DIPHEMANIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24N
Molecular Weight	278.4113
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

C[N+]1(C)CCC(CC1)=C(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=LCTZPQRFOZKZNK-UHFFFAOYSA-N

InChI=1S/C20H24N/c1-21(2)15-13-19(14-16-21)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18/h3-12H,13-16H2,1-2H3/q+1

HIDE SMILES / InChI

Description
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01154a556

Diphemanil methylsulfate (Prantal), a quarternary amine, is a highly specific parasympathetic blocking agent.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D06878 \| https://www.ebi.ac.uk/chembl/compound/inspect/CHEMBL1201340 \| https://www.drugbank.ca/drugs/DB00729#targets	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6696291 https://www.ncbi.nlm.nih.gov/pubmed/13108465	Primary	Approved 8429	PRANTAL Approved Use Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.
Hyperhidrosis 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14888992	Primary	Approved 8429	PRANTAL Approved Use Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.
Peptic ulcer 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13002747 https://www.ncbi.nlm.nih.gov/pubmed/13002747 https://www.ncbi.nlm.nih.gov/pubmed/13065676 https://www.ncbi.nlm.nih.gov/pubmed/14926817	Primary	Approved 8429	PRANTAL Approved Use Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.
Bradycardias related to vagal hyper reflectivity 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17175143	Primary	Approved 8429	PRANTAL Approved Use Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.35 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1623915/	unknown, oral		DIPHEMANIL unknown	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8087216/	3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		DIPHEMANIL plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
2 mg single, respiratory Highest studied dose Dose: 2 mg Route: respiratory Route: single Dose: 2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6696291	unhealthy, 25 years (range: 19-40 years) n = 20 Health Status: unhealthy Condition: asymptomatic asthma Age Group: 25 years (range: 19-40 years) Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/6696291	Sources: https://pubmed.ncbi.nlm.nih.gov/6696291
2 % single, topical Highest studied dose Dose: 2 % Route: topical Route: single Dose: 2 % Sources: https://pubmed.ncbi.nlm.nih.gov/2190054	unhealthy, 27-66 years n = 15 Health Status: unhealthy Condition: Frey's syndrome Age Group: 27-66 years Sex: M+F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/2190054	Other AEs: Dry mouth... Other AEs: Dry mouth (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/2190054
250 mg single, oral Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1623915	healthy, 30.8 years (range: 26 -42 years) n = 6 Health Status: healthy Age Group: 30.8 years (range: 26 -42 years) Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/1623915	Other AEs: Dry mouth, Headache... Other AEs: Dry mouth (1 patient) Headache (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/1623915

AEs

AE	Significance	Dose	Population
Dry mouth	2 patients	2 % single, topical Highest studied dose Dose: 2 % Route: topical Route: single Dose: 2 % Sources: https://pubmed.ncbi.nlm.nih.gov/2190054	unhealthy, 27-66 years n = 15 Health Status: unhealthy Condition: Frey's syndrome Age Group: 27-66 years Sex: M+F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/2190054
Dry mouth	1 patient	250 mg single, oral Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1623915	healthy, 30.8 years (range: 26 -42 years) n = 6 Health Status: healthy Age Group: 30.8 years (range: 26 -42 years) Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/1623915
Headache	1 patient	250 mg single, oral Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1623915	healthy, 30.8 years (range: 26 -42 years) n = 6 Health Status: healthy Age Group: 30.8 years (range: 26 -42 years) Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/1623915

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00ECU3
ABI Chem	AC1L1LUR
AK Scientific	2381AH
AbovChem LLC	HY-16171
ApexBio Technology	A8414
AstaTech	C75961
BLD Pharm	BD125810
BOC Sciences	62-97-5
Chem Scene	CS-0906
ChemShuttle	141690
ChemTik	CTK5J1974
Chemieliva Pharmaceutical Co., Ltd	PBCM1197720
Compound Cloud	6126
Compound Cloud	6127
KeyOrganics	AS-67309
Lab Network	LN01285312
MedChem Express	HY-16171
MolPort	MolPort-003-666-719
MuseChem	A000461
Ryan Scientific	Melatonine
Selleck Chemicals	S4034
TargetMol	T0594
ZINC	ZINC000001482039	http://zinc15.docking.org/substances/ZINC000001482039
eMolecules	33507697
eNovation Chemicals	D389129
mcule	MCULE-3561653202
mcule	MCULE-8923880467

PubMed

Title	Date	PubMed
Prantal in the treatment of hyperhidrosis.	1951 Oct	14888992
Prantal in dermatology.	1952 May	14927985
Effect of inhaled diphemanil methylsulfate, a parasympatholytic agent, on histamine induced bronchoconstriction in asymptomatic asthmatics.	1984 Jan	6696291
Treatment of Frey's syndrome with topical 2% diphemanil methylsulfate (Prantal): a double-blind evaluation of 15 patients.	1990 Jun	2190054

Patents

Sample Use Guides

In Vivo Use Guide

Diphenylmethane methylsulfate was prescribed for the treatment of hyperhidrosis in a divided daily dosage of 200—400 mg. Fifteen patients with severe gustatory sweating after total parotidectomy and facial nerve preservation were alternatively treated with topically applied placebo and topically applied 2% diphemanil methylsulfate. 2 mg dose of diphemanil, administered by oral inhalation 20 minutes before histamine challenge, is ineffective in protecting against induced bronchospasm in asymptomatic adult asthmatics.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

DIPHEMANIL

Common Name

English

DIPHEMANIL ION

Common Name

English

PIPERIDINIUM, 4-(DIPHENYLMETHYLENE)-1,1-DIMETHYL-

Systematic Name

English

4-(DIPHENYLMETHYLENE)-1,1-DIMETHYLPIPERIDINIUM

Systematic Name

English

Diphemanil [WHO-DD]

Common Name

English

DIPHEMANIL CATION

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA03CA08