Domiphen

Identification

Generic Name

Domiphen

DrugBank Accession Number

DB11594

Background

Domiphen bromide is a quaternary ammonium compound that is predominantly employed as a topically administered antiseptic agent.

Type

Small Molecule

Groups

Approved, Experimental

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Domiphen (DB11594)

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Weight

Average: 334.567
Monoisotopic: 334.310441332

Chemical Formula

C₂₂H₄₀NO

Synonyms

• (beta-phenoxyethyl)dimethyldodecylammonium
• 1-dodecanaminium, n,n-dimethyl-n-(2-phenoxyethyl)
• Dodecyldimethyl(2-phenoxyethyl)ammonium
• Domiphen cation
• Domiphen ion
• Phenododecinium

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Pharmacology

Indication

Anti-infective (topical), it is used for the treatment of Acute Infectious Dental Diseases and other conditions.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination for symptomatic treatment of	Hemorrhoids	Combination Product in combination with: Cinchocaine (DB00527)	••••••••••••

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Pharmacodynamics

The efficacy and tolerability of domiphen bromide (domifen bromide), administered at a dosage of 0.5 mg every 4-6 hr in a double-blind placebo controlled study in 31 patients affected by acute infectious dental diseases, are described. After 2 days of treatment with the drug, there was a significant decrease in pain and inflammation. The drug elicited a good response, improved prognosis and reduced the number of days of illness.

Mechanism of action

Domiphen bromide is a quaternary antiseptic with actions and uses similar to those of cationic surfactants.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Domiphen bromide	R4CY19YS7C	538-71-6	OJIYIVCMRYCWSE-UHFFFAOYSA-M

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Antiseptique Pastille 1.5mg Cerise	Lozenge	1.5 mg / loz	Oral	Prodemdis Enr.	1991-12-31	2010-07-15
Antiseptique Pastille 1.5mg Citron	Lozenge	1.5 mg / loz	Oral	Prodemdis Enr.	1991-12-31	2010-07-15
Antiseptique Pastille 1.5mg Menthe	Lozenge	1.5 mg / loz	Oral	Prodemdis Enr.	1991-12-31	2010-07-15
Antiseptique Pastille 1.5mg Miel Eucalyptus	Lozenge	1.5 mg / loz	Oral	Prodemdis Enr.	1991-12-31	2010-07-15
Bronchodex Pastille 1.5mg Miel Euc	Lozenge	1.5 mg / loz	Oral	Prodemdis Enr.	1989-12-31	2010-07-15

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Exoden Powder	Domiphen bromide (0.12 1/100g) + Cetylpyridinium chloride (0.043 g/100g)	Powder	Topical	Lifeon Corp.	2021-03-09	Not applicable
Exoden Powder	Domiphen bromide (0.3 1/70g) + Cetylpyridinium chloride (0.084 g/70g)	Powder	Topical	Lifeon Corp.	2016-04-07	2019-09-26
INALAR RAFFREDDORE	Domiphen bromide (0.025 g/100ml) + Xylometazoline hydrochloride (0.1 g/100ml)	Aerosol, spray	Respiratory (inhalation)	Farmakopea S.P.A.	2014-07-08	2016-06-12
INALAR RAFFREDDORE	Domiphen bromide (0.025 g/100ml) + Xylometazoline hydrochloride (0.1 g/100ml)	Aerosol, spray	Respiratory (inhalation)	Farmakopea S.P.A.	2014-07-08	2016-06-12
INALAR RAFFREDDORE	Domiphen bromide (0.025 g/100mL) + Xylometazoline (0.1 g/100mL)	Spray	Nasal	Farmakopea S.P.A.	2014-07-08	2022-07-02

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Exoden Powder	Domiphen bromide (0.12 1/100g) + Cetylpyridinium chloride (0.043 g/100g)	Powder	Topical	Lifeon Corp.	2021-03-09	Not applicable
Exoden Powder	Domiphen bromide (0.3 1/70g) + Cetylpyridinium chloride (0.084 g/70g)	Powder	Topical	Lifeon Corp.	2016-04-07	2019-09-26

Categories

ATC Codes

A01AB06 — Domiphen

• A01AB — Antiinfectives and antiseptics for local oral treatment
• A01A — STOMATOLOGICAL PREPARATIONS
• A01 — STOMATOLOGICAL PREPARATIONS
• A — ALIMENTARY TRACT AND METABOLISM

Drug Categories

• Alimentary Tract and Metabolism
• Amines
• Ammonium Compounds
• Anti-Infective Agents, Local
• Antiinfectives and Antiseptics for Local Oral Treatment
• Miscellaneous Anti-infectives
• Miscellaneous Local Anti-infectives
• Nitrogen Compounds
• Onium Compounds
• Stomatological Preparations

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Phenoxy compounds / Alkyl aryl ethers / Tetraalkylammonium salts / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Amines / Organic cations

Substituents

Alkyl aryl ether / Amine / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic cation / Organic nitrogen compound / Organic oxygen compound / Organic salt

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII

4AZL56CU0F

CAS number

13900-14-6

InChI Key

YXUPZGKORWTXID-UHFFFAOYSA-N

InChI

InChI=1S/C22H40NO/c1-4-5-6-7-8-9-10-11-12-16-19-23(2,3)20-21-24-22-17-14-13-15-18-22/h13-15,17-18H,4-12,16,19-21H2,1-3H3/q+1

IUPAC Name

dodecyldimethyl(2-phenoxyethyl)azanium

SMILES

CCCCCCCCCCCC[N+](C)(C)CCOC1=CC=CC=C1

References

General References

1. Egashira T, Nakagawa K, Shimamoto M, Kaneko O, Sadaoka K: Proceedings: Pharmacological study of dodecyl dimethyl-2-phenoxyethyl ammonium bromide (domiphen). Jpn J Pharmacol. 1974;24(0):s:37. [Article]
2. Scaglione F, Coduri M, Nebuloni R, Fraschini F: Activity and tolerability of domifen bromide in patients affected by acute infectious dental diseases: a double-blind placebo-controlled trial. Int J Clin Pharmacol Res. 1983;3(5):357-61. [Article]

External Links

PubChem Compound

3149

PubChem Substance

347828001

ChemSpider

3037

RxNav

23623

ChEBI

135978

ChEMBL

CHEMBL1187011

ZINC

ZINC000006845992

Wikipedia

Domiphen

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Recruiting	Treatment	Acute Vulvovaginal Candidiasis	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral
Lozenge	Oral	1.5 mg / loz
Lozenge	Oral
Powder	Topical
Aerosol, spray	Respiratory (inhalation)
Spray	Nasal
Mouthwash	Oral
Cream	Topical
Dressing	Topical	.15 %
Dressing	Topical

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.8e-06 mg/mL	ALOGPS
logP	3.1	ALOGPS
logP	2.55	Chemaxon
logS	-7.9	ALOGPS
pKa (Strongest Basic)	-4.9	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	1	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	9.23 Å2	Chemaxon
Rotatable Bond Count	15	Chemaxon
Refractivity	117.14 m3·mol-1	Chemaxon
Polarizability	44.63 Å3	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-004i-9540000000-64a1cc42b04f889bde5d
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	190.06267	predicted	DeepCCS 1.0 (2019)
[M+H]+	192.42068	predicted	DeepCCS 1.0 (2019)
[M+Na]+	198.64491	predicted	DeepCCS 1.0 (2019)

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Drug created at May 18, 2016 20:20 / Updated at April 16, 2024 12:20