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Details

Stereochemistry ACHIRAL
Molecular Formula C21H26NO3
Molecular Weight 340.436
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of METHANTHELINE

SMILES

CC[N+](C)(CC)CCOC(=O)C1C2=C(OC3=C1C=CC=C3)C=CC=C2

InChI

InChIKey=GZHFODJQISUKAY-UHFFFAOYSA-N
InChI=1S/C21H26NO3/c1-4-22(3,5-2)14-15-24-21(23)20-16-10-6-8-12-18(16)25-19-13-9-7-11-17(19)20/h6-13,20H,4-5,14-15H2,1-3H3/q+1

HIDE SMILES / InChI

Molecular Formula C21H26NO3
Molecular Weight 340.436
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Methantheline is a synthetic quarternary ammonium antimuscarinic used to relieve cramps or spasms of the stomach, intestines, and bladder. It is indicated for the treatment of peptic ulcer disease, irritable bowel syndrome, pancreatitis, gastritis, biliary dyskinesia, pylorosplasm, and reflex neurogenic bladder in children. It can be used together with antacids or other medicines, such as H2-receptor antagonists, in the treatment of peptic ulcer. Methantheline bromide (diethyl-methyl [2-(9 xanthenyl carbonyloxy) ethyl] ammonium bromide) is marketed to treat neurogenic bladder instability. In comparison with atropine, it influences the parasympathetic nervous transmission more by ganglionic rather than peripheral muscarinic receptor blockade. Methantheline 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. Clinical effects after single therapeutic doses of 50-100 mg last for about 6 hours which is longer than after atropine. The drug relaxes smooth muscles of the gastrointestinal and urogenital tract. Furthermore, it inhibits bronchial, salivary and sweat glands secretion, lowers the production of gastric juice and disturbs accommodation. A recent randomised double-blind placebo-controlled study using a new commercial preparation of methantheline bromide (Vagantin, Germany) demonstrated significant sweat reduction and was evaluated as is an effective and safe treatment of axillary hyperhidrosis.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BANTHINE
Primary
BANTHINE
Primary
BANTHINE

Cmax

ValueDoseCo-administeredAnalytePopulation
25 ng/mL
100 mg single, oral
METHANTHELINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
100 mg single, oral
METHANTHELINE plasma
Homo sapiens

Doses

AEs

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Banthine at a dose of 50–100 mg every 4 h in patients with palmar hyperhidrosis
Route of Administration: Oral
In Vitro Use Guide
The effect of methantheline on the reactivation by HI 6 of soman-inhibited human erythrocyte acetylcholinesterase (AChE) was investigated in vitro using purified human erythrocyte AChE or washed human erythrocytes. Methantheline was found to be a mixed competitive/non-competitive inhibitor of AChE at Ki 240 +/- 10 uM.
Substance Class Chemical
Record UNII
36EI79TX7I
Record Status Validated (UNII)
Record Version