Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H8Cl6O |
| Molecular Weight | 380.909 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=C(Cl)[C@]2(Cl)[C@@H]3[C@@H]4C[C@@H]([C@H]5O[C@@H]45)[C@@H]3[C@@]1(Cl)C2(Cl)Cl
InChI
InChIKey=DFBKLUNHFCTMDC-PICURKEMSA-N
InChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11-
| Molecular Formula | C12H8Cl6O |
| Molecular Weight | 380.909 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Dieldrin is an organochlorine pesticide belonging to the class of substances which are known to have a toxic effect on various physiological systems of the human body. Despite an imposed ban on their manufacture and commercial use, these pesticides can still be detected in high probability areas of consumption such as agriculture land. Dieldrin has been epidemiologically associated with an increased risk for Parkinson's disease (PD). Early studies identifying dieldrin as an antiandrogen estrogen mimetic have been contradicted by more recent studies which do not show any estrogenic activity.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study. | 2015-05 |
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| Environmental contaminants activate human and polar bear (Ursus maritimus) pregnane X receptors (PXR, NR1I2) differently. | 2015-04-01 |
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| A concentration addition model to assess activation of the pregnane X receptor (PXR) by pesticide mixtures found in the French diet. | 2014-09 |
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| Pesticide exposure and depression among male private pesticide applicators in the agricultural health study. | 2014-09 |
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| Pesticide use and incident diabetes among wives of farmers in the Agricultural Health Study. | 2014-09 |
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| The effect of in vitro dieldrin exposure on the rat paraoxonase 1 (pon1) promoter. | 2014-05 |
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| Regulation of hepatic drug transporter activity and expression by organochlorine pesticides. | 2014-03 |
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| The novel isoxazoline ectoparasiticide fluralaner: selective inhibition of arthropod γ-aminobutyric acid- and L-glutamate-gated chloride channels and insecticidal/acaricidal activity. | 2014-02 |
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| Sexually dimorphic transcriptomic responses in the teleostean hypothalamus: a case study with the organochlorine pesticide dieldrin. | 2013-01 |
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| Characteristic molecular signature for early detection and prediction of persistent organic pollutants in rat liver. | 2012-12-04 |
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| Comparison of chemical-induced changes in proliferation and apoptosis in human and mouse neuroprogenitor cells. | 2012-12 |
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| Does mechanism matter? Unrelated neurotoxicants converge on cell cycle and apoptosis during neurodifferentiation. | 2012-07 |
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| Environmental neurotoxic pesticide dieldrin activates a non receptor tyrosine kinase to promote PKCδ-mediated dopaminergic apoptosis in a dopaminergic neuronal cell model. | 2011-10 |
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| Differential effects of a complex organochlorine mixture on the proliferation of breast cancer cell lines. | 2011-04 |
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| Differential estrogenic effects of the persistent organochlorine pesticides dieldrin, endosulfan, and lindane in primary neuronal cultures. | 2011-04 |
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| Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. | 2011-02-27 |
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| Diverse neurotoxicants converge on gene expression for neuropeptides and their receptors in an in vitro model of neurodifferentiation: effects of chlorpyrifos, diazinon, dieldrin and divalent nickel in PC12 cells. | 2010-09-24 |
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| Genomic and proteomic responses to environmentally relevant exposures to dieldrin: indicators of neurodegeneration? | 2010-09 |
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| Transcriptional profiles for glutamate transporters reveal differences between organophosphates but similarities with unrelated neurotoxicants. | 2010-08-30 |
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| Effects of acute dieldrin exposure on neurotransmitters and global gene transcription in largemouth bass (Micropterus salmoides) hypothalamus. | 2010-08 |
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| Organochlorine pesticides dieldrin and lindane induce cooperative toxicity in dopaminergic neurons: role of oxidative stress. | 2010-03 |
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| Reduction of glutamatergic neurotransmission by prolonged exposure to dieldrin involves NMDA receptor internalization and metabotropic glutamate receptor 5 downregulation. | 2010-01 |
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| Differential effects exerted on human mammary epithelial cells by environmentally relevant organochlorine pesticides either individually or in combination. | 2009-08-14 |
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| Pesticide exposure and risk of monoclonal gammopathy of undetermined significance in the Agricultural Health Study. | 2009-06-18 |
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| Differential regulation of dopamine transporter function and location by low concentrations of environmental estrogens and 17beta-estradiol. | 2009-05 |
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| Oxidative and excitatory mechanisms of developmental neurotoxicity: transcriptional profiles for chlorpyrifos, diazinon, dieldrin, and divalent nickel in PC12 cells. | 2009-04 |
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| Transcriptional profiles reveal similarities and differences in the effects of developmental neurotoxicants on differentiation into neurotransmitter phenotypes in PC12 cells. | 2009-03-16 |
