1. 2-cyclopropylamino-4,6-diamino-s-triazine
2. Cga 72662
3. Cga-72662
4. Cyromazin
5. Cyromazine Dihydrochloride
6. Larvadex
7. N-cyclopropyl-1,3,5-triazine-2,4,6-triamine
8. N-cyclopropylmelamine
9. Neporex
10. Vetrazin
1. 66215-27-8
2. Larvadex
3. Vetrazin
4. Neporex
5. Cyromazin
6. Trigard
7. Cyclopropylmelamine
8. Cypromazine
9. Vetrazine
10. Citation
11. N-cyclopropyl-1,3,5-triazine-2,4,6-triamine
12. Azimethiphos
13. Cga 72662
14. 2-cyclopropylamino-4,6-diamino-s-triazine
15. Armor
16. N-cyclopropylmelamine
17. Vetrazin (pesticide)
18. 1,3,5-triazine-2,4,6-triamine, N-cyclopropyl-
19. Cyromazinum
20. Ciromazina
21. Larvadex Premix
22. N-cyclopropyl-2,4,6-triamino-1,3,5-triazine
23. N2-cyclopropyl-1,3,5-triazine-2,4,6-triamine
24. Oms-2014
25. 2-n-cyclopropyl-1,3,5-triazine-2,4,6-triamine
26. 2,4-diamino-6-(cyclopropylamino)-s-triazine
27. Cga-72662
28. Neporex (tn)
29. Cyromazine [ansi:bsi:iso]
30. Ai3-52713
31. Cyromazin;cga-72662
32. Nsc-759268
33. Ca49y29ra9
34. Chebi:30260
35. Cyromazine (inn)
36. N~2~-cyclopropyl-1,3,5-triazine-2,4,6-triamine
37. N-cyclopropyltriazine-2,4,6-triamine
38. Diamino-6-(cyclopropylamino)-s-triazine
39. Ncgc00163803-03
40. Cyromazine [inn]
41. Dsstox_cid_3999
42. Cyclopropyl-1,3,5-triazine-2,4,6-triamine
43. Dsstox_rid_77253
44. Dsstox_gsid_23999
45. N(2)-cyclopropyl-1,3,5-triazine-2,4,6-triamine
46. Caswell No. 167b
47. Cyromazine [ban:inn]
48. Cyromazinum [inn-latin]
49. Ciromazina [inn-spanish]
50. Cas-66215-27-8
51. N2-cyclopropylmelamine
52. Hsdb 6602
53. Cyromazine D4 (cyclopropyl-2,2,3,3 D4)
54. 4-n-cyclopropyl-1,3,5-triazine-2,4,6-triamine
55. Einecs 266-257-8
56. Brn 0882879
57. Unii-ca49y29ra9
58. Cyromazine [usp:inn:ban]
59. Neoprex
60. N-cyclopropyl-1,3,5-triazin-2,4,6-triamine
61. Ax3
62. Mfcd00078650
63. Cyromazine [mi]
64. Cyromazine (usp/inn)
65. Cyromazine [iso]
66. Cyromazine [hsdb]
67. Cyromazine [mart.]
68. 2,4-diamino-6-cyclopropylamino-1,3,5-triazine
69. Cyromazine [usp-rs]
70. Schembl27231
71. 2,4-diamino-6-(cyclopropylamino)-1,3,5-triazine
72. 2,4-diamino-6-(cyclopropylamino)-s-triazine (8ci)
73. Zinc1239
74. Chembl1231107
75. Dtxsid6023999
76. Cyromazine (n-clopropyl-1,3,5-triazine-2,4,6-triamine)
77. Cyromazine [usp Impurity]
78. Hms3264k09
79. Hms3652n03
80. Pharmakon1600-01505903
81. Bcp13527
82. Hy-b1331
83. Tox21_112074
84. Tox21_201846
85. Tox21_300784
86. Nsc759268
87. S4167
88. Akos007930524
89. Cyromazine 100 Microg/ml In Methanol
90. Tox21_112074_1
91. Ac-6858
92. Ccg-213992
93. Cs-4864
94. Nsc 759268
95. Cyromazine 1000 Microg/ml In Methanol
96. Cyromazine-(cyclopropyl-2,2,3,3-d4)
97. Ncgc00163803-01
98. Ncgc00163803-02
99. Ncgc00163803-04
100. Ncgc00163803-05
101. Ncgc00163803-06
102. Ncgc00254688-01
103. Ncgc00259395-01
104. 2cyclopropylamino-4,6-diamino-s-triazine
105. As-12700
106. Cyromazine 100 Microg/ml In Acetonitrile
107. 2,4-diamino-6-cyclopropylamino-s-triazine
108. Db-054884
109. Ft-0603144
110. Ft-0665421
111. Sw220183-1
112. Cyromazin, Pestanal(r), Analytical Standard
113. A16473
114. D07767
115. D89506
116. Ab01563373_01
117. Ab01563373_02
118. 215c278
119. A835367
120. Q412423
121. Sr-01000944274
122. Q-200914
123. Sr-01000944274-1
124. N-cyclopropyl-1,3,5-triazine-2,4,6-triamine, 9ci
125. N-cyclopropyl-2,4,6-triamino-1,3,5-triazine, 97%
126. Cyromazin (n-cyclopropyl- 1,3,5-triazine-2,4,6-triamine)
127. Cyromazine, United States Pharmacopeia (usp) Reference Standard
128. N2-cyclopropyl-1,3,5-triazine-2,4,6-triamine;n-cyclopropyl-2,4,6-triamino-1,3,5-triazine
