Cyromazine
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Basic Info
| Common Name | Cyromazine(F05404) |
| 2D Structure | |
| Description | Ectoparasiticide. Insect growth regulator. Specific activity against dipterous larvae. Cyromazine is a fda approved for use in livestock. Cyromazine belongs to the family of Aminotriazines. These are organic compounds containing an amino group attached to a triazine ring. |
| FRCD ID | F05404 |
| CAS Number | 66215-27-8 |
| PubChem CID | 47866 |
| Formula | C6H10N6 |
| IUPAC Name | 2-N-cyclopropyl-1,3,5-triazine-2,4,6-triamine |
| InChI Key | LVQDKIWDGQRHTE-UHFFFAOYSA-N |
| InChI | 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) |
| Canonical SMILES | C1CC1NC2=NC(=NC(=N2)N)N |
| Isomeric SMILES | C1CC1NC2=NC(=NC(=N2)N)N |
| Synonyms |
Citation
CYROMAZINE
66215-27-8
Larvadex
Vetrazin
Trigard
Cyclopropylmelamine
Vetrazine
Neporex
Cypromazine
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazines |
| Subclass | Aminotriazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | N-aliphatic s-triazines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | N-aliphatic s-triazine - Secondary aliphatic/aromatic amine - 1,3,5-triazine - Heteroaromatic compound - Azacycle - Secondary amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as n-aliphatic s-triazines. These are n-aliphatic amine derivatives of 1,3,5-triazines. 1,3,5-triazines are aromatic compounds having three nitrogen ring atoms at the 1-, 3-, and 5- positions. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 166.188 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 2 |
| Complexity | 148 |
| Monoisotopic Mass | 166.097 |
| Exact Mass | 166.097 |
| XLogP | -0.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8531 |
| Human Intestinal Absorption | HIA+ | 0.9779 |
| Caco-2 Permeability | Caco2+ | 0.5842 |
| P-glycoprotein Substrate | Non-substrate | 0.6831 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9768 |
| Non-inhibitor | 0.9890 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7770 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6883 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8896 |
| CYP450 2D6 Substrate | Non-substrate | 0.7970 |
| CYP450 3A4 Substrate | Non-substrate | 0.7989 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6504 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9732 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9516 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9504 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9147 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9616 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9496 |
| Non-inhibitor | 0.9297 | |
| AMES Toxicity | Non AMES toxic | 0.8500 |
| Carcinogens | Non-carcinogens | 0.9405 |
| Fish Toxicity | Low FHMT | 0.9736 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.7384 |
| Honey Bee Toxicity | Low HBT | 0.8172 |
| Biodegradation | Not ready biodegradable | 0.8632 |
| Acute Oral Toxicity | III | 0.8063 |
| Carcinogenicity (Three-class) | Non-required | 0.6254 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.2954 | LogS |
| Caco-2 Permeability | 1.3133 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7221 | LD50, mol/kg |
| Fish Toxicity | 2.8355 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.4476 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| (b) spinaches and similar leaves | 0252000 | European Union | 3 | 25/01/2016 | |
| Soyabeans (Moringa/drumstick tree seeds,) | 0401070 | European Union | 0.05* | 25/01/2016 | |
| Mustard seeds | 0401080 | European Union | 0.05* | 25/01/2016 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.05* | 25/01/2016 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 25/01/2016 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 25/01/2016 | |
| Others (2) | 0251990 | European Union | 3 | 25/01/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 25/01/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 25/01/2016 | |
| Others (2) | 0110990 | European Union | 0.05* | 25/01/2016 | |
| Tree nuts | 0120000 | European Union | 0.05* | 25/01/2016 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 25/01/2016 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 25/01/2016 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 25/01/2016 | |
| Chestnuts | 0120040 | European Union | 0.05* | 25/01/2016 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 25/01/2016 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 25/01/2016 | |
