DIPHEMANIL METHYLSULFATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24N.CH3O4S
Molecular Weight	389.508
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COS([O-])(=O)=O.C[N+]1(C)CCC(CC1)=C(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=BREMLQBSKCSNNH-UHFFFAOYSA-M

InChI=1S/C20H24N.CH4O4S/c1-21(2)15-13-19(14-16-21)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18;1-5-6(2,3)4/h3-12H,13-16H2,1-2H3;1H3,(H,2,3,4)/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	CH3O4S
Molecular Weight	111.097
Charge	-1
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H24N
Molecular Weight	278.4113
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

Description

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	Antagonist 2,778

Conditions

Condition	Modality	Highest Phase	Product
Asthma 241	Primary	Approved 8,429	PRANTAL
Hyperhidrosis 4	Primary	Approved 8,429	PRANTAL
Peptic ulcer 72	Primary	Approved 8,429	PRANTAL
Bradycardias related to vagal hyper reflectivity 2	Primary	Approved 8,429	PRANTAL

C_max

Value	Dose	Co-administered	Analyte	Population
47.9 μg/L	250 mg single, oral		DIPHEMANIL plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
433 μg × h/L	250 mg single, oral		DIPHEMANIL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.35 h	250 mg single, oral		DIPHEMANIL plasma	Homo sapiens
8.6 h	3 mg/kg single, oral		DIPHEMANIL plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
2 mg single, respiratory Highest studied dose	unhealthy, 25 years (range: 19-40 years)
2 % single, topical Highest studied dose	unhealthy, 27-66 years	Other AEs: Dry mouth...
250 mg single, oral	healthy, 30.8 years (range: 26 -42 years)	Other AEs: Dry mouth, Headache...

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AEs

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AE	Significance	Dose	Population
Dry mouth	2 patients	2 % single, topical Highest studied dose	unhealthy, 27-66 years
Dry mouth	1 patient	250 mg single, oral	healthy, 30.8 years (range: 26 -42 years)
Headache	1 patient	250 mg single, oral	healthy, 30.8 years (range: 26 -42 years)

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00ECU3
ABI Chem	AC1L1LUR
AbovChem LLC	HY-16171
AK Scientific	2381AH
ApexBio Technology	A8414

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PubMed

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Title	Date	PubMed
Effect of inhaled diphemanil methylsulfate, a parasympatholytic agent, on histamine induced bronchoconstriction in asymptomatic asthmatics.	1984 Jan	6696291

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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

Substance Class	Chemical
Record UNII	W2ZG23MGYI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIPHEMANIL METHYLSULFATE

Common Name

English

NSC-41725

Code

English

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

Common Name

English

DIPHEMANIL METHYLSULFATE [GREEN BOOK]

Common Name

English

4-(DIPHENYLMETHYLENE)-1,1-DIMETHYLPIPERIDINIUM METHYL SULPHATE

Systematic Name

English

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Classification Tree

Code System

Code

Subpart C--New Drugs Exempted From Prescription-Dispensing Requirements

CFR

21 CFR 310.201

Anticholinergic Agent

NCI_THESAURUS

C29704

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Code System

Code

Type

Description

CAS

62-97-5

PRIMARY

WIKIPEDIA

DIPHEMANIL METILSULFATE

PRIMARY

NSC

41725

PRIMARY

EVMPD

SUB07208MIG

PRIMARY

FDA UNII

W2ZG23MGYI

PRIMARY

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Related Record

Type

Details


					R24I7CLU7K

METHYL SULFATE

PARENT -> SALT/SOLVATE


					Q26TX1UD0W

DIPHEMANIL

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					Q26TX1UD0W

DIPHEMANIL

ACTIVE MOIETY

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="http://pubs.acs.org/doi/abs/10.1021/ja01154a556">http://pubs.acs.org/doi/abs/10.1021/ja01154a556</a></span></span></div></div>

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

Description

C_max

T_1/2