Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H30NO4.Br |
| Molecular Weight | 440.371 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Br-].[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2[N@@+]3(C)CCCC)OC(=O)[C@H](CO)C4=CC=CC=C4
InChI
InChIKey=HOZOZZFCZRXYEK-GSWUYBTGSA-M
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
| Molecular Formula | C21H29NO4 |
| Molecular Weight | 359.4593 |
| Charge | 0 |
| Count |
|
| Stereochemistry | EPIMERIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | BrH |
| Molecular Weight | 80.912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: http://www.boehringer-ingelheim.info/mena/segments/consumer_healthcare/buscopan.html; http://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm118039.pdf; http://www.ncbi.nlm.nih.gov/pubmed/17547475
Curator's Comment: http://www.boehringer-ingelheim.info/mena/segments/consumer_healthcare/buscopan.html; http://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm118039.pdf; http://www.ncbi.nlm.nih.gov/pubmed/17547475
Butylscopolamine (trade name Buscopan) is a peripherally acting antimuscarinic, anticholinergic agent. It is a natural substance extracted from Duboisia plant species as Scopolamine (hyoscine) and chemically modified to the quaternary ammonium compound hyoscine butylbromide. It was first registered in Germany in 1951 and marketed in 1952, and is available worldwide both as a prescription drug and as an over-the-counter medicine in many countries. Buscopan is used to treat spasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. In the United States Buscopan approved by FDA to be used in the veterinary medicine only - for the control of abdominal pain associated with spasmodic colic, flatulent colic, and simple impactions in horses. Butylbromide has a high affinity for muscarinic receptors located on the smooth-muscle cells of the GI tract. Its anticholinergic action exerts a smooth-muscle relaxing/spasmolytic effect. Blockade of the muscarinic receptors in the GI tract is the basis for its use in the treatment of abdominal pain secondary to cramping. Hyoscine butylbromide also binds to nicotinic receptors, which induces a ganglion-blocking effect.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL216 |
|||
Target ID: CHEMBL2111347 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | BUSCOPAN Approved UseSpasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. Launch Date2010 |
|||
| Palliative | BUSCOPAN Approved UseSpasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. Launch Date2010 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Autonomic nervous function in patients with peptic ulcer studied by spectral analysis of heart rate variability. | 2001 |
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| Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists. | 2001 Apr |
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| Effects of isoproterenol and butylscopolamine on the friction between an artificial stone and the intraureteral wall in anesthetized rabbits. | 2001 Sep |
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| Factors that affect the variability in heart rate during endoscopic retrograde cholangiopancreatography. | 2002 |
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| Sensory-motor responses to volume-controlled duodenal distension. | 2002 Aug |
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| Mechanical properties in the human gastric antrum using B-mode ultrasonography and antral distension. | 2002 Aug |
|
| Randomized trial of trigger point injection for renal colic. | 2002 Sep |
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| Safety of nonanesthetist sedation with propofol for outpatient colonoscopy and esophagogastroduodenoscopy. | 2003 Aug |
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| Effect of subcutaneous butylscopolamine administration in the reduction of peristaltic artifacts in 1.5-T MR fast abdominal examinations. | 2003 Feb |
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| Controlled mechanical distension of the human oesophagus: sensory and biomechanical findings. | 2003 Jan |
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| Sensory and biomechanical responses to ramp-controlled distension of the human duodenum. | 2003 Mar |
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| Pain and biomechanical responses to distention of the duodenum in patients with systemic sclerosis. | 2003 May |
|
| [CT-colonography with the 16-slice CT for the diagnostic evaluation of colorectal neoplasms and inflammatory colon diseases]. | 2003 Oct |
|
| Gut mucosal and plasma concentrations of glutamine: a comparison between two enriched enteral feeding solutions in critically ill patients. | 2003 Oct 13 |
|
| A new measurement of oesophago-gastric junction competence. | 2004 Oct |
|
| The potency of KUL-7211, a selective ureteral relaxant, in isolated canine ureter: comparison with various spasmolytics. | 2005 Dec |
|
| Drug specificity and intestinal membrane localization of human organic cation transporters (OCT). | 2005 Dec 5 |
|
| Apical uptake of choline and cationic drugs in epithelial cell lines derived from human placenta. | 2005 Feb-Mar |
|
| Magnetic resonance imaging of the small bowel in Crohn's disease. | 2005 Jul |
|
| Statistical modeling of the response characteristics of mechanosensitive stimuli in the human esophagus. | 2005 Jul |
|
