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
Structure for Butylscopolamine (DB09300)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Gastrointestinal spastic and hypermotility disorders •••••••••••• ••••• Treatment of Infantile hypertrophic pyloric stenosis •••••••••••• ••••• Used in combination to treat Menstrual cramps Combination Product in combination with: Ibuprofen (DB01050), Caffeine (DB00201) ••• ••• ••••••• •••••• Treatment of Menstrual cramps •••••••••••• ••••• Used in combination to treat Muscle spasms Combination Product in combination with: Metamizole (DB04817) •••••••••••• •••••••••• ••••••••• ••••••• ••••••• ••••••• •••• ••••••• ••••••• ••••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AMuscarinic acetylcholine receptor M3 antagonistHumans UMuscarinic acetylcholine receptor M2 antagonistHumans - 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.
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- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAclidinium The risk or severity of adverse effects can be increased when Butylscopolamine is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Butylscopolamine. Alfentanil The risk or severity of adverse effects can be increased when Butylscopolamine is combined with Alfentanil. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Butylscopolamine. Amantadine The risk or severity of adverse effects can be increased when Amantadine is combined with Butylscopolamine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Butylscopolamine bromide 0GH9JX37C8 149-64-4 HOZOZZFCZRXYEK-GSWUYBTGSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Buscopan Solution 20 mg / mL Intramuscular; Intravenous; Subcutaneous Sanofi Consumer Health Inc 1976-12-31 Not applicable Canada 
Buscopan Tablet 10 mg Oral Sanofi Consumer Health Inc / Sanofi Sante Grand Public Inc 1976-12-31 Not applicable Canada Buscopan Sup 10mg Suppository 10 mg / sup Rectal Boehringer Ingelheim (Canada) Ltd Ltee 1976-12-31 2001-07-30 Canada Hyoscine Butylbromide Injection Solution 20 mg / mL Intramuscular; Intravenous; Subcutaneous Sandoz Canada Incorporated 1997-08-25 Not applicable Canada Hyoscine Butylbromide Injection BP Solution 20 mg / mL Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Accel-hyoscine Tablet 10 mg Oral Accel Pharma Inc 2021-08-19 Not applicable Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image BUSCOPAN TABLET 10 mg Tablet, sugar coated 10 mg Oral OPELLA HEALTHCARE SINGAPORE PTE. LTD. 1989-04-07 Not applicable Singapore 
COLOSPAN TABLET B.P. 10 mg Tablet, sugar coated 10.00 mg Oral GOLDPLUS UNIVERSAL PTE LTD 1993-05-24 Not applicable Singapore DHACOPAN SYRUP 5 mg/5 ml Syrup 5 mg Oral TEVA PHARMACEUTICAL INVESTMENTS SINGAPORE PTE. LTD. 1989-05-31 Not applicable Singapore DHACOPAN TABLET 10 mg Tablet, film coated 10 mg Oral TEVA PHARMACEUTICAL INVESTMENTS SINGAPORE PTE. LTD. 1989-04-22 Not applicable Singapore FUCON CAPSULE 10 mg Capsule 10 mg Oral YUNG SHIN PHARMACEUTICAL (SINGAPORE) PTE LTD 1992-09-10 Not applicable Singapore - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACETAMINOFEN 325 MG + BUTIL BROMURO DE HIOSCINA 10 MG TABLETAS Butylscopolamine bromide (10 mg) + Acetaminophen (325 mg) Tablet Oral COASPHARMA S.A.S. PLANTA PALOQUEMAO 2007-02-01 Not applicable Colombia 
ACETAMINOFÉN 325 MG + N-BUTILBROMURO DE HIOSCINA 10 MG Butylscopolamine bromide (10 mg) + Acetaminophen (325 mg) Tablet Oral COASPHARMA S.A.S. 2021-06-10 Not applicable Colombia ACETAMINOFEN 325 MG + N-BUTILBROMURO DE HIOSCINA 10MG TABLETAS Butylscopolamine bromide (10 mg) + Acetaminophen (325 mg) Tablet Oral COLOMPACK S.A. 2008-09-25 Not applicable Colombia ADIFAR TABLETA Butylscopolamine bromide (10 mg) + Acetaminophen (325 mg) Tablet Oral COASPHARMA S.A.S. 2007-08-15 2022-12-28 Colombia ADIPINA TABLETAS Butylscopolamine bromide (10 mg) + Acetaminophen (325 mg) Tablet Oral COASPHARMA S.A.S. PLANTA PALOQUEMAO 2007-02-08 2023-11-07 Colombia
Categories
- ATC Codes
- A03DB04 — Butylscopolamine and analgesics
- A03DB — Belladonna and derivatives in combination with analgesics
- A03D — ANTISPASMODICS IN COMBINATION WITH ANALGESICS
