CYROMAZINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10N6
Molecular Weight	166.1838
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(NC2CC2)=NC(N)=N1

InChI

InChIKey=LVQDKIWDGQRHTE-UHFFFAOYSA-N

InChI=1S/C6H10N6/c7-4-10-5(8)12-6(11-4)9-3-1-2-3/h3H,1-2H2,(H5,7,8,9,10,11,12)

HIDE SMILES / InChI

Molecular Formula	C6H10N6
Molecular Weight	166.1838
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11093244 | http://pmep.cce.cornell.edu/profiles/insect-mite/cadusafos-cyromazine/cyromazine/insect-prof-cyromazine.html | http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500013079.pdf

Cyromazine, an insect growth regulator, affects larval and pupal cuticles in dipterans and some other insects. The mode of action of this aminotriazine is not known yet, though it has been shown not to inhibit the synthesis of chitin and cuticular proteins. Cyromazine may, however, act on some step(s) of sclerotization of the cuticle. Cyromazine is not a cholinesterase inhibitor. As an insect growth regulator, cyrozine exerts its toxic action by affecting the nervous system of the immature stages (larvae) of certain insects.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cutaneous myiasis of sheep 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2316158 https://www.ncbi.nlm.nih.gov/pubmed/1759337	Preventing		Approved 8583	Cyromazine Spray-On Approved Use For the prevention of blowfly strike on sheep

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2E1 1060 CYP19A1 429 CYP2A6 879 CYP2C19 2057 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47866#section=BioAssay-Results Page: 7.0	inconclusive [IC50 38.9018 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47866#section=BioAssay-Results Page: 7.0	inconclusive [IC50 61.6448 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47866#section=BioAssay-Results Page: 3.0	no [IC50 8.709 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMzExMDcifX0=	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47866#section=BioAssay-Results Page: 81.0	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47866#section=BioAssay-Results Page: 74.0	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMzExMDcifX0=	no [IC50 >10 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47866#section=BioAssay-Results Page: 149.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47866#section=BioAssay-Results Page: 235.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIzMTEwNyJ9fQ==

