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
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
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 |
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
Doses
AEs
Sourcing
PubMed
Patents
Sample Use Guides
Banthine at a dose of 50–100 mg every 4 h in patients with palmar hyperhidrosis
Route of Administration:
Oral
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.