Piperonyl butoxide

Identification

Name
Piperonyl butoxide
Accession Number
DB09350
Type
Small Molecule
Groups
Approved, Vet approved
Description

Piperonyl butoxide (PBO) is an organic compound used as a component of pesticide formulations. It is a waxy white solid. It is used for the treatment of head, pubic (crab), and body lice. Piperonyl butoxide is a synergist. It has no pesticidal activity of its own, but acts to increase the activity of pesticides such as carbamates, pyrethrins, pyrethroids, and rotenone. Piperonyl butoxide is a semisynthetic derivative of safrole.

Structure
Thumb
Synonyms
Not Available
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Best Choice Lice KillingPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)ShampooTopicalValue Merchandisers2010-10-28Not applicableUs
Care One Lice KillingPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)ShampooTopicalAmerican Sales Company2007-08-29Not applicableUs
Careone LicePiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)KitAmerican Sales Company2007-09-262019-01-21Us
CareOne Lice SolutionPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)KitAmerican Sales Company2016-04-29Not applicableUs
Complete Lice TreatmentPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)KitMeijer Distribution2007-09-122015-10-01Us
CVS 3 Step Lice SolutionPiperonyl butoxide (40 mg/1mL) + Pyrethrum extract (3.3 mg/1mL)KitTopicalCVS Health2010-10-28Not applicableUs
CVS Health Lice KillingPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)ShampooTopicalCVS Health2010-10-28Not applicableUs
Dg Health Lice Killing Maximum StrengthPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)ShampooTopicalDolgencorp2010-01-082012-08-18Us
Discount Drug Mart Lice KillingPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)ShampooTopicalDiscount Drug Mart2010-10-28Not applicableUs
Eco.kidPiperonyl butoxide (2 mL/100mL) + Pyrethrum extract (0.17 mL/100mL)ShampooTopicalFravin Pty Ltd2011-10-01Not applicableUs
Categories
UNII
LWK91TU9AH
CAS number
51-03-6
Weight
Average: 338.4385
Monoisotopic: 338.20932407
Chemical Formula
C19H30O5
InChI Key
FIPWRIJSWJWJAI-UHFFFAOYSA-N
InChI
InChI=1S/C19H30O5/c1-3-5-7-20-8-9-21-10-11-22-14-17-13-19-18(23-15-24-19)12-16(17)6-4-2/h12-13H,3-11,14-15H2,1-2H3
IUPAC Name
5-{[2-(2-butoxyethoxy)ethoxy]methyl}-6-propyl-2H-1,3-benzodioxole
SMILES
CCCCOCCOCCOCC1=CC2=C(OCO2)C=C1CCC

Pharmacology

Indication

For the treatment of head, pubic (crab), and body lice.

Associated Conditions
Pharmacodynamics

Piperonyl butoxide does not affect the mixed-function oxidase system in humans. In small trials in human volunteers, usual doses of piperonyl butoxide had no effect on humans.

Mechanism of action

Piperonyl butoxide is not a pesticide, but acts as a synergist to increase the activity of pesticides such as carbamates, pyrethrins, pyrethroids, and rotenone. Piperonyl butoxide inhibits the mixed-function oxidase (MFO) system of an insect. The MFO system is the insects natural defense system and causes the oxidative breakdown of insecticides. Thus, by inhibiting this system piperonyl butoxide promotes higher levels of insecticide and allows for lower doses to be used for a lethal effect.

Absorption

Piperonyl butoxide is applied topically. In a study evaluating the 7-day urinary accumulation of piperonyl butoxide after topical application, it was found that approximately 2% of the dose was absorbed through the skin. The percutaneous absorption when applied to the scalp was found to be 8.3%.

Volume of distribution

Piperonyl butoxide is minimally absorbed in humans. Volume of distribution has not been studied.

Protein binding

Piperonyl butoxide is minimally absorbed in humans. Protein binding has not been studied.

Metabolism

Piperonyl butoxide is minimally absorbed in humans. Metabolism has not been studied.