- A03 — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Agents producing tachycardia
- Alimentary Tract and Metabolism
- Alkaloids
- Amines
- Anticholinergic Agents
- Antimuscarinics Antispasmodics
- Autonomic Agents
- Aza Compounds
- Azabicyclo Compounds
- Belladonna Alkaloids, Semisynthetic, Quaternary Ammonium Compounds
- Belladonna and Derivatives, Plain
- Cholinergic Agents
- Drugs for Functional Gastrointestinal Disorders
- Muscarinic Antagonists
- Neurotransmitter Agents
- Parasympatholytics
- Peripheral Nervous System Agents
- Quaternary Ammonium Compounds
- Scopolamine Derivatives
- Tropanes
- 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
- External Links
- KEGG Drug
- D01451
- PubChem Compound
- 6852391
- PubChem Substance
- 310265192
- ChemSpider
- 21782131
- 1085787
- ChEBI
- 145701
- ChEMBL
- CHEMBL1618102
- ZINC
- ZINC000100047075
- Wikipedia
- Hyoscine_butylbromide
- FDA label
- Download (459 KB)
- MSDS
- Download (182 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Bradycardia / Complications; Cesarean Section / Spinal Anesthetics Causing Adverse Effects in Therapeutic Use 1 4 Completed Prevention Family Planning 1 4 Completed Prevention Pain Relief With HSG 1 4 Completed Prevention Vomiting 1 4 Completed Supportive Care Vaginal Delivery 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral 10.000 mg Solution Parenteral Solution Intravenous 20.000 mg Capsule, liquid filled Oral 10 mg Injection, solution Parenteral 20 mg/ml Solution Intramuscular; Intravenous Solution Intravenous Injection, solution Intramuscular; Intravenous 20 MG/ML Suppository Rectal Suppository Rectal 10 MG Tablet, coated Oral Tablet, sugar coated Oral 10 mg/1 Injection, solution Injection, solution 20 mg/ml Suppository Rectal Tablet, coated Oral 500 MG Suppository Rectal 10 mg / sup Injection, solution Intravenous Solution Parenteral 20 mg Solution Intramuscular; Intravenous; Subcutaneous Tablet, sugar coated Oral 10.00 mg Injection Intramuscular; Intravenous 20 mg/ml Injection Parenteral Syrup Oral 5 mg Tablet, delayed release Oral Tablet, coated Oral Capsule, coated Oral Solution Intramuscular Capsule, liquid filled Oral Solution Oral 6.670 mg Capsule Oral Solution Oral 6.67 mg Solution Oral 10 mg Capsule Oral Capsule Oral 10 mg Injection Intramuscular; Intravenous; Subcutaneous 20 mg/ml Injection, solution Intramuscular; Intravenous; Subcutaneous Syrup Oral Injection Intramuscular; Intravenous Tablet, film coated Oral Solution Intramuscular; Intravenous 20 mg Solution Oral Tablet Oral 10.00 mg Injection Solution Intramuscular; Intravenous; Subcutaneous 20 mg / mL Tablet, sugar coated Oral Injection, solution Intravenous 20 MG/ML Tablet Oral 10.000 mg Injection Intramuscular; Intravenous; Subcutaneous Solution Parenteral 20.000 mg Injection, solution Intramuscular; Intravenous Solution Intramuscular; Intravenous 2000000 mg Solution Intramuscular; Intravenous; Subcutaneous 20 mg Solution Intramuscular 20 mg Solution Intramuscular 20.000 mg Tablet, film coated Oral Tablet Oral Injection, solution Intramuscular; Intravenous; Subcutaneous 20 mg/ml Tablet, coated Oral 10 mg Suppository Rectal 7.5 mg Tablet Oral Tablet, sugar coated Oral Solution 20 mg/1ml Tablet, delayed release Oral 10 mg Syrup Oral 5 mg/5ml Tablet Oral 10 mg Tablet, film coated Oral 10 mg Elixir 5 mg/5ml Tablet, sugar coated Oral 10 mg Solution 5 mg/5ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00201 mg/mL ALOGPS logP 0.79 ALOGPS logP -1.9 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 15.15 Chemaxon pKa (Strongest Basic) -2.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 59.06 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 109.51 m3·mol-1 Chemaxon Polarizability 39.82 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 178.87761 predictedDeepCCS 1.0 (2019) [M+H]+ 180.7025 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.30832 predictedDeepCCS 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
- 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
- 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 February 20, 2024 23:54