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Details

Stereochemistry ACHIRAL
Molecular Formula C17H32NO2.Br
Molecular Weight 362.345
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANISOTROPINE METHYLBROMIDE

SMILES

[Br-].CCCC(CCC)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)[N+]2(C)C

InChI

InChIKey=QSFKGMJOKUZAJM-CNKDKAJDSA-M
InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1/t14-,15+,16+;

HIDE SMILES / InChI

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

Molecular Formula C17H32NO2
Molecular Weight 282.4415
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Methyl anisotropinium (Anisotropine methylbromide) is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion. Methyl anisotropinium inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands. It is used in conjunction with antacids or histamine H2-receptor antagonists in the treatment of peptic ulcer, to reduce further gastric acid secretion and delay gastric emptying.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Valpin

Doses

AEs

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Oral route a) As an adjunct in the treatment of PEPTIC ULCER DISEASE, the recommended oral dose of anisotropine methylbromide is 50 milligrams 3 times daily; the dose should be adjusted according to therapeutic response (Prod Info Valpin 50(R), 1993). b) In the treatment of VISCERAL SPASMS the oral dose of anisotropine methylbromide is 10 milligrams 3 to 4 times daily
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
62M960DHIL
Record Status Validated (UNII)
Record Version