Butylscopolamine

Identification

Name
Butylscopolamine
Accession Number
DB09300
Description

Butylscopolamine is a peripherally acting antimuscarinic, anticholinergic agent. It is used to treat pain and discomfort caused by abdominal cramps, menstrual cramps, or other spasmodic activity in the digestive system. It is also effective at preventing bladder spasms. It is not a pain medication in the normal sense, since it does not directly affect pain, but rather works to prevent painful cramps and spasms from occurring. It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 360.473
Monoisotopic: 360.21693487
Chemical Formula
C21H30NO4
Synonyms
  • butilescopolamina
  • N-butylscopolammonium
  • N-butylscopolammonium cation
  • N-butylscopolammonium ion

Pharmacology

Indication

Used to treat abdmoninal cramping and pain Label.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Scopolamine butylbromide is a muscarinic antagonist which acts to prevent acetylcholine-stimulated contraction of smooth muscle in the gastrointestinal tract 1.

Mechanism of action

Scopolamine butylbromide binds to muscarinic M3 receptors in the gastrointestinal tract 1. This prevents acetycholine from binding to and activating the receptors which would result in contraction of the smooth muscle. The inhibition of contraction reduces spasms and their related pain during abdominal cramping.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
antagonist
Humans
UMuscarinic acetylcholine receptor M2
antagonist
Humans
Absorption

Scopolamine butylbromide has extremely low oral bioavailability with only 0.25-0.82% reaching systemic circulation 1. Peak plasma concentration is reached 0.25-2 hours. Scopolamine butylbromide does not cross the blood brain barrier.

Volume of distribution

The volume of distribution is 128 liters 1.

Protein binding
Not Available
Metabolism

Metabolism occurs mainly through hydrolysis of the ester bond 1. The metabolites are not considered to be significantly active.

Hover over products below to view reaction partners

Route of elimination

Mainly eliminated in the feces (69.7%) with very little in the urine (4.4%) 1. Only 2.8% is eliminated via the bile owing to scopolamine butylbromide's poor absorption.

Half-life

The half life of elimination is 1-5 hours 1.

Clearance

Total clearace is 1.2 liters per minute 1.

Adverse Effects
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
AclidiniumThe risk or severity of adverse effects can be increased when Butylscopolamine is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Butylscopolamine.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Butylscopolamine.
AlimemazineAlimemazine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Butylscopolamine.
AlmotriptanAlmotriptan may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
AlosetronAlosetron may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Butylscopolamine bromide0GH9JX37C8149-64-4HOZOZZFCZRXYEK-GSWUYBTGSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BuscopanSolutionIntramuscular; Intravenous; SubcutaneousSanofi Aventis1976-12-31Not applicableCanada
BuscopanTabletOralSanofi Aventis1976-12-31Not applicableCanada
Buscopan Sup 10mgSuppositoryRectalBoehringer Ingelheim (Canada) Ltd Ltee1976-12-312001-07-30Canada
Hyoscine Butylbromide Injection Sandoz StandardSolutionIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1997-08-25Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
A03DB04 — Butylscopolamine and analgesicsA03BB01 — Butylscopolamine
Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
2Z3E1OF81V
CAS number
7182-53-8
InChI Key
YBCNXCRZPWQOBR-WVHCHWADSA-N
InChI
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
IUPAC Name
(1R,2R,4S,5S,7R)-9-butyl-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
SMILES
CCCC[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1

References

General References
  1. Tytgat GN: Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain. Drugs. 2007;67(9):1343-57. [PubMed:17547475]
KEGG Drug
D01451
PubChem Compound
6852391
PubChem Substance
310265192
ChemSpider
21782131
RxNav
1085787
ChEBI
145701
ChEMBL
CHEMBL1618102
ZINC
ZINC000100047075
Wikipedia
Butylscopolamine
AHFS Codes
  • 12:08.08 — Antimuscarinics Antispasmodics
FDA label
Download (459 KB)
MSDS
Download (182 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionBradycardia / Cesarean Section Complications / Spinal Anesthetics Causing Adverse Effects in Therapeutic Use1
4CompletedPreventionFamily Planning1
4CompletedPreventionPain Relief With HSG1
4CompletedTreatmentDyspepsia / Emergency / Pain1
4CompletedTreatmentVaginal Delivery1
4RecruitingSupportive CareVaginal Delivery1
4RecruitingTreatmentAbdominal Cramps1
4RecruitingTreatmentLabor Long1
4Unknown StatusDiagnosticColonic Adenomas1
3CompletedPreventionBile Duct Diseases / ERCP / Pancreatic Diseases1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
SuppositoryRectal
SolutionIntramuscular; Intravenous; Subcutaneous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00201 mg/mLALOGPS
logP0.79ALOGPS
logP-1.9ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity109.51 m3·mol-1ChemAxon
Polarizability39.82 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Tytgat GN: Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain. Drugs. 2007;67(9):1343-57. [PubMed:17547475]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Tytgat GN: Hyoscine butylbromide: a review of its use in the treatment of abdominal cramping and pain. Drugs. 2007;67(9):1343-57. [PubMed:17547475]

Drug created on November 10, 2015 13:46 / Updated on August 05, 2020 23:35

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