SIMAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H12ClN5
Molecular Weight	201.657
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNC1=NC(NCC)=NC(Cl)=N1

InChI

InChIKey=ODCWYMIRDDJXKW-UHFFFAOYSA-N

InChI=1S/C7H12ClN5/c1-3-9-6-11-5(8)12-7(13-6)10-4-2/h3-4H2,1-2H3,(H2,9,10,11,12,13)

HIDE SMILES / InChI

Molecular Formula	C7H12ClN5
Molecular Weight	201.657
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/17193734
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28486186 | https://www.ncbi.nlm.nih.gov/pubmed/25078261 | https://www.ncbi.nlm.nih.gov/pubmed/26955487

Simazine is a selective triazine herbicide, that used to control broad-leaved weeds and annual grasses in a field, berry fruit, vegetable and ornamental crops, on turfgrass, and in orchards and vineyards. At higher rates, it is used for nonselective weed control in industrial areas. Before 1992, simazine was used to control submerged weeds and algae in large aquariums, farm ponds, fish hatcheries, swimming pools, ornamental ponds and cooling towers. Simazine is available in wettable powder, water dispersible granule, liquid and granular formulations. Simazine is highly toxic if inhaled, moderately toxic if ingested, and slightly toxic via dermal exposure. No cases of poisoning in humans have been reported from ingestion of Simazine.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
photosynthesis 1 Target ID: GO:0015979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17193734	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Failure of chloro-S-triazine-derived compounds to induce estrogen receptor-mediated responses in vivo and in vitro.	1996 Mar	8812239
The inhibition of estrogen receptor-mediated responses by chloro-S-triazine-derived compounds is dependent on estradiol concentration in yeast.	1996 Oct 3	8858116
Changes in rat liver cytochrome P450 enzymes by atrazine and simazine treatment.	1998 Jul	9711812
2-Chloro-s-triazine herbicides induce aromatase (CYP19) activity in H295R human adrenocortical carcinoma cells: a novel mechanism for estrogenicity?	2000 Mar	10746939
Effects of selected herbicides on cytokine production in vitro.	2000 May 19	10883730
Role of prolactin in chloro-S-triazine rat mammary tumorigenesis.	2000 Nov	11071396
Optimizing microwave-assisted solvent extraction (MASE) of pesticides from soil.	2001 Jan	11281258
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
Herbicide transport to surface waters at field and watershed scales in a Mediterranean vineyard area.	2001 May-Jun	11401289
Major herbicides in ground water: results from the National Water-Quality Assessment.	2001 May-Jun	11401272
Effects of chloro-s-triazine herbicides and metabolites on aromatase activity in various human cell lines and on vitellogenin production in male carp hepatocytes.	2001 Oct	11675267
Differentiating nonpoint sources of deisopropylatrazine in surface water using discrimination diagrams.	2001 Sep-Oct	11577893
Fate of pesticides in tropical soils of Brazil under field conditions.	2002 Jan-Feb	11837430
Selective sensing of triazine herbicides in imprinted membranes using ion-sensitive field-effect transistors and microgravimetric quartz crystal microbalance measurements.	2002 Nov	12475039
Influence of plant age and size on simazine toxicity and uptake.	2002 Nov-Dec	12469861
Field effects of simazine at lower trophic levels--a review.	2002 Sep 16	12398331
Movement of simazine in runoff water and weed control from citrus orchard as affected by reduced rate of herbicide application.	2003 Feb	12688468
Simazine runoff from citrus orchards affected by shallow mechanical incorporation.	2003 Jan-Feb	12549545
Prostate cancer risk in California farm workers.	2003 Mar	12661182
Simazine and metolachlor removal by subsurface flow constructed wetlands.	2003 Mar-Apr	12772955
Potential mechanisms responsible for chlorotriazine-induced alterations in catecholamines in pheochromocytoma (PC12) cells.	2003 Oct 31	14550852
Effect of endocrine disrupting chemicals on lipopolysaccharide-induced tumor necrosis factor-alpha and nitric oxide production by mouse macrophages.	2004 Jul	15256756
Induction of apoptosis by yomogin in human promyelocytic leukemic HL-60 cells.	2004 Jul	15256749
Measured concentrations of herbicides and model predictions of atrazine fate in the Patuxent River estuary.	2004 Mar-Apr	15074811
The combined antiandrogenic effects of five commonly used pesticides.	2004 Nov 15	15519604
Transgenic rice plants expressing human CYP1A1 remediate the triazine herbicides atrazine and simazine.	2005 Nov 2	16248553
Simazine biodegradation in soil: analysis of bacterial community structure by in situ hybridization.	2005 Sep	16015577
Sorption of pesticides on kaolinite and montmorillonite as a function of hydrophilicity.	2006	16753953
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Effects of possible endocrine disrupting chemicals on bacterial component-induced activation of NF-kappaB.	2006 Oct	17015962
Atrazine-induced aromatase expression is SF-1 dependent: implications for endocrine disruption in wildlife and reproductive cancers in humans.	2007 May	17520059
Effects of possible endocrine disruptors on MyD88-independent TLR4 signaling.	2008 Mar	18177342
Occurrence and fate of pesticides in four contrasting agricultural settings in the United States.	2008 May-Jun	18453432
Trial femoral head loss in to the soft tissues of pelvis during primary total hip replacement: a case report.	2008 Sep 12	18789144
Effect of a subchronic exposure to simazine on energetic metabolism of common carp (Cyprinus carpio).	2009 Feb	19130373
Chlorotriazine herbicides and metabolites activate an ACTH-dependent release of corticosterone in male Wistar rats.	2009 Nov	19690231
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010 Mar 15	20143881
In vivo alternative assessment of the chemicals that interfere with anterior pituitary POMC expression and interrenal steroidogenesis in POMC: EGFP transgenic zebrafish.	2010 Nov 1	20732339
Urinary biomarkers of prenatal atrazine exposure and adverse birth outcomes in the PELAGIE birth cohort.	2011 Jul	21367690
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.	2011 Mar 28	21251949
Disturbed relaxin signaling pathway and testicular dysfunction in mouse offspring upon maternal exposure to simazine.	2012	22984576

