This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Rotenone
- DrugBank Accession Number
- DB11457
- Background
Rotenone is an isoflavone compound that naturally occurs in the jicama vine plant as well as many Fabaceae plants. It has broad spectrum insecticide and pesticide activity and is also toxic to fish.
- Type
- Small Molecule
- Groups
- Vet approved
- Structure
Structure for Rotenone (DB11457)
- Weight
- Average: 394.4172
Monoisotopic: 394.141638436 - Chemical Formula
- C23H22O6
- Synonyms
- (−)-cis-rotenone
- (−)-rotenone
- (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one
- [2R-(2α,6aα,12aα)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6aH)-one
- 5'β-rotenone
- Dactinol
- Tubatoxin
- External IDs
- NSC-26258
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Isoflavonoids
- Sub Class
- Rotenoids
- Direct Parent
- Rotenones
- Alternative Parents
- 8-prenylated isoflavanones / Chromones / Coumarans / Aryl alkyl ketones / Anisoles / Alkyl aryl ethers / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-benzopyran / 8-prenylated isoflavanone / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Benzenoid / Benzopyran / Chromane
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic heteropentacyclic compound, rotenones (CHEBI:28201) / rotenones, Rotenoid flavonoids, Pesticides (C07593) / Rotenoid flavonoids (LMPK12060007)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 03L9OT429T
- CAS number
- 83-79-4
- InChI Key
- JUVIOZPCNVVQFO-HBGVWJBISA-N
- InChI
- 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
- IUPAC Name
- (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one
- SMILES
- [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C
References
- General References
- Yang SP, Yu XB, Huang JG, Xu HH: Rotenone alpha-oxime. Acta Crystallogr C. 2003 Jul;59(Pt 7):o392-3. Epub 2003 Jun 20. [Article]
- OLIVER WT, ROE CK: Rotenone poisoning of swine. J Am Vet Med Assoc. 1957 May 1;130(9):410-1. [Article]
- SANTI R, TOTH CE: TOXICOLOGY OF ROTENONE. Farmaco Sci. 1965 Apr;20:270-9. [Article]
- Santi R, Ferrari M, Toth E: Pharmacological properties of rotenone. Farmaco Sci. 1966 Oct;21(10):689-703. [Article]
- BRYAN JT, LINCOLN WR: Determination of rotenone in pharmaceuticals. J Am Pharm Assoc Am Pharm Assoc. 1959 Jun;48(6):330-2. [Article]
- DANZEL L: [Derris and other rotenone plants]. Prod Pharm. 1951 Oct;6(10):487-9. [Article]
- Gosalvez M: Carcinogenesis with the insecticide rotenone. Life Sci. 1983 Feb 21;32(8):809-16. [Article]
- Gosalvez M, Diaz-Gil JJ: Rotenone: a possible environmental carcinogen? Eur J Cancer. 1978 Dec;14(12):1403-4. [Article]
- Acree F Jr, Jacobson M, Haller HL: AMORPHA FRUTICOSA CONTAINS NO ROTENONE. Science. 1944 Feb 4;99(2562):99-100. [Article]
- Tanner CM, Kamel F, Ross GW, Hoppin JA, Goldman SM, Korell M, Marras C, Bhudhikanok GS, Kasten M, Chade AR, Comyns K, Richards MB, Meng C, Priestley B, Fernandez HH, Cambi F, Umbach DM, Blair A, Sandler DP, Langston JW: Rotenone, paraquat, and Parkinson's disease. Environ Health Perspect. 2011 Jun;119(6):866-72. doi: 10.1289/ehp.1002839. Epub 2011 Jan 26. [Article]
- Khar A, Ali AM, Begum Z, Pardhasaradhi BV, Varalakshmi C: Induction of apoptosis in AK-5 cells by rotenone involves participation of caspases. Indian J Biochem Biophys. 1999 Apr;36(2):77-81. [Article]
