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
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
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 |
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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) n = 34 Health Status: unhealthy Condition: detrusor hyperreflexia Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Population Size: 34 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) n = 34 Health Status: unhealthy Condition: detrusor hyperreflexia Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Population Size: 34 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) n = 34 Health Status: unhealthy Condition: detrusor hyperreflexia Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Population Size: 34 Sources: |
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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) n = 34 Health Status: unhealthy Condition: detrusor hyperreflexia Age Group: 46.6 years (range: 25 - 65 years) Sex: M+F Population Size: 34 Sources: |
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.
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NCI_THESAURUS |
C29704
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WHO-VATC |
QA03AB07
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WHO-ATC |
A03AB07
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4097
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5818-17-7
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SUB03209MIG
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DTXSID7046964
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C084588
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1736
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METHANTHELINE
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6821
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DB00940
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36EI79TX7I
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C83951
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100000085929
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)