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

Similar Structures

Synonyms

butilescopolamina
N-butylscopolammonium
N-butylscopolammonium cation
N-butylscopolammonium ion

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Butylscopolamine bromide	0GH9JX37C8	149-64-4	HOZOZZFCZRXYEK-GSWUYBTGSA-M

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Buscopan	Tablet	10 mg	Oral	Sanofi Aventis	1976-12-31	Not applicable
Buscopan	Liquid	20 mg	Intramuscular; Intravenous; Subcutaneous	Sanofi Aventis	1976-12-31	Not applicable
Buscopan Sup 10mg	Suppository	10 mg	Rectal	Boehringer Ingelheim (Canada) Ltd Ltee	1976-12-31	2001-07-30
Hyoscine Butylbromide Injection Sandoz Standard	Solution	20 mg	Intramuscular; Intravenous; Subcutaneous	Sandoz Canada Incorporated	1997-08-25	Not applicable

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

Smooth muscle relaxation prior to radiological procedures

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	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

Drug	Interaction
1,10-Phenanthroline	The therapeutic efficacy of Butylscopolamine can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of Tachycardia can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Butylscopolamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of Tachycardia can be increased when Butylscopolamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of Tachycardia can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Butylscopolamine.
4-Methoxyamphetamine	4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
7-Nitroindazole	7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
Abediterol	The risk or severity of Tachycardia can be increased when Butylscopolamine is combined with Abediterol.
Acepromazine	Acepromazine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
Aceprometazine	Aceprometazine may increase the central nervous system depressant (CNS depressant) activities of Butylscopolamine.
Acetaminophen	The risk or severity of adverse effects can be increased when Butylscopolamine is combined with Acetaminophen.

Food Interactions

Not Available

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
ChEBI: 32123
ChEMBL: CHEMBL1618102
Wikipedia: Butylscopolamine

ATC Codes

A03DB04 — Butylscopolamine and analgesics

A03BB01 — 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
1	Completed	Treatment	Healthy Volunteers	3
1	Completed	Treatment	Renal Colic	1
2	Completed	Treatment	Colic	1
2	Completed	Treatment	Gastrointestinal Diseases	1
2, 3	Completed	Prevention	Endoscopy	1
3	Completed	Prevention	Bile Duct Diseases / ERCP / Pancreatic Diseases	1
3	Completed	Treatment	Intestinal Diseases	1
3	Recruiting	Treatment	Acute Abdomen / Children	1
3	Recruiting	Treatment	Prolonged Labour	1
4	Completed	Prevention	Family Planning	1
4	Completed	Prevention	Pain Relief With HSG	1
4	Completed	Treatment	Emergency / Indigestion / Pain NOS	1
4	Completed	Treatment	Vaginal Delivery	1
4	Recruiting	Supportive Care	Vaginal Delivery	1
4	Recruiting	Treatment	Abdominal Cramps	1
Not Available	Completed	Diagnostic	Hysteroscopic Surgery / Postoperative pain	1
Not Available	Not Yet Recruiting	Treatment	Labour	1
Not Available	Not Yet Recruiting	Treatment	Prolonged Labour	1
Not Available	Recruiting	Diagnostic	Constipation - Functional / Irritable Bowel Syndrome Characterized by Constipation	1
Not Available	Recruiting	Diagnostic	Gastrointestinal Imaging With pCLE	1
Not Available	Unknown Status	Treatment	Infertilities	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Liquid	Intramuscular; Intravenous; Subcutaneous	20 mg
Tablet	Oral	10 mg
Suppository	Rectal	10 mg
Solution	Intramuscular; Intravenous; Subcutaneous	20 mg

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

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

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

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 April 18, 2019 06:15

Butylscopolamine

Identification

Structure for Butylscopolamine (DB09300)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References