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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30NO4.Br
Molecular Weight 440.371
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYLSCOPOLAMINE BROMIDE

SMILES

[Br-].[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2[N@@+]3(C)CCCC)OC(=O)[C@H](CO)C4=CC=CC=C4

InChI

InChIKey=HOZOZZFCZRXYEK-GSWUYBTGSA-M
InChI=1S/C21H30NO4.BrH/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;1H/q+1;/p-1/t15-,16-,17-,18+,19-,20+,22?;/m1./s1

HIDE SMILES / InChI

Molecular Formula C21H29NO4
Molecular Weight 359.4593
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Butylscopolamine (trade name Buscopan) is a peripherally acting antimuscarinic, anticholinergic agent. It is a natural substance extracted from Duboisia plant species as Scopolamine (hyoscine) and chemically modified to the quaternary ammonium compound hyoscine butylbromide. It was first registered in Germany in 1951 and marketed in 1952, and is available worldwide both as a prescription drug and as an over-the-counter medicine in many countries. Buscopan is used to treat spasm of the gastrointestinal tract, biliary spasm, renal spasm, diagnostic aid in radiology. In the United States Buscopan approved by FDA to be used in the veterinary medicine only - for the control of abdominal pain associated with spasmodic colic, flatulent colic, and simple impactions in horses. Butylbromide has a high affinity for muscarinic receptors located on the smooth-muscle cells of the GI tract. Its anticholinergic action exerts a smooth-muscle relaxing/spasmolytic effect. Blockade of the muscarinic receptors in the GI tract is the basis for its use in the treatment of abdominal pain secondary to cramping. Hyoscine butylbromide also binds to nicotinic receptors, which induces a ganglion-blocking effect.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BUSCOPAN
Palliative
BUSCOPAN

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
For adults and children over 6 years: 2 Buscopan tablets ( 10 mg each) four times daily or 1x20 mg Buscopan Forte tablet four times daily. Buscopan tablets are not recommended for children under 6 years of age. 1 or 2 ampules (20 or 40 mg) by intramuscular or slow intravenous injection. A maximum daily dose of 100 mg should not be exceeded. BUSCOPAN tablets and ampules should not be taken on a continuous daily basis or for extended periods without investigating the cause of abdominal pain.
Route of Administration: Other
In Vitro Use Guide
Hyoscine butylbromide at the concentration range 1 nmol/L-10 umol/L effects on muscle activity were studied with isometric force transducers and calcium imaging and it effects on epithelial secretion were studied with with Ussing chamber technique and on enteric neurons using fast neuroimaging. Hyoscine butylbromide concentration dependently reduced muscle contractions, calcium mobilization, and epithelial secretion induced by the muscarinic agonist bethanechol with IC50 values of 429, 121, and 224 nmol/L, respectively.
Substance Class Chemical
Record UNII
0GH9JX37C8
Record Status Validated (UNII)
Record Version