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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30NO4.Br
Molecular Weight 440.371
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYLSCOPOLAMINE BROMIDE

SMILES

[Br-].[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=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 C21H29NO4
Molecular Weight 359.4593
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

CNS Non-penetrant
1014
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

Boehringer Ingelheim
131
Curator's Comment: Boehringer Ingelheim first launched Buscopan in the early 1950s in Egipt

Approval Year

2004
210
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
BUSCOPAN

Approved Use

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

Launch Date

1.26947518E12
Palliative
Approved
8429
BUSCOPAN

Approved Use

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

Launch Date

1.26947518E12
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
Factors that affect the variability in heart rate during endoscopic retrograde cholangiopancreatography.
2002
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
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
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
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
Multimodal pain stimulations in patients with grade B oesophagitis.
2006 Jul
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
Ultrasound-determined geometric and biomechanical properties of the human duodenum.
2006 Sep
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
Central neuronal mechanisms of gastric electrical stimulation in diabetic gastroparesis.
2008
Deterioration of muscle function in the human esophagus with age.
2008 Dec
High-resolution T2-weighted abdominal magnetic resonance imaging using respiratory triggering: impact of butylscopolamine on image quality.
2008 May
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
Multidisciplinary functional MR imaging for prostate cancer.
2009 Nov-Dec
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

US3509200
2

Sample Use Guides

In Vivo Use Guide
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
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 Dec 15 16:38:28 UTC 2023
Edited
by admin
on Fri Dec 15 16:38:28 UTC 2023
Record UNII
0GH9JX37C8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTYLSCOPOLAMINE BROMIDE
Common Name English
hyoscine-n-butyl bromide
Common Name English
SCOPOLAMINE BUTYLBROMIDE
JAN  
Common Name English
BUSCOLAMIN
Brand Name English
SCOPOLAN
Brand Name English
Hyoscine butylbromide [WHO-DD]
Common 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 Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
Code System Code Type Description
DRUG CENTRAL
458
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-744-1
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
DRUG BANK
DB09300
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
RXCUI
1851
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY RxNorm
CHEBI
32123
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
EVMPD
SUB14154MIG
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
NCI_THESAURUS
C65277
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
SMS_ID
100000093055
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
WIKIPEDIA
Hyoscine butylbromide
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID1022718
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
MERCK INDEX
m2861
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1618102
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
CAS
149-64-4
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
FDA UNII
0GH9JX37C8
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
DAILYMED
0GH9JX37C8
Created by admin on Fri Dec 15 16:38:28 UTC 2023 , Edited by admin on Fri Dec 15 16:38:28 UTC 2023
PRIMARY
Related Record Type Details
Structure of BUTYLSCOPOLAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of TROPIC ACID
IMPURITY -> PARENT
Related Record Type Details
Structure of BUTYLSCOPOLAMINE
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