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
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 |
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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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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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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Pain and biomechanical responses to distention of the duodenum in patients with systemic sclerosis. | 2003 May |
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A new measurement of oesophago-gastric junction competence. | 2004 Oct |
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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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Central sensitization in patients with non-cardiac chest pain: a clinical experimental study. | 2006 Jun |
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Ultrasound-determined geometric and biomechanical properties of the human duodenum. | 2006 Sep |
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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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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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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.
Substance Class |
Chemical
Created
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Record UNII |
2Z3E1OF81V
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C29704
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BUTYLSCOPOLAMINE
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C83571
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