Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H26NO3.Br |
| Molecular Weight | 420.34 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Br-].CC[N+](C)(CC)CCOC(=O)C1C2=CC=CC=C2OC3=CC=CC=C13
InChI
InChIKey=PQMWYJDJHJQZDE-UHFFFAOYSA-M
InChI=1S/C21H26NO3.BrH/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;1H/q+1;/p-1
| Molecular Formula | C21H26NO3 |
| Molecular Weight | 340.436 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | BrH |
| Molecular Weight | 80.912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P25021 Gene ID: 3274.0 Gene Symbol: HRH2 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BANTHINE Approved UseUnknown Launch Date1951 |
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| Primary | BANTHINE Approved UseUnknown Launch Date1951 |
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| Primary | BANTHINE Approved UseUnknown Launch Date1951 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
25 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22527350/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHANTHELINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22527350/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHANTHELINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
50 mg 4 times / day steady, oral Highest studied dose Dose: 50 mg, 4 times / day Route: oral Route: steady Dose: 50 mg, 4 times / day Sources: |
unhealthy, 46.6 years (range: 25 - 65 years) Health Status: unhealthy Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Sources: |
Other AEs: Dry mouth, Headache... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Dry mouth | 50 mg 4 times / day steady, oral Highest studied dose Dose: 50 mg, 4 times / day Route: oral Route: steady Dose: 50 mg, 4 times / day Sources: |
unhealthy, 46.6 years (range: 25 - 65 years) Health Status: unhealthy Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Sources: |
|
| Headache | 50 mg 4 times / day steady, oral Highest studied dose Dose: 50 mg, 4 times / day Route: oral Route: steady Dose: 50 mg, 4 times / day Sources: |
unhealthy, 46.6 years (range: 25 - 65 years) Health Status: unhealthy Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Sources: |
|
| Nausea | 50 mg 4 times / day steady, oral Highest studied dose Dose: 50 mg, 4 times / day Route: oral Route: steady Dose: 50 mg, 4 times / day Sources: |
unhealthy, 46.6 years (range: 25 - 65 years) Health Status: unhealthy Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Income-, education- and gender-related inequalities in out-of-pocket health-care payments for 65+ patients - a systematic review. | 2010-08-11 |
|
| Medical management of overactive bladder. | 2010-04 |
|
| Oxybutynin extended release for the management of overactive bladder: a clinical review. | 2009-09-21 |
|
| Anticholinergics for urinary symptoms in multiple sclerosis. | 2009-01-21 |
|
| [Randomized, placebo-controlled, double blind clinical trial for the evaluation of the efficacy and safety of oral methantheliniumbromide (Vagantin) in the treatment of focal hyperhidrosis]. | 2004-05 |
|
| [Oral anticholinergic therapy of focal hyperhidrosis with methanthelinium bromide (Vagantin). Initial data on effectiveness]. | 2002-02 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=25057361
Banthine at a dose of 50–100 mg every 4 h in patients with palmar hyperhidrosis
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8750900
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
Created
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Wed Apr 02 08:40:18 GMT 2025
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Wed Apr 02 08:40:18 GMT 2025
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090519SAPF
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Validated (UNII)
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C29704
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ACTIVE MOIETY |