anisotropine methylbromide

Trade name: valpin

Small moleculeapproved

Approved

Nov 23, 1962

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 Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents.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. — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 2 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Timeline

1960s

Nov 23, 1962
Endo Pharmaceuticals — Earliest FDA Approval
Nov 23, 1962
Endo Pharmaceuticals — NDA Secondary Org
Nov 23, 1962
Endo Pharmaceuticals — NDA Organization

1980s

Apr 14, 1983
Watson Pharmaceuticals — Marketing Organization

Indications

Approved for

Mechanism of action

Muscarinic acetylcholine receptor M1ANTAGONIST
CHRM1 antagonist
Role in regulating gastric secretion, M1 likely involved
- Muscarinic acetylcholine receptor M1 (CHRM1) ↗
Muscarinic acetylcholine receptor M3ANTAGONIST
CHRM3 antagonist
Role in regulating gastric secretion, M3 likely involved
- Muscarinic acetylcholine receptor M3 (CHRM3) ↗

Approval history

approvedNov 23, 1962

Chemistry & pharmacology

Loading structure…

SMILES

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

Mol. weight: 282.45 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Single Stereoisomer
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Discontinued

Oral

Yes

Parenteral

Topical

Sources

Also known as

8-methyl-3-(2-propylpentanoyloxy)tropinium bromide
8-methyl-3-(2-propylpentanoyloxy)tropinium bromide
8-methyltropinium bromide 2-propylpentanoate
8-methyltropinium bromide 2-propylpentanoate
8-methyltropinium bromide 2-propylvalerate
8-methyltropinium bromide 2-propylvalerate
anisotropine
anisotropine
anisotropine
anisotropine
anisotropine methobromide
anisotropine methobromide
anisotropine methobromide
anisotropine methylbromide
anisotropine methylbromide
anisotropine methylbromide
anisotropine methylbromide
anisotropine methylbromide
anisotropine methylbromide
anisotropine methylbromide
anisotropine methyl bromide
anisotropine methylbromide, (endo)-isomer
endo-8,8-dimethyl-3-((1-oxo-2-propylpentyl)oxy)-8-azoniabicyclo(3.2.1)octane bromide
endo-8,8-dimethyl-3-((1-oxo-2-propylpentyl)oxy)-8-azoniabicyclo(3.2.1)octane bromide
methylbromure d'octatropine
methylbromure d'octatropine
methyloctatropine bromide
metilbromuro de octatropina
metilbromuro de octatropina
octatropine
octatropine methylbromide
octatropine methylbromide
octatropine methylbromide
octatropine methylbromide
octatropine methylbromide
octatropini methylbromidum
octatropini methylbromidum
octatropone bromide
octatropone bromide
octotropine methylbromide
valpin
valpin
valpin
valpin
valpin
valpin 50
valpin 50

Organizations

Marketing (3)

Organization	Org type	Relationship	Date
Endo Pharmaceuticals	For profit	NDA2	Nov 23, 1962
Endo Pharmaceuticals	For profit	NDA	Nov 23, 1962
Watson Pharmaceuticals	For profit	MKTG	Apr 14, 1983