PYRIPROXYFEN

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H19NO3
Molecular Weight	321.3698
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(COC1=CC=C(OC2=CC=CC=C2)C=C1)OC3=NC=CC=C3

InChI

InChIKey=NHDHVHZZCFYRSB-UHFFFAOYSA-N

InChI=1S/C20H19NO3/c1-16(23-20-9-5-6-14-21-20)15-22-17-10-12-19(13-11-17)24-18-7-3-2-4-8-18/h2-14,16H,15H2,1H3

HIDE SMILES / InChI

Molecular Formula	C20H19NO3
Molecular Weight	321.3698
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://onlinelibrary.wiley.com/doi/10.1002/ps.2780430308/abstract | http://www.who.int/water_sanitation_health/dwq/chemicals/Pyriproxyfensum.pdf | http://heavy.com/news/2016/02/pyriproxyfen-microcephaly-products-larvicide-zika-birth-defects-in-drinking-water-pet-flea-tick-treatments-piriproxifen/

Pyriproxyfen is a broad-spectrum insect growth regulator with insecticidal activity against public health insect pests: houseflies, mosquitoes and cockroaches. In agriculture and horticulture, pyriproxyfen has registered uses for the control of scale, whitefly, bollworm, jassids, aphids and cutworms. Pyriproxyfen is used on citrus fruit in Israel, South Africa, Spain and Italy. Pyriproxyfen is one of several insecticides used for the control of the red imported fire ant (Solenopsis invicta) in California, USA. Pyriproxyfen has also been considered by WHO for vector control under its Pesticides Evaluation Scheme. It is a potent suppressor of embryogenesis and adult formation of the sweetpotato whitefly, Bemisia tabaci (Gennadius), and the greenhouse whitefly, Trialeurodes vaporariorum (Westwood). Dipping of cotton or tomato seedlings infested with 0 to 1-day-old eggs in 0.1 mg litre−1 resulted in over 90% suppression of egg hatch of both B. tabaci and T. vaporariorum. Pyriproxyfen is registered in the U.S. for flea and tick control in the home and on pets, as well as indoor and outdoor ant and roach control. Formulas include carpet powders, foggers, aerosols, shampoos, bait, and pet collars.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phenoloxidase, Ephestia kuehniella 1 Target ID: Phenoloxidase, Ephestia kuehniella Sources: https://www.ncbi.nlm.nih.gov/pubmed/25373499	Inhibitor 8504
juvenile hormone metabolic process 1 Target ID: GO:0006716 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18485359 \| https://www.ncbi.nlm.nih.gov/pubmed/12770247	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ectoparasitic infestations 3 Sources: http://www.ekavet.com/veterinary-medications/1396-pyriproxyfen-1-premix-for-dog-virbac https://www.drugs.com/international/pyriproxyfen.html	Preventing		Approved 8583	Pyriproxyfen Virbac Approved Use Ectoparasiticide, Prevention of flea multiplication by sterilising the eggs

C_max

Value	Dose	Co-administered	Analyte	Population
21.5 ng/mL OTHER GOV'T https://www.vmd.defra.gov.uk/productinformationdatabase/files/SPC_Documents/SPC_153104.PDF	500 μg/kg single, oral dose: 500 μg/kg route of administration: Oral experiment type: SINGLE co-administered:		PYRIPROXYFEN plasma	Canis lupus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
145.2 ng × h/mL OTHER GOV'T https://www.vmd.defra.gov.uk/productinformationdatabase/files/SPC_Documents/SPC_153104.PDF	500 μg/kg single, oral dose: 500 μg/kg route of administration: Oral experiment type: SINGLE co-administered:		PYRIPROXYFEN plasma	Canis lupus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
10 h OTHER GOV'T https://www.vmd.defra.gov.uk/productinformationdatabase/files/SPC_Documents/SPC_153104.PDF	500 μg/kg single, oral dose: 500 μg/kg route of administration: Oral experiment type: SINGLE co-administered:		PYRIPROXYFEN plasma	Canis lupus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP19A1 429 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91753#section=Biological-Test-Results Page: 11.0	no [IC50 35.5742 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91753#section=Biological-Test-Results Page: 11.0	no [IC50 38.5316 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91753#section=Biological-Test-Results Page: 73.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91753#section=Biological-Test-Results Page: 2.0	yes [IC50 10.0262 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91753#section=Biological-Test-Results Page: 5.0	yes [IC50 15.8904 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91753#section=Biological-Test-Results Page: 5.0	yes [IC50 15.8904 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91753#section=Biological-Test-Results Page: 7.0

