Cetrimonium

Identification

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Name
Cetrimonium
Accession Number
DB01718  (EXPT00048, DB13159)
Type
Small Molecule
Groups
Approved
Description

Cetrimonium is a quaternary ammonium cation whose salts are used as antiseptics.

Structure
Thumb
Synonyms
  • Cetrimonium cation
  • Cetrimonium ion
  • Cetyl-Trimethyl-Ammonium
  • Cetyltrimethylammonium
  • Cetyltrimethylammonium cation
  • Cetyltrimethylammonium ion
  • Hexadecyltrimethylammonium
  • Hexadecyltrimethylammonium cation
  • Hexadecyltrimethylammonium ion
  • N,N,N-Trimethyl-1-hexadecanaminium
  • Trimethylhexadecylammonium
External IDs
PB-300
Product Ingredients
IngredientUNIICASInChI Key
Cetrimonium bromideL64N7M9BWR57-09-0LZZYPRNAOMGNLH-UHFFFAOYSA-M
Cetrimonium carboxydecyl PEG-8 dimethicone0T3143V100Not AvailableNot applicable
Cetrimonium chlorideUC9PE95IBP112-02-7WOWHHFRSBJGXCM-UHFFFAOYSA-M
Cetrimonium hydroxide8Q7D6895LV505-86-2WJLUBOLDZCQZEV-UHFFFAOYSA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cetrimide Aqueous Soln 1%Liquid1 %TopicalIngram And Bell Inc.1960-12-311999-08-05Canada
Cetrimide Cream 0.5%Cream.5 %TopicalCanadian Custom Packaging Company1992-12-31Not applicableCanada
Cetrimide Tincture 0.5%Tincture.5 %TopicalCanadian Custom Packaging Company1990-12-31Not applicableCanada
Resdan Dandruff Treatment Liquid 1%Liquid; Shampoo1 %TopicalWyeth Ltd.1992-12-312005-07-28Canada
Savlon Crm 0.5%Cream.5 %TopicalWhitehall Robins Inc.1993-12-312002-07-19Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bye Bye Burn LotCetrimonium bromide (.1 %) + Allantoin (.1 %) + Benzocaine (.55 %) + Vitamin E (2 %)LotionTopicalDavid D. Daniels Ltd.1996-08-151998-01-15Canada
Chlorhexidine-cetrimide Soltn ConcCetrimonium bromide (15 %) + Chlorhexidine gluconate (1.5 %)LiquidTopicalBio Pharm, Inc.1989-12-311996-09-09Canada
Salvesept CrmCetrimonium bromide (.5 %) + Chlorhexidine gluconate (1 %)CreamTopicalProtector Canada Inc.1993-12-312012-06-18Canada
SavlodilCetrimonium bromide (0.15 %) + Chlorhexidine gluconate (0.015 %)SolutionTopicalRegent Medical Americas, Llc1993-12-312012-07-31Canada
Savlon Hospital ConcentrateCetrimonium bromide (15 %) + Chlorhexidine gluconate (1.5 %)LiquidTopicalDurex Canada, Division Of Ssl Canada Inc.1993-12-312005-07-14Canada
Xylonor - Aem AspCetrimonium bromide (150 mg) + Lidocaine (15 g)Aerosol, metered; SprayTopicalSeptodont1997-03-26Not applicableCanada
Xylonor GelCetrimonium bromide (150 mg) + Lidocaine (5 g)GelTopicalSeptodont1981-12-31Not applicableCanada
Xylonor SprayCetrimonium bromide (150 mg) + Lidocaine (15 g)AerosolTopicalSeptodont1976-12-311998-04-16Canada
Categories
UNII
Z7FF1XKL7A
CAS number
6899-10-1
Weight
Average: 284.5435
Monoisotopic: 284.331725349
Chemical Formula
C19H42N
InChI Key
RLGQACBPNDBWTB-UHFFFAOYSA-N
InChI
InChI=1S/C19H42N/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4/h5-19H2,1-4H3/q+1
IUPAC Name
hexadecyltrimethylazanium
SMILES
CCCCCCCCCCCCCCCC[N+](C)(C)C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCyclopropane mycolic acid synthase MmaA2Not AvailableMycobacterium tuberculosis
UCyclopropane mycolic acid synthase 1Not AvailableMycobacterium tuberculosis
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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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
Not Available
External Links
KEGG Drug
D03454
KEGG Compound
C11275
PubChem Compound
2681
PubChem Substance
46507665
ChemSpider
2580
BindingDB
58941
ChEBI
39561
ChEMBL
CHEMBL1183605
HET
16A
Wikipedia
Cetrimonium
ATC Codes
D08AJ04 — CetrimideD11AC01 — CetrimideR02AA17 — CetrimoniumD08AJ02 — Cetrimonium
AHFS Codes
  • 84:04.92 — Miscellaneous Local Anti-infectives
PDB Entries
1kpg / 1tpy / 3b00 / 3hf0 / 3p73 / 5hxw

