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Details

Stereochemistry ACHIRAL
Molecular Formula C21H26NO3
Molecular Weight 340.4368
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)C1c2ccccc2Oc3ccccc31

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
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P25021
Gene ID: 3274.0
Gene Symbol: HRH2
Target Organism: Homo sapiens (Human)
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
25 ng/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
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

Doses

DosePopulationAdverse 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...
Other AEs:
Dry mouth
Headache
Nausea
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
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:
PubMed

PubMed

TitleDatePubMed
Oxybutynin extended release for the management of overactive bladder: a clinical review.
2009 Sep 21
Medical management of overactive bladder.
2010 Apr
Income-, education- and gender-related inequalities in out-of-pocket health-care payments for 65+ patients - a systematic review.
2010 Aug 11
Patents

Sample Use Guides

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.
Name Type Language
METHANTHELINE
VANDF  
Common Name English
METHANTHELINIUM
WHO-DD  
Common Name English
METHANTHELINE CATION
Common Name English
METHANTHELINE [VANDF]
Common Name English
ETHANAMINIUM, N,N-DIETHYL-N-METHYL-2-((9H-XANTHEN-9-YLCARBONYL)OXY)
Common Name English
METHANTHELINIUM [WHO-DD]
Common Name English
METHANTHELINE ION
Common Name English
DIETHYL(2-HYDROXYETHYL)METHYLAMMONIUM XANTHENE-9-CARBOXYLATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
WHO-VATC QA03AB07
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
WHO-ATC A03AB07
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
Code System Code Type Description
PUBCHEM
4097
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
CAS
5818-17-7
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
EVMPD
SUB03209MIG
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
EPA CompTox
5818-17-7
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
MESH
C084588
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
DRUG CENTRAL
1736
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
WIKIPEDIA
METHANTHELINE
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
RXCUI
6821
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00940
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
FDA UNII
36EI79TX7I
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY
NCI_THESAURUS
C83951
Created by admin on Sat Jun 26 12:16:12 UTC 2021 , Edited by admin on Sat Jun 26 12:16:12 UTC 2021
PRIMARY