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Development of a high performance liquid chromatography method and a liquid chromatography-tandem mass spectrometry method with pressurized liquid extraction for simultaneous quantification and confirmation of cyromazine, melamine and its metabolites in foods of animal origin.	2010-12-03	21056714
Putative polymerase chain reaction markers for insecticide resistance in the leafminer Liriomyza trifolii (Diptera: Agromyzidae) to cyromazine and abamectin.	2010-12	21309244
High-resolution structures of Trypanosoma brucei pteridine reductase ligand complexes inform on the placement of new molecular entities in the active site of a potential drug target.	2010-12	21123874
Association of poultry farms with housefly and morbidity: a comparative study from raipur rani, haryana.	2010-10	21278864
Molecularly-imprinted microspheres for selective extraction and determination of melamine in milk and feed using gas chromatography-mass spectrometry.	2010-09-01	20674520
Effective separation and simultaneous detection of cyromazine and melamine in food by capillary electrophoresis.	2010-07	20593399
First report of cyromazine resistance in a population of UK house fly (Musca domestica) associated with intensive livestock production.	2010-07	20533379
Analysis of cyromazine in poultry feed using the QuEChERS method coupled with LC-MS/MS.	2010-05-26	20155910
Hapten synthesis and antibody production for the development of a melamine immunoassay.	2010-04-14	20381695
Melamine acoustic chemosensor based on molecularly imprinted polymer film.	2009-12-15	19925007
Determination of residues of cyromazine and its metabolite, melamine, in animal-derived food by gas chromatography-mass spectrometry with derivatization.	2009-12-09	19899757
Interaction between Beauveria bassiana and Bacillus thuringiensis var. israelensis for the control of house fly larvae and adults in poultry houses.	2009-11	19834080
[Adsorption of cyromazine on five typical soils in China].	2009-10-15	19968133
Lignin-based formulations to prevent pesticides pollution.	2009-08-30	19272698
Novel cyromazine imprinted polymer applied to the solid-phase extraction of melamine from feed and milk samples.	2009-08-21	19631323
High-performance liquid chromatographic method for the determination of cyromazine and melamine residues in milk and pork.	2009-08	19772731
Insecticide resistance of house fly, Musca domestica (L.) from Argentina.	2009-08	19340457
[Determination of residues of cyromazine and its metabolite melamine in chickens by gas chromatography-mass spectrometry].	2009-07	19938492
Toxicological risk of melamine and cyanuric acid in food and feed.	2009-06	21217848
Multiresidue pesticide analysis of wines by dispersive solid-phase extraction and ultrahigh-performance liquid chromatography-tandem mass spectrometry.	2009-05-27	19371141
Analytical method for simultaneous determination of pesticide and veterinary drug residues in milk by CE-MS.	2009-05	19384986
Effect of compost and casing treatments of insecticides against the sciarid Bradysia ocellaris (Diptera: Sciaridae) and on the total yield of cultivated mushrooms, Agaricus bisporus.	2009-04	19172599
Sheep blowfly strike risk and management in Great Britain: a survey of current practice.	2008-12	19120956
Simultaneous determination of seven pesticides in waters using multi-walled carbon nanotube SPE and NACE.	2008-11	18956435
Laboratory evaluation of cyromazine against insecticide-susceptible and -resistant mosquito larvae.	2008-03	18437826
Application and fate of Cyromazine in a closed-cycle hydroponic cultivation of bean (Phaseolus vulgaris L.).	2007-11-28	17979234
Modification and re-validation of the ethyl acetate-based multi-residue method for pesticides in produce.	2007-11	17563885
Controlled-release formulations of cyromazine-lignin matrix coated with ethylcellulose.	2007-09-01	17763045
Controlled release systems to prevent the agro-environmental pollution derived from pesticide use.	2007-09-01	17763044
Laboratory evaluation of five chitin synthesis inhibitors against the colorado potato beetle, Leptinotarsa decemlineata.	2007	20345285
Controlled release of isoproturon, imidacloprid, and cyromazine from alginate-bentonite-activated carbon formulations.	2006-12-27	17177541
The insect growth regulator insecticide cyromazine causes earlier emergence in Drosophila melanogaster.	2006-11	17048245
Hazards and uptake of chitin synthesis inhibitors in bumblebees Bombus terrestris.	2006-08	16786494
Positional cloning of a cyromazine resistance gene in Drosophila melanogaster.	2006-04	16640728
Juvenile and sublethal effects of selected pesticides on the leafminer parasitoids Hemiptarsenus varicornis and Diglyphus isaea (Hymenoptera: Eulophidae) from Australia.	2005-12	16539101
Studies of the intermediary metabolism in cultured cells of the insect Spodoptera frugiperda using 13C- or 15N-labelled tracers.	2005-11-14	16285881
Combining solid-phase microextraction and on-line preconcentration-capillary electrophoresis for sensitive analysis of pesticides in foods.	2005-02	15714540
Effects of two plant extracts on larval leafminer Liriomyza trifolii (Diptera: Agromyzidae) in tomatoes.	2004-10	15568346
Toxicity of chemicals commonly used in Indonesian vegetable crops to Liriomyza huidobrensis populations and the Indonesian parasitoids Hemiptarsenus varicornis, Opius sp., and Gronotoma micromorpha, as well as the Australian parasitoids Hemiptarsenus varicornis and Diglyphus isaea.	2004-08	15384326
Highly sensitive analysis of multiple pesticides in foods combining solid-phase microextraction, capillary electrophoresis-mass spectrometry, and chemometrics.	2004-07	15237407
Determination of poultry feed-through insecticide activity in an in vivo anticoccidial assay.	2004-04	15165074
Development and stability of insecticide resistance in the leafminer Liriomyza trifolii (Diptera: Agromyzidae) to cyromazine, abamectin, and spinosad.	2004-02	14998134
Cyromazine seed treatments to control onion maggot, Delia antiqua, on green onions.	2003-10	14650523
Controlled-release systems for the delivery of cyromazine into water surface.	2003-09-24	13129304
Larvicide resistance in Musca domestica (Diptera: Muscidae) populations in Denmark and establishment of resistant laboratory strains.	2003-08	14503604
Genetics and fitness costs of cyromazine resistance in the house fly (Diptera: Muscidae).	2002-12	12539839
Impact of an insecticide resistance strategy for house fly (Diptera: Muscidae) control in intensive animal units in the United Kingdom.	2002-12	12539838
Cabbage root fly control using non-organophosphorus insecticides.	2001	12425060
Bacterial degradation of N-cyclopropylmelamine. The steps to ring cleavage.	1984-09-01	6477516

Patents

Sample Use Guides

In Vivo Use Guide

In a series of 4 trials, dairy calves housed in outdoor hutches were administered technical cyromazine daily at rates of 0, 0.1, 0.5, and 1.0 mg/kg body weight.

Route of Administration: Oral

In Vitro Use Guide

There was no significant inhibition of dihydrofolate reductase (DHFR) from larvae of the blowfly, Protophormia terraenovae, and from hen liver at 100 uM by cyromazine.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:05 GMT 2025`
Record UNII	CA49Y29RA9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYROMAZINE

Official Name

English

NEPOREX

Preferred Name

English

CYROMAZINE [USP IMPURITY]

Common Name

English

CYROMAZINE [HSDB]

Common Name

English

CGA-72662

Code

English

N-CYCLOPROPYL-1,3,5-TRIAZINE-2,4,6-TRIAMINE

Systematic Name

English

2-Cyclopropylamino-4,6-diamino-S-triazine

Systematic Name

English

CGA 72662

Code

English

cyromazine [INN]

Common Name

English

CYROMAZINE [MI]

Common Name

English

CYROMAZINE [ISO]

Common Name

English

CYROMAZINE [USP-RS]

Common Name

English

NSC-759268

Code

English

CYROMAZINE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C737