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 |
|---|---|---|
| Mitochondrial dysfunction increases expression of endothelin-1 and induces apoptosis through caspase-3 activation in rat cardiomyocytes in vitro. | 2000 Nov |
|
| Mitochondrial-derived oxidants and quartz activation of chemokine gene expression. | 2001 |
|
| Dopaminergic cell death induced by MPP(+), oxidant and specific neurotoxicants shares the common molecular mechanism. | 2001 Feb |
|
| Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism. | 2001 Jul |
|
| Role of mitochondrial oxidant generation in endothelial cell responses to hypoxia. | 2002 Apr 1 |
|
| An in vitro model of Parkinson's disease: linking mitochondrial impairment to altered alpha-synuclein metabolism and oxidative damage. | 2002 Aug 15 |
|
| Proteasome inhibitors stimulate activator protein-1 pathway via reactive oxygen species production. | 2002 Aug 28 |
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| Distinct role for microglia in rotenone-induced degeneration of dopaminergic neurons. | 2002 Feb 1 |
|
| Expression of mutant alpha-synucleins enhances dopamine transporter-mediated MPP+ toxicity in vitro. | 2002 Jul 19 |
|
| 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 |
|
| Inhibitors of mitochondrial complex I attenuate the accumulation of hypoxia-inducible factor-1 during hypoxia in Hep3B cells. | 2002 May |
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| Hypoxic but not anoxic stabilization of HIF-1alpha requires mitochondrial reactive oxygen species. | 2002 Nov |
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| The pesticide rotenone induces caspase-3-mediated apoptosis in ventral mesencephalic dopaminergic neurons. | 2003 Nov |
|
| Hypoxia and stretch regulate intercellular communication in vascular smooth muscle cells through reactive oxygen species formation. | 2003 Oct 1 |
|
| Abnormal alpha-synuclein interactions with Rab proteins in alpha-synuclein A30P transgenic mice. | 2004 Apr |
|
| Rotenone induces non-specific central nervous system and systemic toxicity. | 2004 Apr |
|
| Trichomonas hydrogenosomes contain the NADH dehydrogenase module of mitochondrial complex I. | 2004 Dec 2 |
|
| Protective effect of 1-methyl-1,2,3,4-tetrahydroisoquinoline against dopaminergic neurodegeneration in the extrapyramidal structures produced by intracerebral injection of rotenone. | 2004 Jun |
|
| Rotenone-induced apoptosis is mediated by p38 and JNK MAP kinases in human dopaminergic SH-SY5Y cells. | 2004 May |
|
| Sensitivity of zebrafish to environmental toxins implicated in Parkinson's disease. | 2004 Nov-Dec |
|
| Small interfering RNA targeting the PINK1 induces apoptosis in dopaminergic cells SH-SY5Y. | 2005 Dec 2 |
|
| Similar patterns of mitochondrial vulnerability and rescue induced by genetic modification of alpha-synuclein, parkin, and DJ-1 in Caenorhabditis elegans. | 2005 Dec 30 |
|
| Role of mitochondria in the regulation of hypoxia-inducible factor-1alpha in the rat carotid body glomus cells. | 2005 Jul |
|
| In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. | 2005 Mar-Apr |
|
| The mitochondrial complex I inhibitor rotenone triggers a cerebral tauopathy. | 2005 Nov |
|
| Mitochondrial manganese-superoxide dismutase expression in ovarian cancer: role in cell proliferation and response to oxidative stress. | 2005 Nov 25 |
|
| Hypertonic induction of COX-2 in collecting duct cells by reactive oxygen species of mitochondrial origin. | 2005 Oct 14 |
|
| Early environmental origins of neurodegenerative disease in later life. | 2005 Sep |
|
| Protective effect of melatonin on rotenone plus Ca2+-induced mitochondrial oxidative stress and PC12 cell death. | 2005 Sep-Oct |
|
| Metallothionein isoform 2A expression is inducible and protects against ROS-mediated cell death in rotenone-treated HeLa cells. | 2006 Apr 15 |
|
| Activation of group III metabotropic glutamate receptors attenuates rotenone toxicity on dopaminergic neurons through a microtubule-dependent mechanism. | 2006 Apr 19 |
|
| Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells. | 2006 Aug |
|
| Mitochondrial disease activates transcripts of the unfolded protein response and cell cycle and inhibits vesicular secretion and oligodendrocyte-specific transcripts. | 2006 Aug |
|
| Copper-induced stimulation of extracellular signal-regulated kinase in trout hepatocytes: the role of reactive oxygen species, Ca2+, and cell energetics and the impact of extracellular signal-regulated kinase signaling on apoptosis and necrosis. | 2006 Aug |
|
| Thioredoxin-ASK1 complex levels regulate ROS-mediated p38 MAPK pathway activity in livers of aged and long-lived Snell dwarf mice. | 2006 Feb |
|
| A delivery strategy for rotenone microspheres in an animal model of Parkinson's disease. | 2006 Feb |
|
| The regulation of rotenone-induced inflammatory factor production by ATP-sensitive potassium channel expressed in BV-2 cells. | 2006 Feb 13 |
|
| Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase. | 2006 Jul |
|
| Proteomic identification of a stress protein, mortalin/mthsp70/GRP75: relevance to Parkinson disease. | 2006 Jul |
|
| L-deprenyl protects against rotenone-induced, oxidative stress-mediated dopaminergic neurodegeneration in rats. | 2006 Jul |
|
| p44/42 MAP kinase and c-Jun N-terminal kinase contribute to the up-regulation of caspase-3 in manganese-induced apoptosis in PC12 cells. | 2006 Jul 12 |
|
| Mitochondrial electron transport in models of neuropathic and inflammatory pain. | 2006 Mar |
|
| Susceptibility to rotenone is increased in neurons from parkin null mice and is reduced by minocycline. | 2006 May |
|
| Intersecting pathways to neurodegeneration in Parkinson's disease: effects of the pesticide rotenone on DJ-1, alpha-synuclein, and the ubiquitin-proteasome system. | 2006 May |
|
| Mitochondrial reactive oxygen species contribute to high NaCl-induced activation of the transcription factor TonEBP/OREBP. | 2006 May |
|
| Mitochondrial activity is modulated by TNFalpha and IL-1beta in normal human chondrocyte cells. | 2006 Oct |
|
| Rotenone induces cell death in primary dopaminergic culture by increasing ROS production and inhibiting mitochondrial respiration. | 2006 Sep |
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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| Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
71003
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NCI_THESAURUS |
C737
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03L9OT429T
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6758
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DTXSID6021248
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201-501-9
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1366666
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1762
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D012402
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C76087
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26258
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DB11457
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03L9OT429T
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SUB130991
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m9673
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28201
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83-79-4
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100000156877
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ROTENONE
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rotenone
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SUBSTANCE RECORD
