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
DescriptionSources: https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-07866-3&d=2016092316114622483Curator'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
Sources: https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-07866-3&d=2016092316114622483
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.
CNS Activity
Sources: https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-07866-3&d=2016092316114622483
Curator's Comment: As a quaternary ammonium compound with low lipid solubility, it cannot pass the blood/brain barrier easily and only rarely causes the central nervous system side effects associated with atropine and hyoscine
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL216 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17547475 |
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Target ID: CHEMBL2111347 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17547475 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | BUSCOPAN Approved UseSpasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. Launch Date2010 |
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Palliative | BUSCOPAN Approved UseSpasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. Launch Date2010 |
PubMed
Title | Date | PubMed |
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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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A new measurement of oesophago-gastric junction competence. | 2004 Oct |
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The potency of KUL-7211, a selective ureteral relaxant, in isolated canine ureter: comparison with various spasmolytics. | 2005 Dec |
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Drug specificity and intestinal membrane localization of human organic cation transporters (OCT). | 2005 Dec 5 |
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Apical uptake of choline and cationic drugs in epithelial cell lines derived from human placenta. | 2005 Feb-Mar |
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Statistical modeling of the response characteristics of mechanosensitive stimuli in the human esophagus. | 2005 Jul |
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Endoscopic papillary balloon dilation with large balloon after limited sphincterotomy for retrieval of choledocholithiasis. | 2006 Dec 31 |
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Multimodal pain stimulations in patients with grade B oesophagitis. | 2006 Jul |
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Mechanosensory properties in the human gastric antrum evaluated using B-mode ultrasonography during volume-controlled antral distension. | 2006 May |
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Ultrasound-determined geometric and biomechanical properties of the human duodenum. | 2006 Sep |
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Geometric and mechanosensory properties of the sigmoid colon evaluated with magnetic resonance imaging. | 2007 Apr |
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In vitro effects of PDE5 inhibitors sildenafil, vardenafil and tadalafil on isolated human ureteral smooth muscle: a basic research approach. | 2007 Feb |
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Local staging of rectal cancer: the current role of MRI. | 2007 Feb |
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Central neuronal mechanisms of gastric electrical stimulation in diabetic gastroparesis. | 2008 |
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Deterioration of muscle function in the human esophagus with age. | 2008 Dec |
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Anticipation of distress after discontinuation of mechanical ventilation in the ICU at the end of life. | 2008 Sep |
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Multidisciplinary functional MR imaging for prostate cancer. | 2009 Nov-Dec |
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3D gastric computed tomography as a new imaging in patients with failure or complication after bariatric surgery. | 2010 Dec |
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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 |
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[Mydriasis due to accidental use of butylscopolamine]. | 2010 Jul-Aug |
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Effect of butylscopolamine on image quality in MRI of the prostate. | 2010 Jun |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23682729
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.
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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
SUBSTANCE RECORD