U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H30O5
Molecular Weight 338.4385
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPERONYL BUTOXIDE

SMILES

CCCCOCCOCCOCC1=CC2=C(OCO2)C=C1CCC

InChI

InChIKey=FIPWRIJSWJWJAI-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H30O5
Molecular Weight 338.4385
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Piperonyl butoxide (PBO) is an organic compound used as a component of pesticide formulations. It is a waxy white solid. It is a semisynthetic derivative of safrole. 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. PBO acts as an insecticide synergist by inhibiting the natural defense mechanisms of the insect, the most important of which is the Mixed Function Oxidase system, also known as the cytochrome P-450 system. The MFO system is the primary route of detoxification in insects, and causes the oxidative breakdown of insecticides like pyrethrins and the synthetic pyrethroids - thus when PBO is added, higher insecticide levels remain in the insect to exercise their lethal effect. An important consequence of this property is that, by enhancing the activity of a given insecticide, less may be used to achieve the same result. PBO does not appear to have a significant effect on the MFO system in humans. Skin Sensitization PBO has a low acute toxicity by oral, inhalation and dermal routes. It is minimally irritating to the eyes and skin. It is a not a dermal sensitizer. No evidence suggests that PBO disrupts the normal functioning of the endocrine system. This includes the recently developed data to assess the possible interaction of PBO with the endocrine system.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
RID MOUSSE

Approved Use

Rid is a mousse designed to kill head, pubic (crab), and body lice.