- Tapias V, Cannon JR, Greenamyre JT: Melatonin treatment potentiates neurodegeneration in a rat rotenone Parkinson's disease model. J Neurosci Res. 2010 Feb 1;88(2):420-7. doi: 10.1002/jnr.22201. [Article]
- Newhouse K, Hsuan SL, Chang SH, Cai B, Wang Y, Xia Z: Rotenone-induced apoptosis is mediated by p38 and JNK MAP kinases in human dopaminergic SH-SY5Y cells. Toxicol Sci. 2004 May;79(1):137-46. Epub 2004 Feb 19. [Article]
- Cao S, Schilling JK, Miller JS, Andriantsiferana R, Rasamison VE, Kingston DG: Cytotoxic compounds from Mundulea chapelieri from the Madagascar Rainforest. J Nat Prod. 2004 Mar;67(3):454-6. [Article]
- Testa CM, Sherer TB, Greenamyre JT: Rotenone induces oxidative stress and dopaminergic neuron damage in organotypic substantia nigra cultures. Brain Res Mol Brain Res. 2005 Mar 24;134(1):109-18. Epub 2005 Jan 6. [Article]
- Morikawa T, Xu F, Matsuda H, Yoshikawa M: Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand. Chem Pharm Bull (Tokyo). 2006 Nov;54(11):1530-4. [Article]
- Meurers BH, Zhu C, Fernagut PO, Richter F, Hsia YC, Fleming SM, Oh M, Elashoff D, Dicarlo CD, Seaman RL, Chesselet MF: Low dose rotenone treatment causes selective transcriptional activation of cell death related pathways in dopaminergic neurons in vivo. Neurobiol Dis. 2009 Feb;33(2):182-92. doi: 10.1016/j.nbd.2008.10.001. Epub 2008 Oct 26. [Article]
- Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
- External Links
- Human Metabolome Database
- HMDB0034436
- KEGG Compound
- C07593
- PubChem Compound
- 6758
- PubChem Substance
- 347827979
- ChemSpider
- 6500
- BindingDB
- 50135527
- 1366666
- ChEBI
- 28201
- ChEMBL
- CHEMBL429023
- ZINC
- ZINC000003860715
- PDBe Ligand
- 970
- Wikipedia
- Rotenone
- PDB Entries
- 6zkk / 6zkl / 6zkm / 6zkn / 7v31 / 7v33 / 7vbz / 7vyf / 7w1t / 7w1u … show 3 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0129 mg/mL ALOGPS logP 2.3 ALOGPS logP 3.32 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 13.99 Chemaxon pKa (Strongest Basic) -4.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 63.22 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 105.71 m3·mol-1 Chemaxon Polarizability 42.07 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 211.2084632 predictedDarkChem Lite v0.1.0 [M-H]- 210.9345632 predictedDarkChem Lite v0.1.0 [M-H]- 211.3240632 predictedDarkChem Lite v0.1.0 [M-H]- 210.8109632 predictedDarkChem Lite v0.1.0 [M-H]- 210.9455632 predictedDarkChem Lite v0.1.0 [M-H]- 193.75304 predictedDeepCCS 1.0 (2019) [M+H]+ 210.9375632 predictedDarkChem Lite v0.1.0 [M+H]+ 197.9013769 predictedDarkChem Standard v0.1.0 [M+H]+ 211.6196632 predictedDarkChem Lite v0.1.0 [M+H]+ 210.9054632 predictedDarkChem Lite v0.1.0 [M+H]+ 210.8235632 predictedDarkChem Lite v0.1.0 [M+H]+ 196.1486 predictedDeepCCS 1.0 (2019) [M+Na]+ 211.0973632 predictedDarkChem Lite v0.1.0 [M+Na]+ 202.5143216 predictedDarkChem Standard v0.1.0 [M+Na]+ 211.2483632 predictedDarkChem Lite v0.1.0 [M+Na]+ 210.8311632 predictedDarkChem Lite v0.1.0 [M+Na]+ 210.9672632 predictedDarkChem Lite v0.1.0 [M+Na]+ 202.06113 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 18:54 / Updated at June 12, 2020 16:53