Domiphen

Identification

Name
Domiphen
Accession Number
DB11594
Type
Small Molecule
Groups
Approved, Experimental
Description

Domiphen bromide is a topical antiseptic and a quaternary ammonium compound.

Structure
Thumb
Synonyms
  • (beta-phenoxyethyl)dimethyldodecylammonium
  • 1-dodecanaminium, n,n-dimethyl-n-(2-phenoxyethyl)
  • Dodecyldimethyl(2-phenoxyethyl)ammonium
  • Domiphen cation
  • Domiphen ion
  • Phenododecinium
Product Ingredients
IngredientUNIICASInChI Key
Domiphen bromideR4CY19YS7C538-71-6OJIYIVCMRYCWSE-UHFFFAOYSA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antiseptique Pastille 1.5mg CeriseLozenge1.5 mgOralProdemdis Enr.1991-12-312010-07-15Canada
Antiseptique Pastille 1.5mg CitronLozenge1.5 mgOralProdemdis Enr.1991-12-312010-07-15Canada
Antiseptique Pastille 1.5mg MentheLozenge1.5 mgOralProdemdis Enr.1991-12-312010-07-15Canada
Antiseptique Pastille 1.5mg Miel EucalyptusLozenge1.5 mgOralProdemdis Enr.1991-12-312010-07-15Canada
Bronchodex Pastille 1.5mg Miel EucLozenge1.5 mgOralProdemdis Enr.1989-12-312010-07-15Canada
Bronchodex Pastilles 1.5mg Saveur CeriseLozenge1.5 mgOralProdemdis Enr.1983-12-312010-07-15Canada
Bronchodex Pastilles 1.5mg Saveur CitronLozenge1.5 mgOralProdemdis Enr.1984-12-312010-07-15Canada
Bronchodex Pastilles 1.5mg Saveur MentheLozenge1.5 mgOralProdemdis Enr.1983-12-312010-07-15Canada
Ora-septic Cerises Loz 1.5mgLozenge1.5 mgOralProdemdis Enr.1989-12-312000-08-03Canada
Oraseptic Pastille Antisep 1.5mg CitronLozenge1.5 mgOralProdemdis Enr.1991-12-312000-08-03Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Exoden PowderDomiphen bromide (0.3 1/70g) + Cetylpyridinium chloride (0.084 g/70g)PowderTopicalLifeon Corp.2016-04-07Not applicableUs
Lander Orl Hygienic Mwh and GargleDomiphen bromide (1.5 mg) + Cetylpyridinium chloride (7.5 mg)MouthwashOralLander Co. Canada Limited1971-12-311997-08-11Canada
Mouthwash and GargleDomiphen bromide (.005 %) + Cetylpyridinium chloride (.025 %)MouthwashOralScott Chemical Canada1979-12-311997-08-12Canada
Nupercainal Antiseptic CreamDomiphen bromide (0.05 %) + Cinchocaine (0.5 %)CreamTopicalGlaxosmithkline Inc1967-12-31Not applicableCanada
Ultraplast Alginate Styptic GauzeDomiphen bromide (.15 %) + Sodium alginate (4 %) + Calcium alginate (5.5 %)DressingTopicalWallace, Cameron and Company Ltd.1969-12-311996-09-20Canada
Categories
UNII
4AZL56CU0F
CAS number
13900-14-6
Weight
Average: 334.567
Monoisotopic: 334.310441332
Chemical Formula
C22H40NO
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

Pharmacology

Indication

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

Associated Conditions
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:4545746]
  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. [PubMed:6381338]
External Links
PubChem Compound
3149
PubChem Substance
347828001
ChemSpider
3037
ChEBI
135978
ChEMBL
CHEMBL1187011
Wikipedia
Domiphen
ATC Codes
A01AB06 — Domiphen
AHFS Codes
  • 52:04.92 — Miscellaneous Anti-infectives
  • 84:04.92 — Miscellaneous Local Anti-infectives

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LozengeOral1.5 mg
PowderTopical
MouthwashOral
CreamTopical
DressingTopical.15 %
DressingTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.8e-06 mg/mLALOGPS
logP3.1ALOGPS
logP2.55ChemAxon
logS-7.9ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity117.14 m3·mol-1ChemAxon
Polarizability44.63 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

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
Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Quaternary ammonium salt / Tetraalkylammonium salt / Ether / Organic salt / Organic nitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on May 18, 2016 14:20 / Updated on November 12, 2018 07:37