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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
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.
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
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
Learn about our commercial Adverse Effects data.
Learn More- 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.
Drug Interaction Unlock Additional DataAcetazolamide 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 Alfentanil is combined with Butylscopolamine. 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. Alosetron Alosetron may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- 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 Unlock Additional DataBuscopan Solution Intramuscular; Intravenous; Subcutaneous Sanofi Aventis 1976-12-31 Not applicable Canada 
Buscopan Tablet Oral Sanofi Aventis 1976-12-31 Not applicable Canada Buscopan Sup 10mg Suppository Rectal Boehringer Ingelheim (Canada) Ltd Ltee 1976-12-31 2001-07-30 Canada Hyoscine Butylbromide Injection Sandoz Standard Solution Intramuscular; Intravenous; Subcutaneous Sandoz Canada Incorporated 1997-08-25 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
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
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
- 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]
- External Links
- KEGG Drug
- D01451
- PubChem Compound
- 6852391
- PubChem Substance
- 310265192
- ChemSpider
- 21782131
- 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
Phase Status Purpose Conditions Count 4 Completed Prevention Bradycardia / Cesarean Section Complications / 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 Supportive Care Vaginal Delivery 1 4 Recruiting Treatment Abdominal Cramps 1 4 Recruiting Treatment Labor Long 1 4 Unknown Status Diagnostic Colonic Adenomas 1 3 Completed Prevention Bile Duct Diseases / ERCP / Pancreatic Diseases 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Suppository Rectal Solution Intramuscular; Intravenous; Subcutaneous - 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
- 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. [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
- 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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