Identification

Generic Name
Lapyrium
DrugBank Accession Number
DB09376
Background

Lapyrium is a quaternary ammonium cation used as a surfactant, antistatic agent, and biocide in various cosmetic products 1. It is commonly found formulated as lapyrium chloride.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 363.521
Monoisotopic: 363.264219415
Chemical Formula
C21H35N2O3
Synonyms
Not Available

Pharmacology

Indication

Used as a surfactant, antistatic agent, and biocide in cosmetic products 1.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Lapyrium is a quaternary ammonium cation (QAC). QACs exert broad spectrum antimicrobial activity, acting as bactericidal agents 2.

Mechanism of action

As a QAC, lapyrium likely acts by associating with the negatively charged cell membrane of bacterial cells 2. This is followed by the insertion of the compound's side chain and subsequent disruption of the cell membrane. Ultimately this disruption leads to the leakage of cellular contents and cell lysis. QACs are typically more effective against Gram-positive bacteria as they only have one cell membrane.

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

Intravenous LD50 of 18mg/kg reported for mice 3. Oral LD50 estimated to be 8.2g/kg based on results with steapyrium chloride in rats due to the similarity in structre between steapyrium and lapyrium 1.

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
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Lapyrium chloride732T8851QH6272-74-8HPKFFZSXDWPVLX-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acid esters
Direct Parent
Fatty acid esters
Alternative Parents
Pyridinium derivatives / Heteroaromatic compounds / Secondary carboxylic acid amides / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 2 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Fatty acid ester / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
5172AI8LRR
CAS number
109260-82-4
InChI Key
UGJWZYARKOFRDB-UHFFFAOYSA-O
InChI
InChI=1S/C21H34N2O3/c1-2-3-4-5-6-7-8-9-11-14-21(25)26-18-15-22-20(24)19-23-16-12-10-13-17-23/h10,12-13,16-17H,2-9,11,14-15,18-19H2,1H3/p+1
IUPAC Name
1-({[2-(dodecanoyloxy)ethyl]carbamoyl}methyl)pyridin-1-ium
SMILES
CCCCCCCCCCCC(=O)OCCNC(=O)C[N+]1=CC=CC=C1

References

General References
  1. Authors unspecified: Final Report on the Safety Assessment of Steapyrium Chloride and Lapyrium Chloride Int J Toxicol. 1991 Jan 1;10(1):87-97. [Article]
  2. Jennings MC, Minbiole KP, Wuest WM: Quaternary Ammonium Compounds: An Antimicrobial Mainstay and Platform for Innovation to Address Bacterial Resistance. ACS Infect Dis. 2015 Jul 10;1(7):288-303. doi: 10.1021/acsinfecdis.5b00047. Epub 2015 May 29. [Article]
  3. ChemIDPlus: Lapyrium Chloride [Link]
PubChem Compound
22660
PubChem Substance
347827837
ChemSpider
21241
RxNav
28456
ChEBI
135534
ChEMBL
CHEMBL1201786
ZINC
ZINC000008214591
Wikipedia
Lapyrium
MSDS
Download (55.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityPartly solubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility9.66e-05 mg/mLALOGPS
logP1.59ALOGPS
logP0.16Chemaxon
logS-6.6ALOGPS
pKa (Strongest Acidic)12.73Chemaxon
pKa (Strongest Basic)-6.5Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area59.28 Å2Chemaxon
Rotatable Bond Count16Chemaxon
Refractivity104.34 m3·mol-1Chemaxon
Polarizability43.95 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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at November 30, 2015 19:10 / Updated at January 09, 2021 18:40