Patents

Sample Use Guides

In Vivo Use Guide

Rats and guinea pigs fed 100 mg/kg daily for 6 months had decreased weight gain, increased white blood cell counts, decreased blood cholinesterase activity and deterioration and inflammation of the stomach. In a 28-day study, oral doses of 2,500 mg/kg/day to rats resulted in stomach ulcers, damage to the small intestine, and death

Route of Administration: Oral

In Vitro Use Guide

MCF-7 and MDA-MB-231 cells were seeded into 96-well plates either in maintenance media (MCF-7 and MDA-MB-231) or in reduced media (MCF-7). Twenty-four hours after plating, the media were replaced with maintenance (MCF-7 and MDA-MB-231) or reduced (MCF-7) media containing atrazine, simazine, or cyanazine at 0.1-, 1-, and 10-fold the EPA safe levels or DMSO control. Atrazine was added at 0.3, 3.0, or 30 ppb (𝜇g/L; 0.64–64 𝜇M), cyanazine was added at 0.1, 1.0, or 10 ppb (0.17–17 𝜇M), and simazine was added at 0.4, 4.0, or 40 ppb (0.92–92 𝜇M). After twenty-four hours, 3 𝜇g resazurin was added and allowed to incubate for three hours prior to reading absorbance at 570 and 595nm on iMark Microplate Absorbance Reader (Bio-Rad, Hercules, CA).We performed univariate analysis of variance (ANOVA) using SPSS

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:02:39 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:39 GMT 2023`
Record UNII	SG0C34SMY3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SIMAZINE

Common Name

English

SIMAZINE [HSDB]

Common Name

English

6-CHLORO-N,N'-DIETHYL-1,3,5-TRIAZINE-2,4-DIAMINE

Systematic Name

English

SIMAZINE [ISO]

Common Name

English

6-CHLORO-N(SUP 2),N(SUP 4)-DIETHYL-1,3,5-TRIAZINE-2,4-DIAMINE

Systematic Name

English

NSC-25999

Code

English

SIMAZINE [MI]

Common Name

English

SIMAZINE [IARC]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

80807