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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30NO4.Br
Molecular Weight 440.3715
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYLSCOPOLAMINE BROMIDE

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.[Br-]

InChI

InChIKey=HOZOZZFCZRXYEK-GSWUYBTGSA-M
InChI=1S/C21H30NO4.BrH/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;1H/q+1;/p-1/t15-,16-,17-,18+,19-,20+,22?;/m1./s1

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

1.26947518E12
Palliative
BUSCOPAN

Approved Use

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

Launch Date

1.26947518E12
PubMed

PubMed

TitleDatePubMed
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
Effect of subcutaneous butylscopolamine administration in the reduction of peristaltic artifacts in 1.5-T MR fast abdominal examinations.
2003 Feb
Sensory and biomechanical responses to ramp-controlled distension of the human duodenum.
2003 Mar
New analysis for the study of the muscle function in the human oesophagus.
2005 Oct
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
Central sensitization in patients with non-cardiac chest pain: a clinical experimental study.
2006 Jun
Ultrasound-determined geometric and biomechanical properties of the human duodenum.
2006 Sep
In vitro effects of PDE5 inhibitors sildenafil, vardenafil and tadalafil on isolated human ureteral smooth muscle: a basic research approach.
2007 Feb
Deterioration of muscle function in the human esophagus with age.
2008 Dec
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
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 21:07:52 UTC 2021
Edited
by admin
on Fri Jun 25 21:07:52 UTC 2021
Record UNII
0GH9JX37C8
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTYLSCOPOLAMINE BROMIDE
Common Name English
hyoscine-n-butyl bromide
Common Name English
HYOSCINE BUTYLBROMIDE [WHO-DD]
Common Name English
SCOPOLAMINE BUTYLBROMIDE
JAN  
Common Name English
BUSCOLAMIN
Brand Name English
SCOPOLAN
Brand Name English
DONOPON
Brand Name English
BUSCOLYSIN
Brand Name English
SCOPOLAMINE BROMOBUTYLATE
Common Name English
HYOSCINE BUTYLBROMIDE [EP MONOGRAPH]
Common Name English
N-BUTYLSCOPOLAMMONIUM BROMIDE
MI  
Common Name English
SPARICON
Brand Name English
SCOBUTYL
Brand Name English
BUSCAPINA
Brand Name English
BUSCAPINE
Brand Name English
MONOSPAN
Brand Name English
STIBRON
Brand Name English
HBB
Common Name English
AMISEPAN
Brand Name English
HYOSCINE BUTYLBROMIDE
MART.   WHO-DD  
Common Name English
SCOBUREN
Brand Name English
HYOSCINE BUTYLBROMIDE [MART.]
Common Name English
SCOBUTIL
Brand Name English
BUTYLMIN
Brand Name English
SPORAMIN
Brand Name English
JOSCINE
Brand Name English
BUSCOL
Brand Name English
N-BUTYLSCOPOLAMMONIUM BROMIDE [MI]
Common Name English
SCOPOLAMINE N-BUTYLBROMIDE
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-, BROMIDE (1:1),(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.)-
Common Name English
TIRANTIL
Brand Name English
BUTYLSCOPOLAMINE BROMIDE [GREEN BOOK]
Common Name English
BUSCOPAN
Brand Name English
SCOBRON
Brand Name English
SCOBRO
Brand Name English
SCOPOLAMINE BUTYLBROMIDE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
NCI_THESAURUS C29698
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
Code System Code Type Description
DRUG CENTRAL
458
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-744-1
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
DRUG BANK
DB09300
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
RXCUI
1851
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY RxNorm
EVMPD
SUB14154MIG
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
NCI_THESAURUS
C65277
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
EPA CompTox
149-64-4
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
MERCK INDEX
M2861
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1618102
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
CAS
149-64-4
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
FDA UNII
0GH9JX37C8
Created by admin on Fri Jun 25 21:07:52 UTC 2021 , Edited by admin on Fri Jun 25 21:07:52 UTC 2021
PRIMARY
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