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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
Structure of BUTYLSCOPOLAMINE

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

HIDE SMILES / InChI

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

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BUSCOPAN

Approved Use

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

Launch Date

2010
Palliative
BUSCOPAN

Approved Use

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

Launch Date

2010
PubMed

PubMed

TitleDatePubMed
Randomized trial of trigger point injection for renal colic.
2002 Sep
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
The potency of KUL-7211, a selective ureteral relaxant, in isolated canine ureter: comparison with various spasmolytics.
2005 Dec
Drug specificity and intestinal membrane localization of human organic cation transporters (OCT).
2005 Dec 5
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
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
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
Polyp measurement based on CT colonography and colonoscopy: variability and systematic differences.
2010 Jun
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.
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 Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
WHO-VATC QA03DB04
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
WHO-ATC A03DB04
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
WHO-VATC QA03BB01
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID4048145
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
WIKIPEDIA
BUTYLSCOPOLAMINE
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
DAILYMED
2Z3E1OF81V
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
CHEBI
145701
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
HSDB
7642
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
RXCUI
1085787
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C83571
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
SMS_ID
100000086194
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
CAS
7182-53-8
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
FDA UNII
2Z3E1OF81V
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
EVMPD
SUB20624
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY
DRUG BANK
DB09300
Created by admin on Fri Dec 15 17:18:51 GMT 2023 , Edited by admin on Fri Dec 15 17:18:51 GMT 2023
PRIMARY