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1. Gesamprim
1. 1912-24-9
2. Gesaprim
3. Oleogesaprim
4. Chromozin
5. Aktikon
6. Atranex
7. Atrazin
8. Argezin
9. Atazinax
10. Atrasine
11. Fenamin
12. Fenatrol
13. Gesoprim
14. Hungazin
15. Pitezin
16. Primatol
17. Primaze
18. Radazin
19. Strazine
20. Zeazine
21. Aatrex
22. Candex
23. Cyazin
24. Inakor
25. Vectal
26. Wonuk
27. Zeazin
28. Cekuzina-t
29. Actinite Pk
30. Aktinit A
31. Atratol A
32. Aktikon Pk
33. Aktinit Pk
34. Weedex A
35. Crisatrina
36. Crisazine
37. Fenamine
38. Aatram
39. Akticon
40. Atrataf
41. Atratol
42. Griffex
43. Radizin
44. Zeapos
45. Atred
46. Atrex
47. Primatol A
48. Hungazin Pk
49. Aatrex Nine-o
50. Vectal Sc
51. Herbatoxol
52. Zeopos
53. Triazine A 1294
54. Aatrex 4l
55. Farmco Atrazine
56. Gesaprim 50
57. Aatrex 80w
58. Aneldazin
59. Gesaprin
60. Radizine
61. Azoprim
62. Maizina
63. 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine
64. Geigy 30,027
65. Shell Atrazine Herbicide
66. 2-chloro-4-ethylamino-6-isopropylamino-s-triazine
67. Hungazin (van)
68. 1,3,5-triazine-2,4-diamine, 6-chloro-n-ethyl-n'-(1-methylethyl)-
69. Aatram 20g
70. Ceasin 50
71. Crisamina
72. Farmozine
73. Laddock
74. Mebazine
75. Fogard
76. 6-chloro-n-ethyl-n'-(1-methylethyl)-1,3,5-triazine-2,4-diamine
77. 2-chloro-4-ethylamineisopropylamine-s-triazine
78. 2-ethylamino-4-isopropylamino-6-chloro-s-triazine
79. A 361
80. Aatrex 4lc
81. Atrazine [ansi:bsi:iso]
82. Atraflow
83. Primoleo
84. Zeaphos
85. Attrex
86. Atraflow Plus
87. S-triazine, 2-chloro-4-(ethylamino)-6-(isopropylamino)-
88. G 30027
89. 1-chloro-3-ethylamino-5-isopropylamino-s-triazine
90. Radazin T
91. Atrazine 4l
92. Griffex 4l
93. Atrazine 80w
94. Azinotox 500
95. 2-chloro-4-(2-propylamino)-6-ethylamino-s-triazine
96. Ai3-28244
97. S-triazine, 2-chloro-4-ethylamino-6-isopropylamino-
98. 2-aethylamino-4-chlor-6-isopropylamino-1,3,5-triazin
99. 1-chloro-3-ethylamino-5-isopropylamino-2,4,6-triazine
100. 102029-43-6
101. 6-chloro-n-ethyl-n'-isopropyl-1,3,5-triazine-2,4-diamine
102. 2-chloro-4-(ethylamino)-6-(isopropylamino)-1,3,5-triazine
103. 6-chloro-n2-ethyl-n4-isopropyl-1,3,5-triazine-2,4-diamine
104. Qja9m5h4im
105. 2-chloro-4-isopropylamino-6-ethylamino -1,3,5-triazine
106. 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine
107. Dtxsid9020112
108. Chebi:15930
109. 2-aethylamino-4-chlor-6-isopropylamino-1,3,5-triazin [german]
110. 2-aethylamino-4-isopropylamino-6-chlor-1,3,5-triazin [german]
111. 6-chloro-n-ethyl-n'-(propan-2-yl)-1,3,5-triazine-2,4-diamine
112. 6-chloro-4-n-ethyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine
113. Atrazine 100 Microg/ml In Toluene
114. 1,3,5-triazine-2,4-diamine, 6-chloro-n-ethyl-n'-(1-methylethyl)- (9ci)
115. Atrazine 1000 Microg/ml In Acetone
116. Atrazine 10 Microg/ml In Cyclohexane
117. 2-aethylamino-4-isopropylamino-6-chlor-1,3,5-triazin
118. Atrazine 10 Microg/ml In Acetonitrile
119. Nsc-163046
120. 1-chloro-3-(ethylamino)-5-(isopropylamino)-s-triazine