| Macadamias | 0120070 | European Union | 0.05* | 25/01/2016 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 25/01/2016 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.05* | 25/01/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Rapid determination of polar pesticides and plant growth regulators in fruits andvegetables by liquid chromatography/tandem mass spectrometry. | J Environ Sci Health B | 2018 May 22:1-10 | 29787687 |
| Simultaneous determination of neonicotinoid insecticides and insect growthregulators residues in honey using LC-MS/MS with anion exchanger-disposablepipette extraction. | J Chromatogr A | 2018 Jul 6 | 29735281 |
| Effects on metabolic parameters in young rats born with low birth weight afterexposure to a mixture of pesticides. | Sci Rep | 2018 Jan 10 | 29321614 |
| Plasma pharmacokinetics and tissue depletion of cyromazine and its metabolitemelamine following oral administration in laying chickens. | J Vet Pharmacol Ther | 2017 Oct | 27900792 |
| Interaction Between Metarhizium anisopliae (Met.) and the Insecticides Used forControlling House Fly (Diptera: Muscidae) in Poultry Farm of Malaysia. | J Med Entomol | 2017 Nov 7 | 28981905 |
| Analysis of melamine and analogs in complex matrices: Advances and trends. | J Sep Sci | 2017 Jan | 27723251 |
| Determination of polar pesticides in olive oil and olives by hydrophilicinteraction liquid chromatography coupled to tandem mass spectrometry and highresolution mass spectrometry. | Talanta | 2016 Sep 1 | 27343599 |
| Multi-residue analysis of pesticides, plant hormones, veterinary drugs and mycotoxins using HILIC chromatography - MS/MS in various food matrices. | Anal Chim Acta | 2016 Oct 26 | 27720116 |
| Determination of emerging nitrogenous economic adulterants in milk proteins byhigh-performance liquid chromatography/compact mass spectrometry. | Rapid Commun Mass Spectrom | 2016 Jun 15 | 27173108 |
| Trace residue analysis of dicyandiamide, cyromazine, and melamine in animaltissue foods by ultra-performance liquid chromatography. | J Food Drug Anal | 2016 Jul | 28911564 |
| Attapulgite Nanoparticles-Modified Monolithic Column for Hydrophilic In-TubeSolid-Phase Microextraction of Cyromazine and Melamine. | Anal Chem | 2016 Feb 2 | 26743944 |
| A novel dispersive micro solid phase extraction using PCX as the sorbent for the determination of melamine and cyromazine in milk and milk powder byUHPLC-HRMS/MS. | Talanta | 2015 Mar | 25618651 |
| Cyromazine imprinted polymers for selective stir bar sorptive extraction ofmelamine in animal feed and milk samples. | Analyst | 2015 Jun 21 | 25875596 |
| Highly sensitive determination of cyromazine, melamine, and their metabolites in milk by molecularly imprinted solid-phase extraction combined withultra-performance liquid chromatography. | J Dairy Sci | 2015 Apr | 25682136 |
| Choice of optimal biocide combination to control flies (Diptera: Muscidae). | Ann Agric Environ Med | 2015 | 26094516 |
| Rapid detection of pesticides not amenable to multi-residue methods by flowinjection-tandem mass spectrometry. | Anal Bioanal Chem | 2014 Nov | 24518902 |
| Determination of multi-class pesticide residue in dietary supplements from grape seed extracts by ultra-high-performance liquid chromatography coupled to triplequadrupole mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24945907 |
| A novel colloidal gold-based lateral flow immunoassay for rapid simultaneousdetection of cyromazine and melamine in foods of animal origin. | Food Chem | 2013 Jun 1 | 23411288 |
| [Rapid screening of 176 pesticide residues in vegetables by ultra fast liquidchromatography-tandem mass spectrometry]. | Se Pu | 2013 Jan | 23667993 |
| Simultaneous determination of cyromazine and dicyclanil in animal edible tissues using UPLC-MS/MS. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2013 | 23469982 |
Targets
- General Function:
- Interleukin-8 receptor binding
- Specific Function:
- IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response to an inflammatory stimulus. IL-8(6-77) has a 5-10-fold higher activity on neutrophil activation, IL-8(5-77) has increased activity on neutrophil activation and IL-8(7-77) has a higher affinity to receptors CXCR1 and CXCR2 as compared to IL-8(1-77), respectively.
- Gene Name:
- CXCL8
- Uniprot ID:
- P10145
- Molecular Weight:
- 11097.98 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]