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| Developmental neurotoxicants target neurodifferentiation into the serotonin phenotype: Chlorpyrifos, diazinon, dieldrin and divalent nickel. | 2008-12-01 |
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| Unrelated developmental neurotoxicants elicit similar transcriptional profiles for effects on neurotrophic factors and their receptors in an in vitro model. | 2008-07-03 |
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| Protective effect of the natural product, chaetoglobosin K, on lindane- and dieldrin-induced changes in astroglia: identification of activated signaling pathways. | 2008-06 |
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| Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008-04 |
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| Xenoestrogens modulate vascular endothelial growth factor secretion in breast cancer cells through an estrogen receptor-dependent mechanism. | 2008-02 |
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| Dieldrin exposure induces oxidative damage in the mouse nigrostriatal dopamine system. | 2007-04 |
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| Occupational exposure to organochlorine insecticides and cancer incidence in the Agricultural Health Study. | 2007-02-01 |
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| Xenoestrogens are potent activators of nongenomic estrogenic responses. | 2007-02 |
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| Dieldrin resistance in the malaria vector Anopheles gambiae in Ghana. | 2006-09 |
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| Reversibility of promoter induced hepatic focal lesion growth in mice. | 1996-07 |
|
| Single-stranded DNA conformation polymorphism at the Rdl locus in Hypothenemus hampei (Coleoptera: Scolytidae). | 1996-02 |
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| Oxidative stress in fish exposed to model xenobiotics. Oxidatively modified forms of Cu,Zn-superoxide dismutase as potential biomarkers. | 1995-12-22 |
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| The species specificity of dieldrin- or phenobarbital- induced hepatocarcinogenesis: case studies with implications for human health risk assessment. | 1995 |
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| Drosophila GABA-gated chloride channel: modified [3H]EBOB binding site associated with Ala-->Ser or Gly mutants of Rdl subunit. | 1995 |
|
| Changes in gap-junction permeability, phosphorylation, and number mediated by phorbol ester and non-phorbol-ester tumor promoters in rat liver epithelial cells. | 1994-08 |
|
| A single-amino acid substitution in a gamma-aminobutyric acid subtype A receptor locus is associated with cyclodiene insecticide resistance in Drosophila populations. | 1993-03-01 |
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| Effects of environmentally encountered epoxides on mouse liver epoxide-metabolizing enzymes. | 1991-06-01 |
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| Gene mapping and cross-resistance in cyclodiene insecticide-resistant Drosophila melanogaster (Mg.). | 1991-02 |
|
| Strain and species effects on the inhibition of hepatocyte intercellular communication by liver tumor promoters. | 1987-08 |
|
| Chlorinated hydrocarbon pesticides and amygdaloid kindling. | 1985-05-01 |
|
| Dieldrin and diazinon resistance in populations of the Australian sheep blowfly, Lucilia cuprina, from sheep-grazing areas and rubbish tips. | 1984 |
|
| Comparison of the promoting effects of various agents in induction of preneoplastic lesions in rat liver. | 1983-04 |
|
| Modification of hexachlorophene toxicity by dieldrin and aroclor 1254. | 1974-09 |
Sample Use Guides
As mitochondrial dysfunction is involved in the etiology of Parkinson's disease, there was study aimed to determine whether dieldrin (DLD) impaired mitochondrial bioenergetics in dopaminergic cells. Rat immortalized dopaminergic N27 cells were treated for 24 or 48h with one dose of either a solvent control, 2.5, 25, or 250 μM DLD. Dopaminergic cells treated with 250 μM DLD showed increased Casp3/7 activity at 24 and 48h. DLD also caused a dose dependent reduction in cell viability of 25-30 % over 24 h. No significant effects on cell viability, apoptosis, nor cytotoxicity were detected at 24 or 48 h with 2.5 μM DLD. Following a 24 h exposure to 2.5 and 25 μM DLD, viable cells were subjected to a mitochondrial stress test using the Seahorse XFe24 Extracellular Flux Analyzer. Following three independent experiments conducted for rigor, dopaminergic cells that were treated with 2.5 and 25 μM DLD consistently showed a reduction in maximum respiration and spare capacity compared to the control group. Molecular responses were measured to determine mechanisms of DLD-induced mitochondrial dysfunction.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:27:23 GMT 2025
by
admin
on
Mon Mar 31 19:27:23 GMT 2025
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| Record UNII |
I0246D2ZS0
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
45001
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34696
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CHEMBL1873703
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I0246D2ZS0
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DTXSID9020453
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322
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8934
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60-57-1
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C169908
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SUB07106MIG
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m4384
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D004026
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Dieldrin
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856
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dieldrin
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969491
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100000082923
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200-484-5
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Dieldrin (see Dieldrin, and aldrin metabolized to dieldrin)
Created by
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METABOLITE -> PARENT |
aldrin-transdiol is dieldrin metabolite suggested as active neurotoxic form
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ACTIVE MOIETY |