121. 2-chloro-4-(2-propylamino)-6-(ethylamino)-s-triazine
122. 6-chloro-4-(ethylamino)-2-(isopropylamino)-s-triazine
123. Atrazine 100 Microg/ml In Acetonitrile
124. 2-chloro-4-isopropylamino-6-ethylamino-1,3,5-triazine
125. Dsstox_cid_112
126. 1,3,5-triazine-2,4-diamine, 6-chloro-n2-ethyl-n4-(1-methylethyl)-
127. 6-chloro-2-n-ethyl-4-n-(propan-2-yl)-1,3,5-triazine-2,4-diamine
128. Dsstox_rid_75374
129. Dsstox_gsid_20112
130. Atrazine, Analytical Standard
131. Caswell No. 063
132. 1-chloro-3-(ethylamino)-5-(isopropylamino)-2,4,6-triazine
133. Atrazine [iso]
134. Smr000255992
135. Cas-1912-24-9
136. Ccris 1025
137. Hsdb 413
138. Einecs 217-617-8
139. Unii-qja9m5h4im
140. Epa Pesticide Chemical Code 080803
141. Nsc 163046
142. Brn 0612020
143. Zeapho
144. Fermco Atrazine
145. 6-chloro-n2-ethyl-n4-(propan-2-yl)-1,3,5-triazine-2,4-diamine
146. Primitol A
147. Atrazine Solution
148. Oleogesaprim 200
149. Gesaprim 500
150. Mfcd00041810
151. Atrazine (unlabeled)
152. 2-chloro-4-ethylamino-6-isopropylamino-sym-triazine
153. Spectrum_001821
154. Atrazine [hsdb]
155. Atrazine [iarc]
156. Specplus_000422
157. 6-chloro-n4-ethyl-n2-isopropyl-1,3,5-triazine-2,4-diamine
158. Atrazine [mi]
159. Spectrum2_001880
160. Spectrum3_000821
161. Spectrum4_000661
162. Spectrum5_001954
163. Bmse000835
164. Ec 217-617-8
165. Oprea1_839865
166. Schembl36936
167. Bspbio_002341
168. Kbiogr_001061
169. Kbioss_002326
170. Spectrum330029
171. 2-chloro-4-ethylamino-6-isopropylamine-s-triazine
172. Mls000389718
173. Mls001055469
174. Bidd:er0403
175. Chembl15063
176. Divk1c_006518
177. 2-chloro-4-(ethylamino)-6-(isopropylamino)triazine
178. Spbio_001760
179. Schembl21045984
180. Kbio1_001462
181. Kbio2_002323
182. Kbio2_004891
183. Kbio2_007459
184. Kbio3_001841
185. Atrazine 1000 Ug/ml In Acetone
186. Hms2541c15
187. Hms3604n05
188. Bcp12774
189. Hy-n7091
190. Zinc3078958
191. Tox21_201986
192. Tox21_301021
193. Atrazine 100 Microg/ml In Methanol
194. Atrazine 200 Microg/ml In Methanol
195. Ccg-39357
196. Nsc163046
197. S5171
198. Stl115099
199. 6-chloro-n~2~-ethyl-n~4~-(propan-2-yl)-1,3,5-triazine-2,4-diamine
200. Akos001023901
201. Am84660
202. Db07392
203. Ncgc00090784-01
204. Ncgc00090784-02
205. Ncgc00090784-03
206. Ncgc00090784-04
207. Ncgc00090784-05
208. Ncgc00090784-06
209. Ncgc00090784-07
210. Ncgc00090784-08
211. Ncgc00090784-09
212. Ncgc00090784-10
213. Ncgc00254923-01
214. Ncgc00259535-01
215. Ac-12056
216. As-13785
217. Atrazine 1000 Microg/ml In Acetonitrile
218. Wln: T6n Cn Enj Bmy1&1 Dm2 Fg
219. Atrazine 2000 Microg/ml In Dichloromethane
220. Db-044759
221. Atrazine, Pestanal(r), Analytical Standard
222. Cs-0077590
223. Ft-0602866
224. Ft-0662335
225. C06551
226. F21351
227. 029a436
228. A813475
229. Ag-668/02857017
230. G-30027
231. Q408652
232. 2-aethylamino-4-chlor-6-isopropylamino-1,5-triazin
233. 2-chloro-4-ethyl-amino-6-isopropylamino-s-triazine
234. J-012357
235. Atrazine, Certified Reference Material, Tracecert(r)
236. Brd-k45535217-001-02-2