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LotionTopical
LiquidTopical1 %
CreamTopical.5 %
TinctureTopical.5 %
LiquidTopical
Liquid; shampooTopical1 %
CreamTopical
SolutionTopical
Aerosol, metered; sprayTopical
GelTopical
AerosolTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)240 °CPhysProp
water solubility1E+005 mg/LMERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility5.24e-06 mg/mLALOGPS
logP2.48ALOGPS
logP2.69ChemAxon
logS-7.8ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity104.99 m3·mol-1ChemAxon
Polarizability41.09 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8956
Blood Brain Barrier+0.9693
Caco-2 permeable+0.7014
P-glycoprotein substrateNon-substrate0.5098
P-glycoprotein inhibitor INon-inhibitor0.9556
P-glycoprotein inhibitor IINon-inhibitor0.7862
Renal organic cation transporterNon-inhibitor0.6184
CYP450 2C9 substrateNon-substrate0.8557
CYP450 2D6 substrateNon-substrate0.6596
CYP450 3A4 substrateSubstrate0.5059
CYP450 1A2 substrateNon-inhibitor0.8243
CYP450 2C9 inhibitorNon-inhibitor0.947
CYP450 2D6 inhibitorNon-inhibitor0.9149
CYP450 2C19 inhibitorNon-inhibitor0.9266
CYP450 3A4 inhibitorNon-inhibitor0.9831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9722
Ames testNon AMES toxic0.9617
CarcinogenicityCarcinogens 0.7243
BiodegradationReady biodegradable0.8286
Rat acute toxicity2.8455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8233
hERG inhibition (predictor II)Non-inhibitor0.5139
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Quaternary ammonium salts
Direct Parent
Tetraalkylammonium salts
Alternative Parents
Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Amines / Organic cations
Substituents
Tetraalkylammonium salt / Organopnictogen compound / Hydrocarbon derivative / Organic salt / Amine / Organic cation / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
quaternary ammonium ion (CHEBI:39561) / a cation (CPD-13595)

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Methyltransferase activity
Specific Function
Catalyzes the conversion of a double bond to a cis cyclopropane ring at the distal position of an alpha mycolic acid via the transfer of a methylene group from S-adenosyl-L-methionine. MmaA2 also c...
Gene Name
mmaA2
Uniprot ID
Q79FX6
Uniprot Name
Cyclopropane mycolic acid synthase MmaA2
Molecular Weight
32724.06 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the conversion of a double bond to a cyclopropane ring at the distal position of an alpha mycolic acid via the transfer of a methylene group from S-adenosyl-L-methionine. Cyclopropanated mycolic acids are key factors participating in cell envelope permeability, host immunomodulation and persistence.
Specific Function
Cyclopropane-fatty-acyl-phospholipid synthase activity
Gene Name
cmaA1
Uniprot ID
P9WPB7
Uniprot Name
Cyclopropane mycolic acid synthase 1
Molecular Weight
32460.98 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on July 21, 2019 06:33