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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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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Magnetic resonance imaging of the small bowel in Crohn's disease. | 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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Sensation and distribution of stress and deformation in the human oesophagus. | 2006 Feb |
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A case of sudden death after intramuscular injection of butylscopolamine bromide. | 2006 May |
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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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Polyp measurement based on CT colonography and colonoscopy: variability and systematic differences. | 2010 Jun |
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)