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
COC1=CC2=C(C=C1OC)[C@H]3[C@@H](CO2)OC4=C5C[C@@H](OC5=CC=C4C3=O)C(C)=C
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
| Molecular Formula | C23H22O6 |
| Molecular Weight | 394.4172 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 activity is modulated by TNFalpha and IL-1beta in normal human chondrocyte cells. | 2006-10 |
|
| Rotenone induces cell death in primary dopaminergic culture by increasing ROS production and inhibiting mitochondrial respiration. | 2006-09 |
|
| Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells. | 2006-08 |
|
| Mitochondrial disease activates transcripts of the unfolded protein response and cell cycle and inhibits vesicular secretion and oligodendrocyte-specific transcripts. | 2006-08 |
|
| 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. | 2006-08 |
|
| 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. | 2006-07-12 |
|
| Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase. | 2006-07 |
|
| Proteomic identification of a stress protein, mortalin/mthsp70/GRP75: relevance to Parkinson disease. | 2006-07 |
|
| L-deprenyl protects against rotenone-induced, oxidative stress-mediated dopaminergic neurodegeneration in rats. | 2006-07 |
|
| Parkin protects against mitochondrial toxins and beta-amyloid accumulation in skeletal muscle cells. | 2006-05-05 |
|
| Susceptibility to rotenone is increased in neurons from parkin null mice and is reduced by minocycline. | 2006-05 |
|
| Intersecting pathways to neurodegeneration in Parkinson's disease: effects of the pesticide rotenone on DJ-1, alpha-synuclein, and the ubiquitin-proteasome system. | 2006-05 |
|
| Mitochondrial reactive oxygen species contribute to high NaCl-induced activation of the transcription factor TonEBP/OREBP. | 2006-05 |
|
| Activation of group III metabotropic glutamate receptors attenuates rotenone toxicity on dopaminergic neurons through a microtubule-dependent mechanism. | 2006-04-19 |
|
| Metallothionein isoform 2A expression is inducible and protects against ROS-mediated cell death in rotenone-treated HeLa cells. | 2006-04-15 |
|
| Mitochondrial electron transport in models of neuropathic and inflammatory pain. | 2006-03 |
|
| The regulation of rotenone-induced inflammatory factor production by ATP-sensitive potassium channel expressed in BV-2 cells. | 2006-02-13 |
|
| Thioredoxin-ASK1 complex levels regulate ROS-mediated p38 MAPK pathway activity in livers of aged and long-lived Snell dwarf mice. | 2006-02 |
|
| A delivery strategy for rotenone microspheres in an animal model of Parkinson's disease. | 2006-02 |
|
| Activation of mitochondrial ATP-sensitive potassium channels improves rotenone-related motor and neurochemical alterations in rats. | 2006-02 |
|
| Similar patterns of mitochondrial vulnerability and rescue induced by genetic modification of alpha-synuclein, parkin, and DJ-1 in Caenorhabditis elegans. | 2005-12-30 |
|
| Effect of fraxetin on antioxidant defense and stress proteins in human neuroblastoma cell model of rotenone neurotoxicity. Comparative study with myricetin and N-acetylcysteine. | 2005-12-15 |
|
| Small interfering RNA targeting the PINK1 induces apoptosis in dopaminergic cells SH-SY5Y. | 2005-12-02 |
|
| Mitochondrial manganese-superoxide dismutase expression in ovarian cancer: role in cell proliferation and response to oxidative stress. | 2005-11-25 |
|
| The mitochondrial complex I inhibitor rotenone triggers a cerebral tauopathy. | 2005-11 |
|
| Hypertonic induction of COX-2 in collecting duct cells by reactive oxygen species of mitochondrial origin. | 2005-10-14 |
|
| Early induction of calpains in rotenone-mediated neuronal apoptosis. | 2005-09-14 |
|
| Mitochondrial reactive oxygen species and c-Src play a critical role in hypoxic response in vascular smooth muscle cells. | 2005-09-01 |
|
| Early environmental origins of neurodegenerative disease in later life. | 2005-09 |
|
| Protective effect of melatonin on rotenone plus Ca2+-induced mitochondrial oxidative stress and PC12 cell death. | 2005-08-24 |
|
| Estrogen-induced G1/S transition of G0-arrested estrogen-dependent breast cancer cells is regulated by mitochondrial oxidant signaling. | 2005-07-21 |
|
| PACAP protects neuronal differentiated PC12 cells against the neurotoxicity induced by a mitochondrial complex I inhibitor, rotenone. | 2005-07-18 |
|
| Role of mitochondria in the regulation of hypoxia-inducible factor-1alpha in the rat carotid body glomus cells. | 2005-07 |
|
| Sleep disturbances in the rotenone animal model of Parkinson disease. | 2005-05-03 |
|
| Systematic administration of iptakalim, an ATP-sensitive potassium channel opener, prevents rotenone-induced motor and neurochemical alterations in rats. | 2005-05-01 |
|
| In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. | 2005-03-31 |
|
| Rotenone induces oxidative stress and dopaminergic neuron damage in organotypic substantia nigra cultures. | 2005-03-24 |
|
| Inducers of oxidative stress block ciliary neurotrophic factor activation of Jak/STAT signaling in neurons. | 2005-03 |
|
| Hyperglycemia activates JAK2 signaling pathway in human failing myocytes via angiotensin II-mediated oxidative stress. | 2005-02 |
|
| Redox regulation of p38 MAPK activation and expression of ICAM-1 and heme oxygenase-1 in human alveolar epithelial (A549) cells. | 2005-01-15 |
|
| Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats. | 2005-01 |
|
| Trichomonas hydrogenosomes contain the NADH dehydrogenase module of mitochondrial complex I. | 2004-12-02 |
|
| Chronic exposure to rotenone models sporadic Parkinson's disease in Drosophila melanogaster. | 2004-12-01 |
|
| Lipopolysaccharide induces matrix metalloproteinase-9 expression via a mitochondrial reactive oxygen species-p38 kinase-activator protein-1 pathway in Raw 264.7 cells. | 2004-12-01 |
|
| Rotenone induces apoptosis via activation of bad in human dopaminergic SH-SY5Y cells. | 2004-12 |
|
| Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells. | 2004-11 |
|
| Mutation in mitochondrial complex I ND6 subunit is associated with defective response to hypoxia in human glioma cells. | 2004-07-12 |
|
| Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver. | 2004-06-01 |
|
| Sensitivity of zebrafish to environmental toxins implicated in Parkinson's disease. | 2004-04-14 |
|
| Rotenone, a mitochondrial electron transport inhibitor, ameliorates ischemia-reperfusion-induced intestinal mucosal damage in rats. | 2004 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:46:21 GMT 2025
by
admin
on
Mon Mar 31 17:46:21 GMT 2025
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| Record UNII |
03L9OT429T
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
71003
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NCI_THESAURUS |
C737
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1366666
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1762
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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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