Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H22O6 |
| Molecular Weight | 394.4172 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12COC3=CC(OC)=C(OC)C=C3[C@]1([H])C(=O)C4=C(O2)C5=C(O[C@H](C5)C(C)=C)C=C4
InChI
InChIKey=JUVIOZPCNVVQFO-HBGVWJBISA-N
InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
Rotenone is a selective, non-specific botanical insecticide with some acaricidal properties. Rotenone is used in home gardens for insect control, for lice and tick control on pets, and for fish eradications as part of water body management. Rotenone is a rotenoid plant extract obtained from such species as barbasco, cub, haiari, nekoe, and timbo. These plants are members of the pea (Leguminosae) family. Rotenone-containing extracts are taken from the roots, seeds, and leaves of the various plants. This chemical has been used in one form or another as a crop insecticide since 1848 and has been recognized as a registered pesticide in the United States under the Federal Insecticide Fungicide Rodenticide Act (FIFRA) since 1947. Rotenone has also been found to also have properties of a pescicide where it is generally used to rid environments of non-native predatory fish species. Rotenone is a commonly used neurotoxin to produce in vivo and in vitro Parkinson's disease models. Rotenone is the classical inhibitor of NADH: ubiquinone oxidoreductase.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22970265 | https://www.ncbi.nlm.nih.gov/pubmed/14766796
Curator's Comment: Rotenone is lipophilic and can cross the blood–brain barrier. Rotenone is a commonly used neurotoxin to produce in vivo and in vitro Parkinson's disease models.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 4.4 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | PESTENE Approved UseFor poultry, pigeons and pigs. For the treatment of Round Worms (Ascaridia Galli) in Poultry (Ascaridia columbae) in Pigeons; Round Worms (Ascaris suum) and Nodule Worms (Oesophagostomum spp) in Pigs. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Rotenone and pyruvate prevent the tert-butylhydroperoxide-induced necrosis of U937 cells and allow them to proliferate. | 1999 Aug 20 |
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| Diminished energy metabolism and enhanced apoptosis in livers of B6C3F1 mice treated with the antihepatocarcinogen rotenone. | 1999 Nov |
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| Sodium arsenate induces overproduction of interleukin-1alpha in murine keratinocytes: role of mitochondria. | 1999 Nov |
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| Inhibition of mitochondrial function in HL60 cells is associated with an increased apoptosis and expression of CD14. | 1999 Sep 24 |
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| Interleukin 1-induced cyclooxygenase and nitric oxide synthase gene expression in the rat dorsal root ganglia is modulated by antioxidants. | 2001 |
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| Endothelin-1 production is enhanced by rotenone, a mitochondrial complex I inhibitor, in cultured rat cardiomyocytes. | 2001 Dec |
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| Pesticides directly accelerate the rate of alpha-synuclein fibril formation: a possible factor in Parkinson's disease. | 2001 Jul 6 |
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| Role of mitochondrial oxidant generation in endothelial cell responses to hypoxia. | 2002 Apr 1 |
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| An in vitro model of Parkinson's disease: linking mitochondrial impairment to altered alpha-synuclein metabolism and oxidative damage. | 2002 Aug 15 |
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| Proteasome inhibitors stimulate activator protein-1 pathway via reactive oxygen species production. | 2002 Aug 28 |
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| Endoplasmic reticulum stress and the unfolded protein response in cellular models of Parkinson's disease. | 2002 Dec 15 |
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| The fetal and neonatal brain protein neuronatin protects PC12 cells against certain types of toxic insult. | 2002 Jun 30 |
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| Activation of matrix metalloproteinase-2 by overexpression of manganese superoxide dismutase in human breast cancer MCF-7 cells involves reactive oxygen species. | 2002 Jun 7 |
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| Hypoxic but not anoxic stabilization of HIF-1alpha requires mitochondrial reactive oxygen species. | 2002 Nov |
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| Rotenone destroys dopaminergic neurons and induces parkinsonian symptoms in rats. | 2002 Oct 17 |
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| Human mitochondrial thioredoxin. Involvement in mitochondrial membrane potential and cell death. | 2002 Sep 6 |