PubMed

Title	Date	PubMed
Cloning and characterization of the retinoid X receptor from a primitive crustacean Daphnia magna.	2007-01-15	17005181
Atrazine stimulates hemoglobin accumulation in Daphnia magna: is it hormonal or hypoxic?	2006-10	16854968
Effects of the juvenile hormone analog pyriproxyfen on German cockroach, Blattella germanica (L.), tergal gland development and production of tergal gland secretion proteins.	2006-09	16921520
Evaluation of the estrogenic activities of some pesticides and their combinations using MtT/Se cell proliferation assay.	2006-09	16781191
Evaluation of a spray of permethrin and pyriproxyfen for the protection of dogs against Phlebotomus perniciosus.	2006-08-12	16905734
Bumblebees can be used in combination with juvenile hormone analogues and ecdysone agonists.	2006-08	16988884
Modeling evolution of resistance to pyriproxyfen by the sweetpotato whitefly (Homoptera: Aleyrodidae).	2006-08	16937698
The antifouling activity of some juvenoids on three species of acorn barnacle, Balanus.	2006-07	16705617
Susceptibility of adult Coccinella septempunctata (Coleoptera: Coccinellidae) to insecticides with different modes of action.	2006-07	16649191
Organization and repression by juvenile hormone of a vitellogenin gene cluster in the crustacean, Daphnia magna.	2006-06-23	16681994
Juvenile hormone is required to couple imaginal disc formation with nutrition in insects.	2006-06-02	16741122
Role of two insect growth regulators in integrated pest management of citrus scales.	2006-06	16813306
Genetic differences in the production of male neonates in Daphnia magna exposed to juvenile hormone analogs.	2006-06	16289230
Effective control of dengue vectors with curtains and water container covers treated with insecticide in Mexico and Venezuela: cluster randomised trials.	2006-05-27	16735334
Laboratory evaluation of pyriproxifen treated bednets on mosquito fertility and fecundity. A preliminary study.	2006-05-26	16722354
A candidate juvenoid hormone receptor cis-element in the Daphnia magna hb2 hemoglobin gene promoter.	2006-03-09	16406259
Inhibition of adult emergence of Aedes aegypti in simulated domestic water-storage containers by using a controlled-release formulation of pyriproxyfen.	2006-03	16646342
[Persistence and efficacy of growth regulator pyriproxyfen in laboratory conditions for Aedes aegypti].	2006-02-28	16501771
Effect of Bacillus thuringiensis subsp. israelensis and neonicotinoid insecticides on the fungus gnat Bradysia sp nr. coprophila (Lintner) (Diptera: Sciaridae).	2006-02	16408320
Evaluation of novel insecticides for control of dengue vector Aedes aegypti (Diptera: Culicidae).	2006-01	16506447
20-Hydroxyecdysone and juvenile hormone regulate the laminarin-induced nodulation reaction in larvae of the flesh fly, Neobellieria bullata.	2006	16336999
Effects of juvenile hormone analogs on new reproductives and colony growth of Pharaoh ant (Hymenoptera: Formicidae).	2005-12	16539147
Development, oviposition, and mortality of Neoseiulus fallacis (Acari: Phytoseiidae) in response to reduced-risk insecticides.	2005-12	16539140
Sensitivity of the larvivorous copepod species, Mesocyclops pehpeiensis and Megacyclops viridis, to the insect growth regulator, pyriproxyfen.	2005-12	16506581
DNA markers for identifying biotypes B and Q of Bemisia tabaci (Hemiptera: Aleyrodidae) and studying population dynamics.	2005-12	16336708
Evaluation of the efficacy of dill apiol and pyriproxyfen in the treatment and control of Xenopsylla cheopis flea Roths (Siphonaptera: Pulicidae).	2005-12	16333908
Evidence of detrimental effects of environmental contaminants on growth and reproductive physiology of white sturgeon in impounded areas of the Columbia River.	2005-12	16330346
Routine application using single quadrupole liquid chromatography-mass spectrometry to pesticides analysis in citrus fruits.	2005-09-23	16130755
The role of nutrition in creation of the eye imaginal disc and initiation of metamorphosis in Manduca sexta.	2005-09-15	16099447
The screening of chemicals for juvenoid-related endocrine activity using the water flea Daphnia magna.	2005-09-10	16046008
Laboratory and field evaluation of the insect growth regulator pyriproxyfen (Sumilarv 0.5G) against dengue vectors.	2005-09	16252520
Evaluation of estrogenic activities of pesticides using an in vitro reporter gene assay.	2005-08	16175743
Vitellogenin expression in queen ovaries and in larvae of both sexes of Apis mellifera.	2005-08	16034983
Potential use of pyriproxyfen for control of Aedes aegypti (Diptera: Culicidae) in Iquitos, Perú.	2005-07	16119551
Tomato metabolism and porphyrin-catalyzed oxidation of pyriproxyfen.	2005-06-29	15969518
Residual activity and population effects of noviflumuron for German cockroach (Dictyoptera: Blattellidae) control.	2005-06	16022319
Conservation of natural enemies in cotton: comparative selectivity of acetamiprid in the management of Bemisia tabaci.	2005-06	15712368
Capillary electrophoresis for analyzing pesticides in fruits and vegetables using solid-phase extraction and stir-bar sorptive extraction.	2005-05-06	15909524
Biotypes B and Q of Bemisia tabaci and their relevance to neonicotinoid and pyriproxyfen resistance.	2005-04	15756703
Biorational insecticides: mechanism and cross-resistance.	2005-04	15756702
Comparison of liquid chromatography using triple quadrupole and quadrupole ion trap mass analyzers to determine pesticide residues in oranges.	2005-03-04	15844516
Integration of Bacillus thuringiensis H-14 formulations and pyriproxyfen for the control of larvae of Aedes aegypti and Aedes albopictus.	2005-03	15825767
Efficacy of a collar impregnated with amitraz and pyriproxyfen for prevention of experimental tick infestations by Rhipicephalus sanguineus, Ixodes ricinus, and Ixodes scapularis in dogs.	2005-01-15	15706971
Habitat characterization and spatial distribution of Anopheles sp. mosquito larvae in Dar es Salaam (Tanzania) during an extended dry period.	2005-01-14	15649333
Role of neonicotinyl insecticides in Washington apple integrated pest management. Part I. Control of lepidopteran pests.	2005	16341246
Control of chironomid midge larvae in wastewater stabilisation ponds: comparison of five compounds.	2005	16114682
Control of vectors and incidence of malaria in an irrigated settlement scheme in Sri Lanka by using the insect growth regulator pyriproxyfen.	2004-12	15669380
The multicolored Asian lady beetle, Harmonia axyridis: a review of its biology, uses in biological control, and non-target impacts.	2003	15841248
Structure-based analysis of the ultraspiracle protein and docking studies of putative ligands.	2002	15455059
Effects of juvenile hormone and ecdysone on the timing of vitellogenin appearance in hemolymph of queen and worker pupae of Apis mellifera.	2002	15455035