237. 1-chloro-3-(ethylamino)-5-(isopropylamino)-2,6-triazine
238. 2-chloro-4-(ethylamino)-6-(isopropylamino)-1,5-triazine
239. 1,5-triazine-2,4-diamine, 6-chloro-n-ethyl-n'-(1-methylethyl)-
240. 6-chloranyl-n4-ethyl-n2-propan-2-yl-1,3,5-triazine-2,4-diamine
241. 6-chloro-n-ethyl-n'-(1-methylethyl)-1,5-triazine-2,4-diamine
242. 6-chloro-n4-ethyl-n2-propan-2-yl-1,3,5-triazine-2,4-diamine
243. N-[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]-n-isopropylamine
244. 6-chloro-4-n-ethyl-2-n-(propan-2-yl)-1,2,3,4-tetrahydro-1,3,5-triazine-2,4-diimine
245. 6-chloro-n(sup 2)-ethyl-n(sup 4)-isopropyl-1,3,5-triazine-2,4-diamine
246. Atrazine Solution, 100 Mug/ml In Methanol, Pestanal(r), Analytical Standard
247. Atrazine Solution, Certified Reference Material, 1000 Mug/ml In Methyl Tert-butyl Ether
| Molecular Weight | 215.68 g/mol |
|---|---|
| Molecular Formula | C8H14ClN5 |
| XLogP3 | 2.6 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Exact Mass | 215.0937732 g/mol |
| Monoisotopic Mass | 215.0937732 g/mol |
| Topological Polar Surface Area | 62.7 Ų |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Complexity | 166 |
| 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 |
Herbicides
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)
Atrazine (ATR) is a widely used chlorotriazine herbicide, a ubiquitous environmental contaminant, and a potential developmental toxicant. To quantitatively evaluate placental/lactational transfer and fetal/neonatal tissue dosimetry of ATR and its major metabolites, physiologically based pharmacokinetic models were developed for rat dams, fetuses and neonates. These models were calibrated using pharmacokinetic data from rat dams repeatedly exposed (oral gavage; 5mg/kg) to ATR followed by model evaluation against other available rat data. Model simulations corresponded well to the majority of available experimental data and suggest that: (1) the fetus is exposed to both ATR and its major metabolite didealkylatrazine (DACT) at levels similar to maternal plasma levels, (2) the neonate is exposed mostly to DACT at levels two-thirds lower than maternal plasma or fetal levels, while lactational exposure to ATR is minimal, and (3) gestational carryover of DACT greatly affects its neonatal dosimetry up until mid-lactation. To test the model's cross-species extrapolation capability, a pharmacokinetic study was conducted with pregnant C57BL/6 mice exposed (oral gavage; 5mg/kg) to ATR from gestational day 12 to 18. By using mouse-specific parameters, the model predictions fitted well with the measured data, including placental ATR/DACT levels. However, fetal concentrations of DACT were overestimated by the model (10-fold). This overestimation suggests that only around 10% of the DACT that reaches the fetus is tissue-bound. These rodent models could be used in fetal/neonatal tissue dosimetry predictions to help design/interpret early life toxicity/pharmacokinetic studies with ATR and as a foundation for scaling to humans.
