NAV

Piperonyl butoxide

Identification

Summary

Piperonyl butoxide is a pesticide used as a potentiator ingredient in the treatment of pediculosis (head lice, body lice or crabs) to boost efficacy of treatment.

Brand Names
Pronto Plus, Rid
Generic Name
Piperonyl butoxide
DrugBank Accession Number
DB09350
Background

Piperonyl butoxide (PBO) is an organic compound used as a component of pesticide formulations. 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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
3D
Similar Structures
Weight
Average: 338.4385
Monoisotopic: 338.20932407
Chemical Formula
C19H30O5
Synonyms
Not Available
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Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatBody liceCombination Product in combination with: Pyrethrum extract (DB11087)••• •••
Used in combination to treatHead liceCombination Product in combination with: Pyrethrum extract (DB11087)••• •••
Used in combination to treatPubic liceCombination Product in combination with: Pyrethrum extract (DB11087)••• •••
Contraindications & Blackbox Warnings
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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.

Adverse Effects
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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.

Pathways
Not Available
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Not Available

Interactions

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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.
DrugInteraction
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interactions in your software
Tenofovir alafenamideThe serum concentration of Tenofovir alafenamide can be increased when it is combined with Piperonyl butoxide.
Food Interactions
No interactions found.

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Best Choice Lice KillingPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)ShampooTopicalValue Merchandisers2010-10-28Not applicableUS flag
Best Choice Lice treatmentPiperonyl butoxide (40 mg/1mL) + Pyrethrum extract (3.3 mg/1mL)KitTopicalValue Merchandisers2010-10-28Not applicableUS flag
Care One Lice KillingPiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)ShampooTopicalAmerican Sales Company2007-08-29Not applicableUS flag
Careone Complete Kit LicePiperonyl butoxide (4 g/100mL) + Pyrethrum extract (.33 g/100mL)KitTopicalAmerican Sales Company2019-01-26Not applicableUS flag
Careone LicePiperonyl butoxide (4 g/100mL) + Pyrethrum extract (0.33 g/100mL)Kit; ShampooTopicalAmerican Sales Company2007-09-262013-10-28US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Acetal / Aromatic heteropolycyclic compound / Benzenoid / Benzodioxole / Dialkyl ether / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Oxacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzodioxoles (CHEBI:32687) / Synergist (C18880)
Affected organisms
  • Head lice

Chemical Identifiers

UNII
LWK91TU9AH
CAS number
51-03-6
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  8. article [Link]
KEGG Drug
D08383
KEGG Compound
C18880
PubChem Compound
5794
PubChem Substance
310265223
ChemSpider
5590
BindingDB
181115
RxNav
8345
ChEBI
32687
ChEMBL
CHEMBL1201131
ZINC
ZINC000003875342
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Wikipedia
Piperonyl_butoxide
MSDS
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Clinical Trials

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PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
RinseTopical
LiquidTopical
Kit; shampooTopical
Aerosol; shampooTopical
KitTopical
OilTopical
GelTopical
ShampooTopical
Liquid; shampooTopical
AerosolTopical
SolutionTopical
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/MSsplash10-0570-7945000000-062bddba29790f597854
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-06r6-9411000000-2979e98bbce903cda515
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-08g0-9304000000-1c86345ee08568fa0c86
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-054o-9620000000-d512645fb92c367fdf58
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-2910000000-cb137878b0d303201145
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-054o-9600000000-8743a248c68d21f7155f
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.0412394
predicted
DarkChem Lite v0.1.0
[M-H]-198.8912394
predicted
DarkChem Lite v0.1.0
[M-H]-178.5391
predicted
DeepCCS 1.0 (2019)
[M+H]+182.6068857
predicted
DarkChem Lite v0.1.0
[M+H]+200.1807394
predicted
DarkChem Lite v0.1.0
[M+H]+180.96446
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.046048
predicted
DarkChem Lite v0.1.0
[M+Na]+199.1630394
predicted
DarkChem Lite v0.1.0
[M+Na]+187.36714
predicted
DeepCCS 1.0 (2019)

Drug created at November 27, 2015 23:20 / Updated at September 28, 2021 21:54