Launch Date

9.523008E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
24 h
500 mg/kg single, oral
dose: 500 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIPERONYL BUTOXIDE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Susceptibility of populations of Banks grass mites (Acari: Tetranychidae) suspected of developing bifenthrin resistance from three maize fields.
2002
Characterization of resistance to clofentezine in populations of European red mite from orchards in Ontario.
2002
Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals.
2002 Dec
Efficacy of ethiprole applied alone and in combination with conventional insecticides for protection of stored wheat and stored corn.
2002 Dec
Impact of an insecticide resistance strategy for house fly (Diptera: Muscidae) control in intensive animal units in the United Kingdom.
2002 Dec
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.
2002 Dec
Fenbendazole pharmacokinetics, metabolism, and potentiation in horses.
2002 Nov
Effects of iprodione and fludioxonil on glycerol synthesis and hyphal development in Candida albicans.
2002 Oct
Near UV quantum yields for rotenone and piperonyl butoxide.
2002 Oct
Efficacy of the organic-certified insecticide Diatect II against the boll weevil (Anthonomus grandis) in cotton.
2002 Oct
The in vivo pediculicidal efficacy of a natural remedy.
2002 Oct
Oxidation of dibenzo- p-dioxin, dibenzofuran, biphenyl, and diphenyl ether by the white-rot fungus Phlebia lindtneri.
2002 Oct
Scabies and pediculosis pubis: an update of treatment regimens and general review.
2002 Oct 15
Insecticide susceptibilities of cat fleas (Siphonaptera: Pulicidae) from several regions of the United States.
2002 Sep
Suppression of bloodfeeding by Ochlerotatus dorsalis and Ochlerotatus melanimon on cattle treated with python ear tags.
2002 Sep
Synergized bifenthrin plus chlorpyrifos-methyl for control of beetles and psocids in sorghum in Australia.
2003 Apr
Action of pyrethrum-based formulations against grain weevils.
2003 Apr 30
Isocratic reversed-phase liquid chromatographic method for the simultaneous determination of (S)-methoprene, MGK264, piperonyl butoxide, sumithrin and permethrin in pesticide formulation.
2003 Jan 3
Efficacy and tolerability of natural synergised pyrethrins in a new thermo labile foam formulation in topical treatment of scabies: a prospective, randomised, investigator-blinded, comparative trial vs. permethrin cream.
2003 Jan-Feb
Resistance to coumaphos and diazinon in Boophilus microplus (Acari: Ixodidae) and evidence for the involvement of an oxidative detoxification mechanism.
2003 Jul
Analysis of protein induction in the CNS of SJL mice with experimental allergic encephalomyelitis by proteomic screening and immunohistochemistry.
2003 Jul
Biotransformation and bioconcentration of pyrene in Daphnia magna.
2003 Jun 19
Mechanisms of resistance to DDT and pyrethroids in Patagonian populations of Simulium blackflies.
2003 Mar
Reproductive and neurobehavioural effects of piperonyl butoxide administered to mice in the diet.
2003 Mar
Direct on-line continuous supercritical fluid extraction and HPLC of aqueous pyrethrins solutions.
2003 Mar 15
Biodegradation of chloronaphthalenes and polycyclic aromatic hydrocarbons by the white-rot fungus Phlebia lindtneri.
2003 May
Bioconcentration and acute toxicity of polycyclic musks in two benthic organisms (Chironomus riparius and Lumbriculus variegatus).
2003 May
Oxidative stress in laboratory-incubated double-crested cormorant eggs collected from the Great Lakes.
2003 Nov
Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil.
2003 Nov 19
Effect of horn fly and internal parasite control on growth of beef heifers.
2003 Nov 28
Ecotoxicologic impacts of agricultural drain water in the Salinas River, California, USA.
2003 Oct
Phthalates, alkylphenols, pesticides, polybrominated diphenyl ethers, and other endocrine-disrupting compounds in indoor air and dust.
2003 Oct 15
Optimizing an aerial spray for mosquito control.
2003 Sep
Mechanisms of TCDD-induced abnormalities and embryo lethality in white leghorn chickens.
2003 Sep
Oxidative stress in liver and brain of the hatchling chicken (Gallus domesticus) following in ovo injection with TCDD.
2003 Sep
Pyrethroid tolerance in Culex pipiens pipiens var molestus from Marin County, California.
2004 Apr
The involvement of microsomal oxidases in pyrethroid resistance in Helicoverpa armigera from Asia.
2004 Aug
Teratogenesis in Fundulus heteroclitus embryos exposed to a creosote-contaminated sediment extract and CYP1A inhibitors.
2004 Aug-Dec
Responses of Corcyra cephalonica (Stainton) to pirimiphos-methyl, spinosad, and combinations of pirimiphos-methyl and synergized pyrethrins.
2004 Feb
Role of piperonyl butoxide in the toxicity of chlorpyrifos to Ceriodaphnia dubia and Xenopus laevis.
2004 Feb
Pyrethrins and piperonyl butoxide adsorption to soil organic matter.
2004 Jan
Toxaphene detoxification and acclimation in Daphnia magna: do cytochrome P-450 enzymes play a role?
2004 Jan
Frequency of kdr gene in house fly field populations: correlation of pyrethroid resistance and kdr frequency.
2004 Jun
Diagnostic dose of synergized d-phenothrin for insecticide susceptibility testing by bottle bioassay.
2004 Jun
Development of a novel self-medicating applicator for control of internal and external parasites of wild and domestic animals.
2004 Mar
Detection and characterization of amitraz resistance in the southern cattle tick, Boophilus microplus (Acari: Ixodidae).
2004 Mar
Videodermatoscopy enhances the ability to monitor efficacy of scabies treatment and allows optimal timing of drug application.
2004 Mar
Synergism of insecticides provides evidence of metabolic mechanisms of resistance in the obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae).
2004 May
Preliminary evidence of the role of hydrogen peroxide in the degradation of benzo[a]pyrene by a non-white rot fungus Fusarium solani.
2004 May
Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives.
2004 May 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
S-bioallethrin and PIPERONYL BUTOXIDE (PBO) caused inhibition of lymphocyte proliferation (MTT-test) after a 72-h culture period in a concentration dependent manner.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:21:11 UTC 2023
Edited
by admin
on Fri Dec 15 15:21:11 UTC 2023
Record UNII
LWK91TU9AH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPERONYL BUTOXIDE
GREEN BOOK   HSDB   INCI   ISO   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INCI  
Official Name English
Piperonyl butoxide [WHO-DD]
Common Name English
PIPERONYL BUTOXIDE [VANDF]
Common Name English
PIPERONYL BUTOXIDE [MI]
Common Name English
PIPERONYL BUTOXIDE TECHNICAL [VANDF]
Common Name English
PIPERONYL BUTOXIDE COMPONENT OF RID MOUSSE
Common Name English
PIPERONYL BUTOXIDE [GREEN BOOK]
Common Name English
PIPERONYL BUTOXIDE [INCI]
Common Name English
PIPERONYL BUTOXIDE [ORANGE BOOK]
Common Name English
PIPERONYL BUTOXIDE [MART.]
Common Name English
RID MOUSSE COMPONENT PIPERONYL BUTOXIDE
Common Name English
PIPERONYL BUTOXIDE [ISO]
Common Name English
PIPERONYL BUTOXIDE [IARC]
Common Name English
NSC-8401
Code English
PIPERONYL BUTOXIDE TECHNICAL
VANDF  
Common Name English
1,3-BENZODIOXOLE, 5-((2-(2-BUTOXYETHOXY)ETHOXY)METHYL)-6-PROPYL
Common Name English
5((2-(2-BUTOXYETHOXY)ETHOXY)METHYL)-6-PROPYL-1,3-BENZODIOXOLE
Systematic Name English
PIPERONYL BUTOXIDE [HSDB]
Common Name English
5-((2-(2-BUTOXYETHOXY)ETHOXY)METHYL)-6-PROPYL-1,3-BENZODIOXOLE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C45187
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
CFR 21 CFR 358.610
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
EPA PESTICIDE CODE 67501
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
IARC Piperonyl butoxide
Code System Code Type Description
FDA UNII
LWK91TU9AH
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
MESH
D010882
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
HSDB
1755
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201131
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
EVMPD
SUB14893MIG
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
DAILYMED
LWK91TU9AH
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
CAS
51-03-6
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
RXCUI
8345
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY RxNorm
SMS_ID
100000091753
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
NSC
8401
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID1021166
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-076-7
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
DRUG BANK
DB09350
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
MERCK INDEX
m8859
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C29849
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
WIKIPEDIA
PIPERONYL BUTOXIDE
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
DRUG CENTRAL
4276
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
ALANWOOD
piperonyl butoxide
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
PUBCHEM
5794
Created by admin on Fri Dec 15 15:21:11 UTC 2023 , Edited by admin on Fri Dec 15 15:21:11 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY