Butylscopolamine

Targets (2)Biointeractions (2)

Identification

Name
Butylscopolamine
Accession Number
DB09300  (DB11535)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
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.

Structure
Thumb
Similar Structures
Synonyms
  • butilescopolamina
  • N-butylscopolammonium
  • N-butylscopolammonium cation
  • N-butylscopolammonium ion
Product Ingredients
IngredientUNIICASInChI Key
Butylscopolamine bromide0GH9JX37C8149-64-4HOZOZZFCZRXYEK-GSWUYBTGSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BuscopanLiquid20 mgIntramuscular; Intravenous; SubcutaneousSanofi Aventis1976-12-31Not applicableCanada
BuscopanTablet10 mgOralSanofi Aventis1976-12-31Not applicableCanada
Buscopan Sup 10mgSuppository10 mgRectalBoehringer Ingelheim (Canada) Ltd Ltee1976-12-312001-07-30Canada
Hyoscine Butylbromide Injection Sandoz StandardSolution20 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1997-08-25Not applicableCanada
Categories
UNII
2Z3E1OF81V
CAS number
7182-53-8
Weight
Average: 360.473
Monoisotopic: 360.21693487
Chemical Formula
C21H30NO4
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

Pharmacology

Indication

Used to treat abdmoninal cramping and pain [Label].

Associated Conditions
Associated Therapies
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.

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].

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

Interactions

Drug Interactions
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Butylscopolamine can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of Tachycardia can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Butylscopolamine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
7-Nitroindazole7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
AbediterolThe risk or severity of Tachycardia can be increased when Butylscopolamine is combined with Abediterol.
AcebutololThe risk or severity of Tachycardia can be increased when Acebutolol is combined with Butylscopolamine.
Food Interactions
Not Available

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]
External Links
KEGG Drug
D01451
PubChem Compound
6852391
PubChem Substance
310265192
ChemSpider
21782131
ChEBI
32123
ChEMBL
CHEMBL1618102
Wikipedia
Butylscopolamine
ATC Codes
A03DB04 — Butylscopolamine and analgesicsA03BB01 — Butylscopolamine
AHFS Codes
  • 12:08.08 — Antimuscarinics Antispasmodics
FDA label
Download (459 KB)
MSDS
Download (182 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentRenal Colic1
2CompletedTreatmentColic1
2CompletedTreatmentGastrointestinal Diseases1
2, 3CompletedPreventionEndoscopy1
3CompletedPreventionBile Duct Diseases / ERCP / Pancreatic Diseases1
3CompletedTreatmentIntestinal Diseases1
3RecruitingTreatmentAcute Abdomen / Children1
3RecruitingTreatmentProlonged Labour1
4CompletedPreventionFamily Planning1
4CompletedPreventionPain Relief With HSG1
4CompletedTreatmentEmergency / Indigestion / Pain NOS1
4CompletedTreatmentVaginal Delivery1
4RecruitingSupportive CareVaginal Delivery1
4RecruitingTreatmentAbdominal Cramps1
Not AvailableCompletedDiagnosticHysteroscopic Surgery / Postoperative pain1
Not AvailableNot Yet RecruitingTreatmentLabour1
Not AvailableNot Yet RecruitingTreatmentProlonged Labour1
Not AvailableRecruitingDiagnosticConstipation - Functional / Irritable Bowel Syndrome Characterized by Constipation1
Not AvailableRecruitingDiagnosticGastrointestinal Imaging With pCLE1
Not AvailableUnknown StatusTreatmentInfertilities1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidIntramuscular; Intravenous; Subcutaneous20 mg
TabletOral10 mg
SuppositoryRectal10 mg
SolutionIntramuscular; Intravenous; Subcutaneous20 mg
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

Taxonomy

Classification
Not classified

Targets

Details1. Muscarinic acetylcholine receptor M3
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]
Details2. Muscarinic acetylcholine receptor M2
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 January 20, 2019 03:32