| Molecular Weight | 166.18 g/mol |
|---|---|
| Molecular Formula | C6H10N6 |
| XLogP3 | -0.2 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 2 |
| Exact Mass | 166.09669434 g/mol |
| Monoisotopic Mass | 166.09669434 g/mol |
| Topological Polar Surface Area | 103 Ų |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Complexity | 148 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
MEDICATION (VET): ectoparasiticide
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 466
MEDICATION (VET): Cyromazine, a triazine derivative, is effective against blowfly larvae on sheep and lambs and also against other Diptera such as houseflies and mosquitos. At recommended dose rates, cyromazine shows only limited activity against established strikes and must therefore be used preventively. Blowflies usually lay eggs on damp fleece of treated sheep. Although larvae are able to hatch, the young larvae immediately come into contact with cyromazine, which prevents the molt to second instars. The efficacy of a pour-on preparation of cyromazine does not depend on factors such as weather, fleece length, and whether the fleece is wet or dry. Control can be maintained for up to 13 wk after a single pour-on application, or longer if cyromazine is applied by dip or shower.
Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2163
Insecticides
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)
Dermal Absorption /in rats/ ... at 10 hrs = 13 %. Cyromazine /was/ apparently rapidly absorbed into the skin in an inverse dose related manner. The absorption into the skin is followed by a slower release into the body. The main route of excretion is apparently by the urine. There is no evidence that the compound is sequestered in the skin. Mean absorption based on blood, urinary/ fecal excretion, and carcass, ranged from 0.6 to 7% for animals sacrificed at the end of the exposure periods. For animals exposed for 10 and 24 hours and followed for 48 hours post-exposure, mean absorption ranged from 8 to 14.5%. Total radioactivity absorbed generally decreased as dose increased indicating saturation of absorption with increasing dose. Amounts remaining in/on the skin at termination ranged from 4.5% (10 mg dose/2 hr exposure) to 24% ( 0.1 mg dose/24 hr exposure). The majority of the absorbed radioactivity was found in the urine and carcass. Most of the unabsorbed radioactivity was found in the skin washes from each dose/ duration. /In another portion of the same study in rats/ absorption at 10 hrs = 10%. Mean total recoveries of applied radioactivity from all dose groups ranged from 85 to 101%. Mean absorption based on blood, urinary/ fecal excretion, and carcass, ranged from 2% to 11%. Total radioactivity absorbed generally increased with increasing exposure time but decreased with increasing dose indicating saturation of penetration with increasing dose. The majority of the absorbed radioactivity was found in the urine and carcass. Most of the unabsorbed radioactivity was found in the skin washes from each dose/duration (35-90%). However, based on measurements of skin absorption, a significant amount of radioactive dose was also found in the skin itself (9-40%). Mean absorption with inclusion of radioactivity in dissolved skin ranged from 10 to 45%. The ratio of the amount of radioactive dose in the skin wash to the radioactivity in the skin itself decreased with time indicating penetration into the subsurface of the skin with time after treatment.
