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
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
- Gastrointestinal spastic and hypermotility disorders
- Infantile Hypertrophic Pyloric Stenosis
- Menstrual Distress (Dysmenorrhea)
- Muscle Spasms
- Pain
- Primary Dysmenorrhoea
- Stiffness of the Urinary Tract
- Acute biliary spasm
- Acute gastrointestinal spasms
- Acute genitourinary spasms
- Genitourinary smooth muscle spasm
- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine 1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine. Acetazolamide Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine. Acetophenazine Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine. Aclidinium 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. Agomelatine Agomelatine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine. Alfentanil The risk or severity of adverse effects can be increased when Butylscopolamine is combined with Alfentanil. Alimemazine Alimemazine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Butylscopolamine. Almotriptan Almotriptan may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine. 
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- 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 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 BP Solution 20 mg / mL Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd Not applicable Not applicable Canada Hyoscine Butylbromide Injection Sandoz Standard Solution 20 mg / mL Intramuscular; Intravenous; Subcutaneous Sandoz Canada Incorporated 1997-08-25 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 SANOFI-AVENTIS SINGAPORE PTE. LTD. 1989-07-04 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 DRUG HOUSES OF AUSTRALIA PTE. LTD. 1989-05-31 Not applicable Singapore DHACOPAN TABLET 10 mg Tablet, film coated 10 mg Oral DRUG HOUSES OF AUSTRALIA PTE. LTD. 1989-04-22 Not applicable Singapore FUCON CAPSULE 10 mg Capsule 10 mg Oral YUNG SHIN PHARMACEUTICAL (SINGAPORE) PTE LTD 1992-10-09 Not applicable Singapore HYOMIDE TABLET 10 mg Tablet, sugar coated 10 mg Oral BEACONS PHARMACEUTICALS PTE. LTD. 1989-05-24 Not applicable Singapore HYOSCINE BUTYLBROMIDE TABLET 10 mg Tablet, film coated 10 mg Oral SUNWARD PHARMACEUTICAL PRIVATE LIMITED 1989-07-04 Not applicable Singapore HYOSUN SYRUP 5mg/5 ml Syrup 5 mg/5ml Oral SUNWARD PHARMACEUTICAL PRIVATE LIMITED 1993-05-20 Not applicable Singapore SP-ANSPAZ SYRUP 5 mg/5 ml Syrup 5 mg/5ml Oral SPECTRUM HEALTH PROMOTION PTE LTD 1997-05-20 Not applicable Singapore SP-ANSPAZ TABLET 10 mg Tablet, film coated 10 mg Oral SPECTRUM HEALTH PROMOTION PTE LTD 1997-07-31 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 Not applicable Colombia ADIPINA TABLETAS Butylscopolamine bromide (10 mg) + Acetaminophen (325 mg) Tablet Oral COASPHARMA S.A.S. PLANTA PALOQUEMAO 2007-02-08 Not applicable Colombia ASPASMIL® COMPOSITUM TABLETAS Butylscopolamine bromide (10 mg) + Acetaminophen (325 mg) Tablet Oral COASPHARMA S.A.S. 2018-08-15 Not applicable Colombia BUSCAPINA FEM Butylscopolamine (20 mg) + Ibuprofen (400 mg) Tablet Oral PHARMETIQUE S.A 2007-02-01 Not applicable Colombia BUSCOPAN PLUS FILM TABLET, 20 ADET Butylscopolamine bromide (10 mg) + Acetaminophen (500 mg) Tablet, film coated Oral SANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ. 2020-08-14 Not applicable Turkey 
BUSCOPAN PLUS FILM TABLET, 30 ADET Butylscopolamine bromide (10 mg) + Acetaminophen (500 mg) Tablet, film coated Oral SANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ. 2020-08-14 Not applicable Turkey BUSCOPAN PLUS FILM TABLET, 50 ADET Butylscopolamine bromide (10 mg) + Acetaminophen (500 mg) Tablet, film coated Oral SANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ. 2020-08-14 Not applicable Turkey
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
- Ammonium Compounds
- 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
- Nitrogen Compounds
- Onium Compounds
- 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
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 Treatment Dyspepsia / Emergency / Pain 1 4 Completed Treatment Vaginal Delivery 1 4 Recruiting Prevention Vomiting 1 4 Recruiting Supportive Care Vaginal Delivery 1 4 Recruiting Treatment Labor Long 1 4 Unknown Status Diagnostic Colonic Adenomas 1 4 Unknown Status Treatment Abdominal Cramping 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intramuscular; Intravenous 20 MG/ML Capsule, liquid filled Oral 10 mg Injection, solution Parenteral Solution Intramuscular; Intravenous Suppository Rectal 10 MG Tablet, sugar coated Oral 10 mg/1 Tablet, sugar coated Oral Suppository Rectal Injection, solution Suppository Rectal Tablet, coated Oral Tablet, coated Oral 500 MG Tablet, film coated Oral Suppository Rectal 10 mg / sup Solution Intramuscular; Intravenous; Subcutaneous 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 Solution Parenteral Tablet, delayed release Oral Capsule, coated Oral 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 Solution Oral Injection Solution Intramuscular; Intravenous; Subcutaneous 20 mg / mL Injection, solution Intravenous Tablet, coated Oral Injection Intramuscular; Intravenous; Subcutaneous Injection, solution Intramuscular; Intravenous Capsule, liquid filled Oral Solution Intramuscular; Intravenous 20 mg Solution Parenteral 20 mg Solution Intramuscular 20 mg Tablet, film coated Oral Tablet Oral Tablet, coated Oral 10 mg Suppository Rectal 7.5 mg Tablet Oral Tablet, sugar coated Oral Solution Intravenous 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
- Not Available
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 on November 10, 2015 20:46 / Updated on October 18, 2021 04:55