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
SMILES
CCCCOCCOCCOCC1=C(CCC)C=C2OCOC2=C1
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
| 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
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17162471/ |
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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator​
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 69.4275 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/8794879/ |
no | |||
| yes [IC50 0.0453 uM] | ||||
| yes [IC50 0.123 uM] | ||||
| yes [IC50 0.286 uM] | ||||
| yes [IC50 0.3209 uM] | ||||
| yes [IC50 0.6404 uM] | ||||
| yes [IC50 <10 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/8794879/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8794879/ |
yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| The involvement of microsomal oxidases in pyrethroid resistance in Helicoverpa armigera from Asia. | 2004-08 |
|
| Teratogenesis in Fundulus heteroclitus embryos exposed to a creosote-contaminated sediment extract and CYP1A inhibitors. | 2004-06-05 |
|
| Frequency of kdr gene in house fly field populations: correlation of pyrethroid resistance and kdr frequency. | 2004-06 |
|
| Diagnostic dose of synergized d-phenothrin for insecticide susceptibility testing by bottle bioassay. | 2004-06 |
|
| Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives. | 2004-05-15 |
|
| Synergism of insecticides provides evidence of metabolic mechanisms of resistance in the obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae). | 2004-05 |
|
| Preliminary evidence of the role of hydrogen peroxide in the degradation of benzo[a]pyrene by a non-white rot fungus Fusarium solani. | 2004-05 |
|
| Pyrethroid tolerance in Culex pipiens pipiens var molestus from Marin County, California. | 2004-04 |
|
| Development of a novel self-medicating applicator for control of internal and external parasites of wild and domestic animals. | 2004-03 |
|
| Detection and characterization of amitraz resistance in the southern cattle tick, Boophilus microplus (Acari: Ixodidae). | 2004-03 |
|
| Videodermatoscopy enhances the ability to monitor efficacy of scabies treatment and allows optimal timing of drug application. | 2004-03 |
|
| Responses of Corcyra cephalonica (Stainton) to pirimiphos-methyl, spinosad, and combinations of pirimiphos-methyl and synergized pyrethrins. | 2004-02 |
|
| Role of piperonyl butoxide in the toxicity of chlorpyrifos to Ceriodaphnia dubia and Xenopus laevis. | 2004-02 |
|
| Pyrethrins and piperonyl butoxide adsorption to soil organic matter. | 2004-01 |
|
| Toxaphene detoxification and acclimation in Daphnia magna: do cytochrome P-450 enzymes play a role? | 2004-01 |
|
| Effect of horn fly and internal parasite control on growth of beef heifers. | 2003-11-28 |
|
| Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil. | 2003-11-19 |
|
| Oxidative stress in laboratory-incubated double-crested cormorant eggs collected from the Great Lakes. | 2003-11 |
|
| Phthalates, alkylphenols, pesticides, polybrominated diphenyl ethers, and other endocrine-disrupting compounds in indoor air and dust. | 2003-10-15 |
|
| Ecotoxicologic impacts of agricultural drain water in the Salinas River, California, USA. | 2003-10 |
|
| Optimizing an aerial spray for mosquito control. | 2003-09 |
|
| Mechanisms of TCDD-induced abnormalities and embryo lethality in white leghorn chickens. | 2003-09 |
|
| Oxidative stress in liver and brain of the hatchling chicken (Gallus domesticus) following in ovo injection with TCDD. | 2003-09 |
|
| Resistance to coumaphos and diazinon in Boophilus microplus (Acari: Ixodidae) and evidence for the involvement of an oxidative detoxification mechanism. | 2003-07 |
|
| Analysis of protein induction in the CNS of SJL mice with experimental allergic encephalomyelitis by proteomic screening and immunohistochemistry. | 2003-07 |
|
| Biotransformation and bioconcentration of pyrene in Daphnia magna. | 2003-06-19 |
|
| Biodegradation of chloronaphthalenes and polycyclic aromatic hydrocarbons by the white-rot fungus Phlebia lindtneri. | 2003-05 |
|
| Bioconcentration and acute toxicity of polycyclic musks in two benthic organisms (Chironomus riparius and Lumbriculus variegatus). | 2003-05 |
|
| Action of pyrethrum-based formulations against grain weevils. | 2003-04-30 |
|
| Synergized bifenthrin plus chlorpyrifos-methyl for control of beetles and psocids in sorghum in Australia. | 2003-04 |
|
| Direct on-line continuous supercritical fluid extraction and HPLC of aqueous pyrethrins solutions. | 2003-03-15 |
|
| 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. | 2003-03-01 |
|
| Mechanisms of resistance to DDT and pyrethroids in Patagonian populations of Simulium blackflies. | 2003-03 |
|
| Reproductive and neurobehavioural effects of piperonyl butoxide administered to mice in the diet. | 2003-03 |
|
| Isocratic reversed-phase liquid chromatographic method for the simultaneous determination of (S)-methoprene, MGK264, piperonyl butoxide, sumithrin and permethrin in pesticide formulation. | 2003-01-03 |
|
| Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals. | 2002-12 |
|
| Efficacy of ethiprole applied alone and in combination with conventional insecticides for protection of stored wheat and stored corn. | 2002-12 |
|
| Impact of an insecticide resistance strategy for house fly (Diptera: Muscidae) control in intensive animal units in the United Kingdom. | 2002-12 |
|
| Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products. | 2002-12 |
|
| Fenbendazole pharmacokinetics, metabolism, and potentiation in horses. | 2002-11 |
|
| Scabies and pediculosis pubis: an update of treatment regimens and general review. | 2002-10-15 |
|
| Effects of iprodione and fludioxonil on glycerol synthesis and hyphal development in Candida albicans. | 2002-10 |
|
| Near UV quantum yields for rotenone and piperonyl butoxide. | 2002-10 |
|
| Efficacy of the organic-certified insecticide Diatect II against the boll weevil (Anthonomus grandis) in cotton. | 2002-10 |
|
| The in vivo pediculicidal efficacy of a natural remedy. | 2002-10 |
|
| Oxidation of dibenzo- p-dioxin, dibenzofuran, biphenyl, and diphenyl ether by the white-rot fungus Phlebia lindtneri. | 2002-10 |
|
| Insecticide susceptibilities of cat fleas (Siphonaptera: Pulicidae) from several regions of the United States. | 2002-09 |
|
| Suppression of bloodfeeding by Ochlerotatus dorsalis and Ochlerotatus melanimon on cattle treated with python ear tags. | 2002-09 |
|
| 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 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10414782
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
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admin
on
Edited
Mon Mar 31 17:54:58 GMT 2025
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on
Mon Mar 31 17:54:58 GMT 2025
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| Record UNII |
LWK91TU9AH
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C45187
Created by
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CFR |
21 CFR 358.610
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EPA PESTICIDE CODE |
67501
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IARC | Piperonyl butoxide |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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LWK91TU9AH
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D010882
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1755
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CHEMBL1201131
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SUB14893MIG
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LWK91TU9AH
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51-03-6
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8345
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100000091753
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8401
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DTXSID1021166
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200-076-7
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DB09350
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m8859
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PRIMARY | Merck Index | ||
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C29849
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PIPERONYL BUTOXIDE
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4276
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piperonyl butoxide
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5794
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