Butylscopolamine

Identification

Summary

Butylscopolamine is an antispasmodic and anticholinergic agent used for the symptomatic treatment of abdominal cramping and pain.

Brand Names
Buscopan
Generic Name
Butylscopolamine
DrugBank Accession Number
DB09300
Background

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGastrointestinal spastic and hypermotility disorders•••••••••••••••••
Treatment ofInfantile hypertrophic pyloric stenosis•••••••••••••••••
Used in combination to treatMenstrual crampsCombination Product in combination with: Ibuprofen (DB01050), Caffeine (DB00201)••• •••••••••• ••••••
Treatment ofMenstrual cramps•••••••••••••••••
Used in combination to treatMuscle spasmsCombination Product in combination with: Metamizole (DB04817)•••••••••••••••••••••• ••••••••• ••••••• ••••••• ••••••• •••• ••••••• ••••••• ••••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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

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
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.
AlfentanilThe risk or severity of adverse effects can be increased when Butylscopolamine is combined with Alfentanil.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Butylscopolamine.
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Butylscopolamine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Butylscopolamine bromide0GH9JX37C8149-64-4HOZOZZFCZRXYEK-GSWUYBTGSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BuscopanSolution20 mg / mLIntramuscular; Intravenous; SubcutaneousSanofi Consumer Health Inc1976-12-31Not applicableCanada flag
BuscopanTablet10 mgOralSanofi Consumer Health Inc / Sanofi Sante Grand Public Inc1976-12-31Not applicableCanada flag
Buscopan Sup 10mgSuppository10 mg / supRectalBoehringer Ingelheim (Canada) Ltd Ltee1976-12-312001-07-30Canada flag
Hyoscine Butylbromide InjectionSolution20 mg / mLIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1997-08-25Not applicableCanada flag
Hyoscine Butylbromide Injection BPSolution20 mg / mLIntramuscular; Intravenous; SubcutaneousOmega Laboratories LtdNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-hyoscineTablet10 mgOralAccel Pharma Inc2021-08-19Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BUSCOPAN TABLET 10 mgTablet, sugar coated10 mgOralOPELLA HEALTHCARE SINGAPORE PTE. LTD.1989-04-07Not applicableSingapore flag
COLOSPAN TABLET B.P. 10 mgTablet, sugar coated10.00 mgOralGOLDPLUS UNIVERSAL PTE LTD1993-05-24Not applicableSingapore flag
DHACOPAN SYRUP 5 mg/5 mlSyrup5 mgOralTEVA PHARMACEUTICAL INVESTMENTS SINGAPORE PTE. LTD.1989-05-31Not applicableSingapore flag
DHACOPAN TABLET 10 mgTablet, film coated10 mgOralTEVA PHARMACEUTICAL INVESTMENTS SINGAPORE PTE. LTD.1989-04-22Not applicableSingapore flag
FUCON CAPSULE 10 mgCapsule10 mgOralYUNG SHIN PHARMACEUTICAL (SINGAPORE) PTE LTD1992-09-10Not applicableSingapore flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACETAMINOFEN 325 MG + BUTIL BROMURO DE HIOSCINA 10 MG TABLETASButylscopolamine bromide (10 mg) + Acetaminophen (325 mg)TabletOralCOASPHARMA S.A.S. PLANTA PALOQUEMAO2007-02-01Not applicableColombia flag
ACETAMINOFÉN 325 MG + N-BUTILBROMURO DE HIOSCINA 10 MGButylscopolamine bromide (10 mg) + Acetaminophen (325 mg)TabletOralCOASPHARMA S.A.S.2021-06-10Not applicableColombia flag
ACETAMINOFEN 325 MG + N-BUTILBROMURO DE HIOSCINA 10MG TABLETASButylscopolamine bromide (10 mg) + Acetaminophen (325 mg)TabletOralCOLOMPACK S.A.2008-09-25Not applicableColombia flag
ADIFAR TABLETAButylscopolamine bromide (10 mg) + Acetaminophen (325 mg)TabletOralCOASPHARMA S.A.S.2007-08-152022-12-28Colombia flag
ADIPINA TABLETASButylscopolamine bromide (10 mg) + Acetaminophen (325 mg)TabletOralCOASPHARMA S.A.S. PLANTA PALOQUEMAO2007-02-082023-11-07Colombia flag

Categories

ATC Codes
A03DB04 — Butylscopolamine and analgesicsA03BB01 — Butylscopolamine
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

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. [Article]
  2. Duo-Pas Product Information [Link]
KEGG Drug
D01451
PubChem Compound
6852391
PubChem Substance
310265192
ChemSpider
21782131
RxNav
1085787
ChEBI
145701
ChEMBL
CHEMBL1618102
ZINC
ZINC000100047075
Wikipedia
Hyoscine_butylbromide
FDA label
Download (459 KB)
MSDS
Download (182 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionBradycardia / Complications; Cesarean Section / Spinal Anesthetics Causing Adverse Effects in Therapeutic Use1
4CompletedPreventionFamily Planning1
4CompletedPreventionPain Relief With HSG1
4CompletedPreventionVomiting1
4CompletedSupportive CareVaginal Delivery1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral10.000 mg
SolutionParenteral
SolutionIntravenous20.000 mg
Capsule, liquid filledOral10 mg
Injection, solutionParenteral20 mg/ml
SolutionIntramuscular; Intravenous
TabletOral20 mg
SolutionIntravenous
Injection, solutionIntramuscular; Intravenous20 MG/ML
SuppositoryRectal
SuppositoryRectal10 MG
Tablet, coatedOral
Tablet, sugar coatedOral10 mg/1
Injection, solution
Injection, solution20 mg/ml
SuppositoryRectal
Tablet, coatedOral500 MG
SuppositoryRectal10 mg / sup
Injection, solutionIntravenous
SolutionParenteral20 mg
SolutionIntramuscular; Intravenous; Subcutaneous
Tablet, sugar coatedOral10.00 mg
InjectionIntramuscular; Intravenous20 mg/ml
InjectionParenteral
SyrupOral5 mg
Tablet, delayed releaseOral
Tablet, coatedOral
Capsule, coatedOral
SolutionIntramuscular
Capsule, liquid filledOral
SolutionOral6.670 mg
CapsuleOral
SolutionOral6.67 mg
SolutionOral10 mg
CapsuleOral
CapsuleOral10 mg
InjectionIntramuscular; Intravenous; Subcutaneous20 mg/ml
Injection, solutionIntramuscular; Intravenous; Subcutaneous
SyrupOral
InjectionIntramuscular; Intravenous
Tablet, film coatedOral
SolutionIntramuscular; Intravenous20 mg
SolutionOral
TabletOral10.00 mg
Injection
SolutionIntramuscular; Intravenous; Subcutaneous20 mg / mL
Tablet, sugar coatedOral
Injection, solutionIntravenous20 MG/ML
TabletOral10.000 mg
InjectionIntramuscular; Intravenous; Subcutaneous
SolutionParenteral20.000 mg
Injection, solutionIntramuscular; Intravenous
SolutionIntramuscular; Intravenous2000000 mg
SolutionIntramuscular; Intravenous; Subcutaneous20 mg
SolutionIntramuscular20 mg
SolutionIntramuscular20.000 mg
Tablet, film coatedOral
TabletOral
Injection, solutionIntramuscular; Intravenous; Subcutaneous20 mg/ml
Tablet, coatedOral10 mg
SuppositoryRectal7.5 mg
TabletOral
Tablet, sugar coatedOral
Solution20 mg/1ml
Tablet, delayed releaseOral10 mg
SyrupOral5 mg/5ml
TabletOral10 mg
Tablet, film coatedOral10 mg
Elixir5 mg/5ml
Tablet, sugar coatedOral10 mg
Solution5 mg/5ml
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
SpectrumSpectrum TypeSplash Key
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.87761
predicted
DeepCCS 1.0 (2019)
[M+H]+180.7025
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.30832
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
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. [Article]

Drug created at November 10, 2015 20:46 / Updated at March 29, 2024 03:23