USEPA; Rules and Regulations. Cyromazine; Pesticide Tolerance. 68 FR 55261 (September 24, 2003)
Cyromazine was well absorbed after oral administration /to rats/. Excretion was rapid at the dose (3 mg/kg), but an apparent delay in excretion occurred at the high dose (300 mg/kg). Fecal elimination was equivalent among dose groups except the high dose males, where a greater percentage was eliminated by this route. The origin of fecal radioactivity was via biliary elimination. Residual radioactivity in tissues was minimal in all dose groups. Urinary and fecal metabolites of 14C-cyromazine were isolated and identified by TLC, HPLC, and GC/MS. The major compounds were the N-dealkylated product melamine, hydroxycyromazine, and unmetabolized cyromazine identified
USEPA; Rules and Regulations. Cyromazine; Pesticide Tolerance. 68 FR 55261 (September 24, 2003)
A single dose of 0.5 mg/kg bw of 14C-cyromazine (uniformly triazine ring labeled) was given orally to two male and one female Charles River white rats (not further identified). By 72 hours after dosing, 95% of the administered dose had been excreted in urine, essentially all within the first 24 hours. About 3% was excreted in feces, again predominantly in the first 24 hours. Negligible amounts were excreted as volatiles or CO2 in another two males and one female given the same dose. Tissue residues were below the level of detection except in liver; however, liver levels were too low to permit accurate quantitation (about 0.007 ppm).
Joint FAO/WHO Meeting on Pesticide Residues in Food. Evaluations (1990) Toxicology. Cyromazine (September 1990). Available from, as of June 8, 2007: https://www.inchem.org/documents/jmpr/jmpmono/v90pr01.htm
Two chickens (strain not indicated) were given daily oral doses of 14C-cyromazine (uniformly triazine ring labeled) of 0.75 mg/hen/day by capsule for seven days. By 24 hours after the last dose 99.1% of the administered radioactivity had been recovered in the excreta with essentially none in volatiles and CO2. Both egg whites and egg yolks contained about 0.12-0.15 ppm consistently. Tissue levels were: byproducts (i.e. head and feet) 0.047 ppm test material equivalents; reproductive tract 0.047 ppm; liver 0.032 ppm; all other tissues 0.008-0.019 ppm.
Joint FAO/WHO Meeting on Pesticide Residues in Food. Evaluations (1990) Toxicology. Cyromazine (September 1990). Available from, as of June 8, 2007: https://www.inchem.org/documents/jmpr/jmpmono/v90pr01.htm
For more Absorption, Distribution and Excretion (Complete) data for CYROMAZINE (10 total), please visit the HSDB record page.
Cyromazine was well absorbed after oral administration /to rats/. ... Urinary and fecal metabolites of 14C-cyromazine were isolated and identified by TLC, HPLC, and GC/MS. The major compounds were the N-dealkylated product melamine, hydroxycyromazine, and unmetabolized cyromazine identified.