| New analysis for the study of the muscle function in the human oesophagus. | 2005 Oct |
|
| Endoscopic papillary balloon dilation with large balloon after limited sphincterotomy for retrieval of choledocholithiasis. | 2006 Dec 31 |
|
| Sensation and distribution of stress and deformation in the human oesophagus. | 2006 Feb |
|
| Assessment of the gastric emptying velocity by the 13C-octanoate breath test: deconvolution versus a Wagner-Nelson analysis. | 2006 Jul |
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| Multimodal pain stimulations in patients with grade B oesophagitis. | 2006 Jul |
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| Ultrasonographic study of mechanosensory properties in human esophagus during mechanical distension. | 2006 Jul 28 |
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| Central sensitization in patients with non-cardiac chest pain: a clinical experimental study. | 2006 Jun |
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| A case of sudden death after intramuscular injection of butylscopolamine bromide. | 2006 May |
|
| Mechanosensory properties in the human gastric antrum evaluated using B-mode ultrasonography during volume-controlled antral distension. | 2006 May |
|
| Ultrasound-determined geometric and biomechanical properties of the human duodenum. | 2006 Sep |
|
| Geometric and mechanosensory properties of the sigmoid colon evaluated with magnetic resonance imaging. | 2007 Apr |
|
| In vitro effects of PDE5 inhibitors sildenafil, vardenafil and tadalafil on isolated human ureteral smooth muscle: a basic research approach. | 2007 Feb |
|
| Local staging of rectal cancer: the current role of MRI. | 2007 Feb |
|
| Central neuronal mechanisms of gastric electrical stimulation in diabetic gastroparesis. | 2008 |
|
| Deterioration of muscle function in the human esophagus with age. | 2008 Dec |
|
| High-resolution T2-weighted abdominal magnetic resonance imaging using respiratory triggering: impact of butylscopolamine on image quality. | 2008 May |
|
| Anticipation of distress after discontinuation of mechanical ventilation in the ICU at the end of life. | 2008 Sep |
|
| Luciferase activity under direct ligand-dependent control of a muscarinic acetylcholine receptor. | 2009 May 18 |
|
| Multidisciplinary functional MR imaging for prostate cancer. | 2009 Nov-Dec |
|
| 3D gastric computed tomography as a new imaging in patients with failure or complication after bariatric surgery. | 2010 Dec |
|
| A comparison of the effect of intranasal desmopressin and intramuscular hyoscine N-butyl bromide combination with intramuscular hyoscine N-butyl bromide alone in acute renal colic. | 2010 Jul |
|
| [Mydriasis due to accidental use of butylscopolamine]. | 2010 Jul-Aug |
|
| Effect of butylscopolamine on image quality in MRI of the prostate. | 2010 Jun |
|
| Polyp measurement based on CT colonography and colonoscopy: variability and systematic differences. | 2010 Jun |
|
| Neuropharmacology of vestibular system disorders. | 2010 Mar |
Patents
Sample Use Guides
For adults and children over 6 years: 2 Buscopan tablets ( 10 mg each) four times daily or 1x20 mg Buscopan Forte tablet four times daily. Buscopan tablets are not recommended for children under 6 years of age. 1 or 2 ampules (20 or 40 mg) by intramuscular or slow intravenous injection. A maximum daily dose of 100 mg should not be exceeded. BUSCOPAN tablets and ampules should not be taken on a continuous daily basis or for extended periods without investigating the cause of abdominal pain.
Route of Administration:
Other
Hyoscine butylbromide at the concentration range 1 nmol/L-10 umol/L effects on muscle activity were studied with isometric force transducers and calcium imaging and it effects on epithelial secretion were studied with with Ussing chamber technique and on enteric neurons using fast neuroimaging. Hyoscine butylbromide concentration dependently reduced muscle contractions, calcium mobilization, and epithelial secretion induced by the muscarinic agonist bethanechol with IC50 values of 429, 121, and 224 nmol/L, respectively.
| Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:38:28 GMT 2023
by
admin
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Fri Dec 15 16:38:28 GMT 2023
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| Record UNII |
0GH9JX37C8
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29704
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NCI_THESAURUS |
C29698
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458
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205-744-1
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DB09300
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1851
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32123
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SUB14154MIG
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C65277
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100000093055
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Hyoscine butylbromide
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DTXSID1022718
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m2861
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CHEMBL1618102
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149-64-4
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0GH9JX37C8
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0GH9JX37C8
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ACTIVE MOIETY |