BUTYLSCOPOLAMINE

Possibly Marketed Outside US

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 Search

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

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17547475	Antagonist 2778
Muscarinic receptor M2 and M3 4 Target ID: CHEMBL2111347 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17547475	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Spasm of the gastrointestinal tract 2 Sources: https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-07866-3&d=2016092316114622483	Palliative		Approved 8429	BUSCOPAN Approved Use Spasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. Launch Date 1.26947518E12
Renal spasm 2 Sources: https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-07866-3&d=2016092316114622483	Palliative		Approved 8429	BUSCOPAN Approved Use Spasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. Launch Date 1.26947518E12

PubMed

Title	Date	PubMed
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	11495349
Factors that affect the variability in heart rate during endoscopic retrograde cholangiopancreatography.	2002	12666694
Sensory-motor responses to volume-controlled duodenal distension.	2002 Aug	12213104
Randomized trial of trigger point injection for renal colic.	2002 Sep	12410926
Effect of subcutaneous butylscopolamine administration in the reduction of peristaltic artifacts in 1.5-T MR fast abdominal examinations.	2003 Feb	12598993
Sensory and biomechanical responses to ramp-controlled distension of the human duodenum.	2003 Mar	12431908
A new measurement of oesophago-gastric junction competence.	2004 Oct	15500510
Drug specificity and intestinal membrane localization of human organic cation transporters (OCT).	2005 Dec 5	16263091
Apical uptake of choline and cationic drugs in epithelial cell lines derived from human placenta.	2005 Feb-Mar	15708119
Statistical modeling of the response characteristics of mechanosensitive stimuli in the human esophagus.	2005 Jul	15993824
Sensation and distribution of stress and deformation in the human oesophagus.	2006 Feb	16420288
Multimodal pain stimulations in patients with grade B oesophagitis.	2006 Jul	16091554
Ultrasonographic study of mechanosensory properties in human esophagus during mechanical distension.	2006 Jul 28	16874864
Central sensitization in patients with non-cardiac chest pain: a clinical experimental study.	2006 Jun	16754535
Mechanosensory properties in the human gastric antrum evaluated using B-mode ultrasonography during volume-controlled antral distension.	2006 May	16293656
Central neuronal mechanisms of gastric electrical stimulation in diabetic gastroparesis.	2008	18609155
Anticipation of distress after discontinuation of mechanical ventilation in the ICU at the end of life.	2008 Sep	18516588
Luciferase activity under direct ligand-dependent control of a muscarinic acetylcholine receptor.	2009 May 18	19450256
Multidisciplinary functional MR imaging for prostate cancer.	2009 Nov-Dec	19885309
Effect of butylscopolamine on image quality in MRI of the prostate.	2010 Jun	20451013

Patents

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 17:18:50 UTC 2023` Edited by `admin` on `Fri Dec 15 17:18:50 UTC 2023`
Record UNII	2Z3E1OF81V
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BUTYLSCOPOLAMINE

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