PMID:23958493 Lin Z et al; Toxicol Appl Pharmacol 273 (1): 140-58 (2013)
... The atrazine (ATZ) concentrations in urine samples of the workers collected from an atrazine plant were determined by /a gas chromatograph-electron capture detector/ method /for detecting ATZ and its metabolites (deethylatrazine (DEA), deisopropylatrazine (DIA), deethyldeisopropylatrazine (DEDIA)) in human urine/. The concentration ranges were 0.003 -0.301 mg/L for DEDIA, 0.005 -0.011 mg/L for DEA, 0.006 -0.276 mg/L for DIA, and 0.005 -0.012 mg/L for ATZ.
PMID:18161334 Xu R et al; Se Pu. 25 (5): 758-61 (2007)
Small amount of parent ... atrazine ... /was/ excreted in urine of cows fed unlabeled herbicide for 4 days.
Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 170
Seventy-two hr /after ingestion/ 65.5% of radiolabeled atrazine was found in urine of rats, while 20.3% was found in the feces. Less than 0.1% was found in expired air, thus indicating s-triazine ring was not appreciably metabolized to carbon dioxide. Tissue analysis revealed that 15.8% of reactivity was retained, with high concentrations observed in the liver, kidney, and lung, and lower concentrations observed in muscle tissue and fat.
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2
For more Absorption, Distribution and Excretion (Complete) data for Atrazine (7 total), please visit the HSDB record page.
Atrazine (ATR) is a widely used chlorotriazine herbicide, a ubiquitous environmental contaminant, and a potential developmental toxicant. To quantitatively evaluate placental/lactational transfer and fetal/neonatal tissue dosimetry of ATR and its major metabolites, physiologically based pharmacokinetic models were developed for rat dams, fetuses and neonates. These models were calibrated using pharmacokinetic data from rat dams repeatedly exposed (oral gavage; 5mg/kg) to ATR followed by model evaluation against other available rat data. Model simulations corresponded well to the majority of available experimental data and suggest that: (1) the fetus is exposed to both ATR and its major metabolite didealkylatrazine (DACT) at levels similar to maternal plasma levels, (2) the neonate is exposed mostly to DACT at levels two-thirds lower than maternal plasma or fetal levels, while lactational exposure to ATR is minimal, and (3) gestational carryover of DACT greatly affects its neonatal dosimetry up until mid-lactation. To test the model's cross-species extrapolation capability, a pharmacokinetic study was conducted with pregnant C57BL/6 mice exposed (oral gavage; 5mg/kg) to ATR from gestational day 12 to 18. By using mouse-specific parameters, the model predictions fitted well with the measured data, including placental ATR/DACT levels. However, fetal concentrations of DACT were overestimated by the model (10-fold). This overestimation suggests that only around 10% of the DACT that reaches the fetus is tissue-bound. These rodent models could be used in fetal/neonatal tissue dosimetry predictions to help design/interpret early life toxicity/pharmacokinetic studies with ATR and as a foundation for scaling to humans.
PMID:23958493 Lin Z et al; Toxicol Appl Pharmacol 273 (1): 140-58 (2013)
Atrazine (ATR) is a widely used herbicide. There are several types of reactions in its metabolism. Herein, the mechanism of three paths of hydrolysis reactions in its metabolism and predictions of toxicities of its metabolites in the three paths will be presented. The calculation results by B3LYP (Becke, 3-parameter, Lee-Yang-Parr), one of the approaches in density functional theory, indicated that (1) there were three models in the three hydrolysis paths of ATR. The dissociation mechanisms of C(9/11)-N(8/10), C(4/6)-N(8/10), and C-Cl were dealkylation, deamination, and Cl substitution, respectively. (2) The energy barrier of C-Cl dissociation was lower. The dissociation was advantageous in dynamics and the primary reaction in the three hydrolysis paths. In these hydrolysis reactions, the different intermediates had different concentrations because of the impact of the reaction rate. (3) In addition, it was necessary to consider the solvent effect to investigate hydrolysis reaction. The conductor-like polarizable continuum model (CPCM) was used to simulate the hydrolysis reaction in bond length and energy barrier because of the solvent effect. Experimental or predictive results showed that atrazine and its metabolites in the three hydrolysis paths were carcinogenic.