USEPA; Rules and Regulations. Cyromazine; Pesticide Tolerance. 68 FR 55261 (September 24, 2003)
Urine from a female rat given a single oral dose of 14C-cyromazine (uniformly triazine ring labeled) of 0.5 mg/kg bw was analyzed using TLC and a cation exchange column chromatography system. With both systems the majority of the urinary radioactivity was determined to be in the form of unchanged parent compound. Unchanged parent compound in urine accounted for about 80% of the administered dose. Three metabolites were detected with each system and were presumed to be the same compounds. These metabolites accounted for 2.2-3.2%, 3.0-5.5%, and 4.6-5.3% of the administered dose, respectively, but no identification was made. Fecal material from a male rat given the same dose as the above female was found to contain little unchanged parent compound: <0.1% of the administered dose. The same three metabolites as observed in urine were found and represented 0.1, 0.1 and 4.1% of the administered dose, respectively.
Joint FAO/WHO Meeting on Pesticide Residues in Food. Evaluations (1990) Toxicology. Cyromazine (September 1990). Available from, as of June 8, 2007: https://www.inchem.org/documents/jmpr/jmpmono/v90pr01.htm
One male and one female albino Sprague-Dawley rats were given diet containing 3000 ppm of 14C-cyromazine for 10 days. In the male the liver was found to contain 31.3 ppm cyromazine and 0.96 ppm melamine and the kidney 62.4 ppm cyromazine and 1.3 ppm melamine. In the female liver residues were 13.2 ppm and 0.51 ppm and kidney residues 22.2 and 0.68 ppm of cyromazine and melamine, respectively. This study indicated that there was some conversion of cyromazine to melamine in vivo.
Joint FAO/WHO Meeting on Pesticide Residues in Food. Evaluations (1990) Toxicology. Cyromazine (September 1990). Available from, as of June 8, 2007: https://www.inchem.org/documents/jmpr/jmpmono/v90pr01.htm
Urine from male and female monkeys (Macaca fasicicula) given single oral doses of 14C-cyromazine (uniformly triazine ring labeled) of 0.05 or 0.5 mg/kg bw by capsule was found to have the majority of the radioactivity present in the form of unchanged parent compound. Regardless of dose 93.6-96.1% of the urinary radioactivity was present as unchanged cyromazine. Additionally, 2.9-6.4% of the radioactivity as identified as melamine ... In a second study with the same strain of monkey given the same dose levels, urine collected during the first 24 hours after dosing had 95-100% of the recovered radioactivity in the form of unchanged cyromazine. In one male dosed at 0.05 mg/kg bw, no melamine was detected in the urine. In one female at 0.05 mg/kg bw and one monkey of each sex given 0.5 mg/kg bw 3.0-3.9% of the urinary radioactivity was in the form of melamine.
Joint FAO/WHO Meeting on Pesticide Residues in Food. Evaluations (1990) Toxicology. Cyromazine (September 1990). Available from, as of June 8, 2007: https://www.inchem.org/documents/jmpr/jmpmono/v90pr01.htm
For more Metabolism/Metabolites (Complete) data for CYROMAZINE (9 total), please visit the HSDB record page.
Insect growth regulator with contact action, which interferes with moulting and pupation. When used on plants, action is systemic.
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A607/Aug 87
Cyromazine is an effective insecticide used to control dipteran insects. Its precise mode of action is yet to be determined, although it has been suggested that it interferes with the hormone system, sclerotization of the cuticle, or nucleic acid metabolism. To understand the way in which cyromazine acts, /the authors/ positionally cloned a cyromazine resistance gene from Drosophila melanogaster. Six cyromazine resistance alleles had previously been generated by ethyl methanasulfonate treatment. Two of these failed to complement each other and here /the authors/ identify them as having independent non-sense mutations in CG32743, which is an ortholog of Smg1 of worms and mammals and encodes a phosphatidylinositol kinase-like kinase (PIKK). RNAi experiments confirm that cyromazine resistance can be achieved by knocking down CG32743. These are the first cyromazine resistant mutations identified at the nucleotide level. In mammals Smg1 phosphorylates P53 in response to DNA damage. This finding supports the hypothesis that cyromazine interferes with nucleic acid metabolism.
PMID:16640728 Chen Z et al; Insect Mol Biol 15 (2): 181-6 (2006)
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