Patents

Sample Use Guides

In Vivo Use Guide

Rats: single oral dose of [phenyl-14C]pyriproxyfen to rats at 2 mg/kg bw (low dose) and 1000 mg/kg bw (high dose). Rats were also dosed orally with unlabelledpyriproxyfen at 2 mg/kg bw/day for 14 consecutive days followed by a single oral dose of labelledpyriproxyfen at the same rate.

Route of Administration: Oral

In Vitro Use Guide

Pyriproxyfen in vitro inhibited the phenoloxidase extracted and purified from hemocytes of Ephestia kuehniella with IC50 of 38.59 ug/ml

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:33:49 GMT 2025` Edited by `admin` on `Mon Mar 31 21:33:49 GMT 2025`
Record UNII	3Q9VOR705O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRIPROXYFEN

Common Name

English

ADMIRAL

Preferred Name

English

S-9318

Code

English

VECTRA 3D COMPONENT PYRIPROXYFEN

Brand Name

English

4-PHENOXYPHENYL (RS)-2-(2-PYRIDYLOXY)PROPYL ETHER

Systematic Name

English

SUMILARV

Brand Name

English

PYRIPROXYFEN [MI]

Common Name

English

JUVENTOX

Brand Name

English

TIGER

Brand Name

English

SEIZE

Brand Name

English

S-71639

Code

English

PYRIPROXYFEN, (±)-

Common Name

English

(±)-PYRIPROXYFEN

Common Name

English

VECTRA FELIS COMPONENT PYRIPROXYFEN

Brand Name

English

PYRIPROXYFEN [MART.]

Common Name

English

DISTANCE

Brand Name

English

PLUTO MC

Brand Name

English

PYRIPROXYFEN [EMA EPAR VETERINARY]

Common Name

English

ESTEEM

Brand Name

English

2-(1-METHYL-2-(4-PHENOXYPHENOXY)ETHOXY)PYRIDINE

Systematic Name

English

PYRIPROXYFEN [JAN]

Common Name

English

NYLAR

Brand Name

English

PYRIDINE, 2-(1-METHYL-2-(4-PHENOXYPHENOXY)ETHOXY)-

Systematic Name

English

JUVINAL

Brand Name

English

PYRIPROXYFEN [ISO]

Common Name

English

SK-591

Code

English

CYCLIO

Brand Name

English

OMS-3019

Code

English

ARCHER IGR

Brand Name

English

NYGUARD IGR

Brand Name

English

LANO TAPE

Brand Name

English

NEMESIS

Brand Name

English

KNACK

Brand Name

English

S-31183

Code

English

BCP-8702

Code

English

Classification Tree Code System Code

EMA VETERINARY ASSESSMENT REPORTS

VECTRA 3D [AUTHORIZED]