bowel syndrome (Colon irritabile). Systemic absorption is of minor importance for the therapeutic effect in the gastrointestinal tract , since a local mechanism of action, starting from the lumen of the digestive organs on nicotinic and muscarinic acetylcholine receptors in the muscle layer of the gastrointestinal tract, plays the decisive role.
Side effects and contraindications
A large part of the side effects is due to the anticholinergic effects of butylscopolamine bromide. Side effects of all antispasmodics (anticonvulsant drugs ) can include reddening of the skin, bloating , constipation , visual disturbances, reduced perspiration , rapid heartbeat ( tachycardia ), accommodation disorders and a dry mouth.
They should not be used with increased intraocular pressure ( glaucoma or glaucoma), bladder emptying disorders , intestinal obstruction due to foreign bodies or intestinal obstruction or cardiac arrhythmias .
In contrast to the parent substance scopolamine , N- butylscopolaminium bromide usually does not penetrate the intact blood-brain barrier and therefore does not generally cause any central side effects.
Other Information
Extraction
N -Butylscopolaminium bromide is a semi-synthetic derivative of the plant alkaloid scopolamine . It is produced by N -alkylation of (-) - scopolamine using 1-butyl bromide in acetonitrile. The starting material scopolamine is used for pharmaceutical production from parts of plants such. B. won from Datura (thorn apple), Brugmansia (angel's trumpet) or Duboisia .
Combination preparations
Butylscopolaminium bromide can be combined with pain relievers such as paracetamol or metamizol fix. However, combinations with metamizole for human medical use have not been marketable in Germany since 1987, after the Federal Health Office responsible at the time classified metamizole-containing combination drugs as questionable. Such combinations ( Buscopan compositum ) are also banned in the USA, Australia, Japan and most European countries , but not in Brazil ( Buscopan composto ).
Trade names
Monopreparations Buscopan (D, A, CH), Buscapina (A), Buscofen (I), Spasman (D) as well as generic combination preparations
- with paracetamol : Buscopan plus (D, A), Buscopina plus (A)
- with metamizole ( veterinary medicinal product ): Buscopan compositum (D, A), Buscosol (D), Spasmium comp. (D)
Regulation at the expense of health insurance companies in Germany
Butylscopolamine does not require a prescription for oral use in Germany and is therefore not reimbursable for adults by the statutory health insurance companies . According to a ruling by the Federal Social Court in May 2014, however, if there are severe or very severe spastic abdominal complaints, it must be checked in individual cases whether exceptions should be permitted.
Web links
- Entry on butylscopolamine at Vetpharm
literature
- Ernst Mutschler u. a .: drug effects . 8th edition. Scientific publishing company. Stuttgart 2001. ISBN 3-8047-1763-2 .
- J. Hotz et al .: Consensus report: Irritable bowel syndrome - definition, confirmation of diagnosis, pathophysiology and therapy options - consensus of the German Society for Digestive and Metabolic Diseases. In: Z. Gastroenterol. 37, 1999, 685-700 (on- line ).
- A. Wichert: Recognize and treat irritable bowel syndrome. In: DAZ 143 (47). 2003, 1-8.
Individual evidence
- ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 259.
- ↑ European Pharmacopoeia, 8th edition (official German edition), Grundwerk 2014, p. 2585: "Butylscopolaminiumbromid".
- ↑ a b butylscopolaminium bromide data sheet from Sigma-Aldrich , accessed on March 14, 2011 ( PDF ).
- ↑ Data sheet HYOSCINE BUTYLBROMIDE CRS (PDF) at EDQM , accessed on June 5, 2009.
- ↑ a b c A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th Edition Thieme 2001, ISBN 3-13-115134-X .
- ↑ "Internal Medicine" Gerd Herold, 2012.
- ↑ DE 856 890 (Boehringer Ingelheim), appl. 1950.
- ↑ Deutsches Ärzteblatt - Announcement of the Drugs Commission of the German Medical Association: Sales stop for 62 metamizole-containing combination pain relievers (PDF; 54 kB), May 7, 1987.
- ↑ report mainz: Boehringer Ingelheim wants to resell controversial drug , October 23, 2012.
- ↑ Judgment of the Federal Social Court of May 14, 2014 File number: B 6 KA 21/13 R, media information of the Federal Social Court No. 11/14 of May 15, 2014 .
