Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H30NO4 |
Molecular Weight | 360.4672 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 7 |
E/Z Centers | 0 |
Charge | 1 |
SHOW SMILES / InChI
SMILES
[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=YBCNXCRZPWQOBR-WVHCHWADSA-N
InChI=1S/C21H30NO4/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/q+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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Randomized trial of trigger point injection for renal colic. | 2002 Sep |
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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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Gut mucosal and plasma concentrations of glutamine: a comparison between two enriched enteral feeding solutions in critically ill patients. | 2003 Oct 13 |
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Drug specificity and intestinal membrane localization of human organic cation transporters (OCT). | 2005 Dec 5 |
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Statistical modeling of the response characteristics of mechanosensitive stimuli in the human esophagus. | 2005 Jul |
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Assessment of the gastric emptying velocity by the 13C-octanoate breath test: deconvolution versus a Wagner-Nelson analysis. | 2006 Jul |
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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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[Mydriasis due to accidental use of butylscopolamine]. | 2010 Jul-Aug |
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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A03BB01
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NCI_THESAURUS |
C29704
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WHO-VATC |
QA03DB04
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QA03BB01
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DTXSID4048145
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BUTYLSCOPOLAMINE
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1085787
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C83571
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100000086194
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2Z3E1OF81V
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SUB20624
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DB09300
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)