Route of elimination

In an absorption study in human volunteers, it was found that, if absorbed, piperonyl butoxide was eliminated in urine.

Half life

32 hours.

Clearance

Clearance of piperonyl butoxide has not been studied.

Toxicity

The acute oral LD50 for rats is 4,570 to 12,800 mg/kg and 2,700 to 5,300 mg/kg for rabbits. It is low to very low in toxicity when ingested by mammals.

Affected organisms
  • Head lice
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
No interactions found.

References

General References
  1. Wester RC, Bucks DA, Maibach HI: Human in vivo percutaneous absorption of pyrethrin and piperonyl butoxide. Food Chem Toxicol. 1994 Jan;32(1):51-3. [PubMed:8132164]
  2. Lopatina IuV, Eremina OIu, Iakovlev EA: [Pyrethroid resistance mechanisms in the body lice Pediculus humanus humanus L.: detoxification enzyme systems]. Med Parazitol (Mosk). 2014 Jan-Mar;(1):19-24. [PubMed:24738222]
  3. Durand R, Bouvresse S, Berdjane Z, Izri A, Chosidow O, Clark JM: Insecticide resistance in head lice: clinical, parasitological and genetic aspects. Clin Microbiol Infect. 2012 Apr;18(4):338-44. doi: 10.1111/j.1469-0691.2012.03806.x. [PubMed:22429458]
  4. Barker SC, Altman PM: A randomised, assessor blind, parallel group comparative efficacy trial of three products for the treatment of head lice in children--melaleuca oil and lavender oil, pyrethrins and piperonyl butoxide, and a "suffocation" product. BMC Dermatol. 2010 Aug 20;10:6. doi: 10.1186/1471-5945-10-6. [PubMed:20727129]
  5. Wendel K, Rompalo A: Scabies and pediculosis pubis: an update of treatment regimens and general review. Clin Infect Dis. 2002 Oct 15;35(Suppl 2):S146-51. [PubMed:12353201]
  6. Meinking TL, Serrano L, Hard B, Entzel P, Lemard G, Rivera E, Villar ME: Comparative in vitro pediculicidal efficacy of treatments in a resistant head lice population in the United States. Arch Dermatol. 2002 Feb;138(2):220-4. [PubMed:11843643]
  7. Queiroz MC, Sato ME: Pyrethroid resistance in Phytoseiulus macropilis (Acari: Phytoseiidae): cross-resistance, stability and effect of synergists. Exp Appl Acarol. 2016 Jan;68(1):71-82. doi: 10.1007/s10493-015-9984-2. Epub 2015 Nov 3. [PubMed:26530989]
  8. article [Link]
External Links
KEGG Drug
D08383
KEGG Compound
C18880
PubChem Compound
5794
PubChem Substance
310265223
ChemSpider
5590
BindingDB
181115
ChEBI
32687
ChEMBL
CHEMBL1201131
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Piperonyl_butoxide
MSDS
Download (53.9 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
RinseTopical
Kit
Aerosol; shampooTopical
OilTopical
GelTopical
Liquid; shampooTopical
ShampooTopical
KitTopical
AerosolTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00611 mg/mLALOGPS
logP3.07ALOGPS
logP4.1ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.15 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity93.6 m3·mol-1ChemAxon
Polarizability40.43 Å3ChemAxon
Number of Rings2ChemAxon
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
Mass Spectrum (Electron Ionization)MSsplash10-004i-3900000000-edf43c4a8ef3e628b1f3
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodioxoles
Sub Class
Not Available
Direct Parent
Benzodioxoles
Alternative Parents
Benzenoids / Oxacyclic compounds / Dialkyl ethers / Acetals / Hydrocarbon derivatives
Substituents
Benzodioxole / Benzenoid / Oxacycle / Ether / Dialkyl ether / Acetal / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aromatic heteropolycyclic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzodioxoles (CHEBI:32687) / Synergist (C18880)

Drug created on November 27, 2015 16:20 / Updated on November 02, 2018 07:02