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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30NO4
Molecular Weight 360.468
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of BUTYLSCOPOLAMINE

SMILES

CCCC[N+]1(C)[C@]2([H])C[C@]([H])(C[C@@]1([H])[C@@]3([H])[C@]2([H])O3)OC(=O)[C@]([H])(CO)c4ccccc4

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

HIDE SMILES / InChI

Molecular Formula C21H29NO4
Molecular Weight 359.4601
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

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

Originator

Curator's Comment:: Boehringer Ingelheim first launched Buscopan in the early 1950s in Egipt

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BUSCOPAN

Approved Use

Spasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology.

Launch Date

1269475200000
Palliative
BUSCOPAN

Approved Use

Spasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology.

Launch Date

1269475200000
PubMed

PubMed

TitleDatePubMed
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
Effects of isoproterenol and butylscopolamine on the friction between an artificial stone and the intraureteral wall in anesthetized rabbits.
2001 Sep
Factors that affect the variability in heart rate during endoscopic retrograde cholangiopancreatography.
2002
Sensory-motor responses to volume-controlled duodenal distension.
2002 Aug
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
Safety of nonanesthetist sedation with propofol for outpatient colonoscopy and esophagogastroduodenoscopy.
2003 Aug
Effect of subcutaneous butylscopolamine administration in the reduction of peristaltic artifacts in 1.5-T MR fast abdominal examinations.
2003 Feb
Controlled mechanical distension of the human oesophagus: sensory and biomechanical findings.
2003 Jan
Sensory and biomechanical responses to ramp-controlled distension of the human duodenum.
2003 Mar
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
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
Multimodal pain stimulations in patients with grade B oesophagitis.
2006 Jul
Ultrasonographic study of mechanosensory properties in human esophagus during mechanical distension.
2006 Jul 28
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
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
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
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

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
by admin
on Fri Jun 25 23:43:11 UTC 2021
Edited
by admin
on Fri Jun 25 23:43:11 UTC 2021
Record UNII
2Z3E1OF81V
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTYLSCOPOLAMINE
HSDB   WHO-DD  
Common Name English
N-BUTYLSCOPOLAMMONIUM CATION
Common Name English
BUTYLSCOPOLAMINE [WHO-DD]
Common Name English
N-BUTYLSCOPOLAMMONIUM
Common Name English
N-BUTYLSCOPOLAMMONIUM ION
Common Name English
BUTYLSCOPOLAMINE [HSDB]
Common Name English
3-OXA-9-AZONIATRICYCLO(3.3.1.0 SUP(2,4))NONANE,9-BUTYL-7-((2S)-3-HYDROXY-1-OXO-2-PHENYLPROPOXY)-9-METHYL-, (1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.)-
Common Name English
Classification Tree Code System Code
WHO-ATC A03BB01
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
WHO-VATC QA03DB04
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
WHO-ATC A03DB04
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
WHO-VATC QA03BB01
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
Code System Code Type Description
EPA CompTox
7182-53-8
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
WIKIPEDIA
BUTYLSCOPOLAMINE
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
HSDB
7642
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
RXCUI
1085787
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C83571
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
CAS
7182-53-8
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
FDA UNII
2Z3E1OF81V
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
EVMPD
SUB20624
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
DRUG BANK
DB09300
Created by admin on Fri Jun 25 23:43:12 UTC 2021 , Edited by admin on Fri Jun 25 23:43:12 UTC 2021
PRIMARY
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