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| Reversal of Bcl-2-mediated resistance of the EW36 human B-cell lymphoma cell line to arsenite- and pesticide-induced apoptosis by PK11195, a ligand of the mitochondrial benzodiazepine receptor. | 2003 Jul |
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| Mitochondrial complex I inhibitor rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. | 2003 Mar 7 |
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| NF-E2-related factor-2 mediates neuroprotection against mitochondrial complex I inhibitors and increased concentrations of intracellular calcium in primary cortical neurons. | 2003 Sep 26 |
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| Rotenone, a mitochondrial electron transport inhibitor, ameliorates ischemia-reperfusion-induced intestinal mucosal damage in rats. | 2004 |
|
| Abnormal alpha-synuclein interactions with Rab proteins in alpha-synuclein A30P transgenic mice. | 2004 Apr |
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| Reactive oxygen species amplify protein kinase C signaling in high glucose-induced fibronectin expression by human peritoneal mesothelial cells. | 2004 Apr |
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| Trichomonas hydrogenosomes contain the NADH dehydrogenase module of mitochondrial complex I. | 2004 Dec 2 |
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| Mutation in mitochondrial complex I ND6 subunit is associated with defective response to hypoxia in human glioma cells. | 2004 Jul 12 |
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| Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver. | 2004 Jun 1 |
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| 1-Benzyl-1,2,3,4-tetrahydroisoquinoline, a Parkinsonism-inducing endogenous toxin, increases alpha-synuclein expression and causes nuclear damage in human dopaminergic cells. | 2004 May 15 |
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| Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells. | 2004 Nov |
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| Sensitivity of zebrafish to environmental toxins implicated in Parkinson's disease. | 2004 Nov-Dec |
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| Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats. | 2005 Jan |
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| Redox regulation of p38 MAPK activation and expression of ICAM-1 and heme oxygenase-1 in human alveolar epithelial (A549) cells. | 2005 Jan-Feb |
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| Role of mitochondria in the regulation of hypoxia-inducible factor-1alpha in the rat carotid body glomus cells. | 2005 Jul |
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| Mitochondrial manganese-superoxide dismutase expression in ovarian cancer: role in cell proliferation and response to oxidative stress. | 2005 Nov 25 |
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| Hypertonic induction of COX-2 in collecting duct cells by reactive oxygen species of mitochondrial origin. | 2005 Oct 14 |
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| Early environmental origins of neurodegenerative disease in later life. | 2005 Sep |
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| Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells. | 2006 Aug |
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| Mitochondrial disease activates transcripts of the unfolded protein response and cell cycle and inhibits vesicular secretion and oligodendrocyte-specific transcripts. | 2006 Aug |
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| Activation of mitochondrial ATP-sensitive potassium channels improves rotenone-related motor and neurochemical alterations in rats. | 2006 Feb |
|
| The regulation of rotenone-induced inflammatory factor production by ATP-sensitive potassium channel expressed in BV-2 cells. | 2006 Feb 13 |
|
| Mitochondrial electron transport in models of neuropathic and inflammatory pain. | 2006 Mar |
Patents
Sample Use Guides
Rats: Intraperitoneal injection of rotenone (2 mg/kg/day) to Wistar rats produced typical PD symptoms.
Route of Administration:
Intraperitoneal
In human induced pluripotent stem cells Rotenone was found to induce the activation of Nrf2 signaling particularly at the highest tested concentration (100 nM), as shown by Nrf2 nuclear translocation and the up-regulation of the Nrf2-downstream antioxidant enzymes, NQO1 and SRXN1.
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EPA PESTICIDE CODE |
71003
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NCI_THESAURUS |
C737
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100000156877
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ROTENONE
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rotenone
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SUBSTANCE RECORD