PMID:24807108 Li J et al; J Agric Food Chem 62 (21): 4852-63 (2014)
Compounds of the s-triazine family are among the most heavily used herbicides over the last 30 years. Some of these derivatives are suspected to be carcinogens. In this study the identity of specific phase-I enzymes involved in the metabolism of s-triazine derivatives (atrazine, terbuthylazine, ametryne, and terbutryne) by human liver microsomes was determined. Kinetic studies demonstrated biphasic kinetics for all pathways examined (S-oxidation, N-dealkylation, and side-chain C-oxidation). Low Km values were in a range of about 1-20 uM, whereas high Km values were up to 2 orders of magnitude higher. For a correlation study, 30 human liver microsomal preparations were screened for seven specific P450 activities, and these were compared to activities for the metabolites derived from these s-triazines. A highly significant correlation in the high-affinity concentration range was seen with cytochrome P450 1A2 activities. Chemical inhibition was most effective with alpha-naphthoflavone an furafylline at low s-triazine concentrations and additionally with ketoconazole and gestodene at high substrate concentrations. Studies with 10 heterologously expressed P450 forms demonstrated that several P450 enzymes are capable of oxidizing these s-triazines, with different affinities and regioselectivities. P450 1A2 was confirmed to be the low-Km P450 enzyme involved in the metabolism of these s-triazines. A potential participation of flavin-containing monooxygenases (FMOs) in sulfoxidation reactions of the thiomethyl derivatives ametryne and terbutryne in human liver was also evaluated. Sulfoxide formation in human inhibition indicated no significant involvement of flavin-containing monooxygenases. Finally, purified recombinant FMO3, the major flavin-containing monooxygenase in human liver, exhibited no significant activity (< 0.1 nmol (nmol of FMO3)-1 min-1) in the formation of the parent sulfoxides of ametryne and terbutryne. Therefore, P450 1A2 alone is likely to be responsible for the hepatic oxidative phase-I metabolism of the s-triazine derivatives in exposed humans.
PMID:9305587 Lang DH et al; Chemical Research in Toxicology 10 (9): 1037-1044 (1997)
A large number of urinary metabolites was isolated and 15.8% was detected in the carcasses at 72 hr post-exposure. Dealkylation of atrazine in vitro, predominated over glutathione conjugation. Metabolites identified from rat and rabbit urine contained an intact triazine ring suggesting initial loss of ethyl or methyl groups from the alkyl side chains. In the miniature pig, atrazine and its metabolites were seen in urine for slightly more than 24 hr; diethylatrazine was also identified. Excretion by sheep and cattle is rapid with no residues seen in the milk of cows receiving 5 ppm atrazine in the diet for 4 days.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 1246
For more Metabolism/Metabolites (Complete) data for Atrazine (16 total), please visit the HSDB record page.
The whole body half-life of elimination /in rats/ was determined as 31.3 +/- 2.8 hours...
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Atrazine (1912-24-9) p.31 (January 28, 2008). Available from, as of October 17, 2017: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm
Atrazine (ATZ) is probably the most widely used herbicide in the world. However there are still many controversies regarding its impacts on human health. Our investigations on the role of pesticides in liver dysfunctions have led us to detect an inhibition of FSP1 expression of 70% at 50 um and around 95% at 500 uM of ATZ (p<0.01). This gene encodes the protein S100a4 and is a clinical biomarker of epithelial-mesenchymal transition (EMT), a key step in the metastatic process. Here we investigated the possible effect of ATZ on cell migration and noticed that it prevents the EMT and motility of the HepG2 cells induced by the phorbol ester TPA. ATZ decreases Fak pathway activation but has no effect on the Erk1/2 pathway known to be involved in metastasis in this cell line. These results suggest that ATZ could be involved in cell homeostasis perturbation, potentially through a S100a4-dependant mechanism.
PMID:24211529 Peyre L et al; Toxicol In Vitro 28 (2): 156-63 (2014)
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