Tetramethrin
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Basic Info
| Common Name | Tetramethrin(F04044) |
| 2D Structure | |
| Description | Tetramethrin is a potent synthetic insecticide in the pyrethroid (type 1) family. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. (L811) |
| FRCD ID | F04044 |
| CAS Number | 7696-12-0 |
| PubChem CID | 83975 |
| Formula | C19H25NO4 |
| IUPAC Name | (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate |
| InChI Key | CXBMCYHAMVGWJQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3 |
| Canonical SMILES | CC(=CC1C(C1(C)C)C(=O)OCN2C(=O)C3=C(C2=O)CCCC3)C |
| Isomeric SMILES | CC(=CC1C(C1(C)C)C(=O)OCN2C(=O)C3=C(C2=O)CCCC3)C |
| Synonyms |
7696-12-0
Tetramethrin
Phthalthrin
Neo-pynamin
Neopinamin
Neopinamine
Bioneopynamin
Insectol
Neopynamin forte
Py-Kill
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Isoindoles and derivatives |
| Subclass | Isoindolines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Isoindolones |
| Alternative Parents |
|
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Bicyclic monoterpenoid - Isoindolone - Monoterpenoid - Isoindole - Maleimide - Cyclopropanecarboxylic acid or derivatives - Carboxylic acid imide, n-substituted - Pyrroline - Carboxylic acid imide - Dicarboximide - Carboxylic acid ester - Lactam - Azacycle - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organooxygen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Organic nitrogen compound - Organonitrogen compound - Carbonyl group - Hydrocarbon derivative - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 331.412 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 639 |
| Monoisotopic Mass | 331.178 |
| Exact Mass | 331.178 |
| XLogP | 4.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9314 |
| Human Intestinal Absorption | HIA+ | 0.9786 |
| Caco-2 Permeability | Caco2- | 0.5213 |
| P-glycoprotein Substrate | Non-substrate | 0.5557 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5156 |
| Inhibitor | 0.6363 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7839 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8045 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8814 |
| CYP450 2D6 Substrate | Non-substrate | 0.8173 |
| CYP450 3A4 Substrate | Substrate | 0.7068 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6350 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7968 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9017 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6442 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7924 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5087 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9644 |
| Non-inhibitor | 0.9117 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.8742 |
| Fish Toxicity | High FHMT | 0.9783 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9440 |
| Honey Bee Toxicity | High HBT | 0.7534 |
| Biodegradation | Not ready biodegradable | 0.8649 |
| Acute Oral Toxicity | III | 0.7731 |
| Carcinogenicity (Three-class) | Non-required | 0.4940 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1783 | LogS |
| Caco-2 Permeability | 1.2564 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8612 | LD50, mol/kg |
| Fish Toxicity | 0.5212 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3874 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Pyrethroid insecticides in wild bird eggs from a World Heritage Listed Park: Acase study in Doñana National Park (Spain). | Environ Pollut | 2017 Sep | 28551562 |
| Determinants of children's exposure to pyrethroid insecticides in western France. | Environ Int | 2017 Jul | 28453973 |
| Photosensitizers in the fight against ticks: safranin as a novel photodynamicfluorescent acaricide to control the camel tick Hyalomma dromedarii (Ixodidae). | Parasitol Res | 2016 Oct | 27230018 |
| Enantiomeric-selective determination of pyrethroids: application to humansamples. | Anal Bioanal Chem | 2015 Jan | 25027720 |
| Two-step microextraction combined with high performance liquid chromatographicanalysis of pyrethroids in water and vegetable samples. | Talanta | 2014 Mar | 24468372 |
| Multiresidue pesticide analysis of botanical dietary supplements using salt-outacetonitrile extraction, solid-phase extraction cleanup column, and gaschromatography-triple quadrupole mass spectrometry. | Anal Chem | 2013 May 7 | 23534560 |
| Determination of six pyrethroid insecticides in fruit juice samples usingdispersive liquid-liquid microextraction combined with high performance liquidchromatography. | Talanta | 2012 Jan 15 | 22265489 |
| Comparison of the performance of conventional, temperature-controlled, andultrasound-assisted ionic liquid dispersive liquid-liquid microextractioncombined with high-performance liquid chromatography in analyzing pyrethroidpesticides in honey samples. | J Chromatogr A | 2011 Sep 23 | 21862027 |
| Simultaneous determination of 16 pyrethroid residues in tea samples using gaschromatography and ion trap mass spectrometry. | J Chromatogr Sci | 2010 Oct | 20875241 |
| Acute toxicity to zebrafish of two organophosphates and four pyrethroids andtheir binary mixtures. | Pest Manag Sci | 2010 Jan | 19728319 |
| Identification and quantitation of pyrethroid pesticide residues in vegetables bysolid-phase extraction and liquid chromatography/electrospray ionization ion trapmass spectrometry. | Rapid Commun Mass Spectrom | 2007 | 17510928 |
| Assessing estrogenic activity of pyrethroid insecticides using in vitrocombination assays. | J Reprod Dev | 2004 Apr | 15118252 |
| Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection. | J AOAC Int | 2003 Nov-Dec | 14979708 |
| Characterisation of gene expression patterns in 22RV1 cells for determination of environmental androgenic/antiandrogenic compounds. | J Steroid Biochem Mol Biol | 2003 Feb | 12711008 |
| Multiresidue liquid chromatographic method for simultaneous determination ofpyrethroid insecticides in fruits and vegetables. | J AOAC Int | 1995 Nov-Dec | 8664585 |
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with PSGL1/SELPLG. May have a role in capillary morphogenesis.
- Gene Name:
- SELE
- Uniprot ID:
- P16581
- Molecular Weight:
- 66654.575 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Metal ion binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium.
- Gene Name:
- ATP2C2
- Uniprot ID:
- O75185
- Molecular Weight:
- 103186.475 Da
- Mechanism of Action:
- This pyrethroid inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN1A
- Uniprot ID:
- P35498
- Molecular Weight:
- 228969.49 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
- Gene Name:
- SCN10A
- Uniprot ID:
- Q9Y5Y9
- Molecular Weight:
- 220623.605 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Also involved, with the contribution of the receptor tyrosine kinase NTRK2, in rapid BDNF-evoked neuronal depolarization.
- Gene Name:
- SCN11A
- Uniprot ID:
- Q9UI33
- Molecular Weight:
- 204919.66 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN2A
- Uniprot ID:
- Q99250
- Molecular Weight:
- 227972.64 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- S100 protein binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the translocation of calcium from the cytosol to the sarcoplasmic reticulum lumen. Isoform 2 is involved in the regulation of the contraction/relaxation cycle.
- Gene Name:
- ATP2A2
- Uniprot ID:
- P16615
- Molecular Weight:
- 114755.765 Da
- Mechanism of Action:
- This pyrethroid inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. This sodium channel may be present in both denervated and innervated skeletal muscle.
- Gene Name:
- SCN4A
- Uniprot ID:
- P35499
- Molecular Weight:
- 208059.175 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN7A
- Uniprot ID:
- Q01118
- Molecular Weight:
- 193491.605 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. In macrophages and melanoma cells, isoform 5 may participate in the control of podosome and invadopodia formation.
- Gene Name:
- SCN8A
- Uniprot ID:
- Q9UQD0
- Molecular Weight:
- 225278.005 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Key regulator of striated muscle performance by acting as the major Ca(2+) ATPase responsible for the reuptake of cytosolic Ca(2+) into the sarcoplasmic reticulum. Catalyzes the hydrolysis of ATP coupled with the translocation of calcium from the cytosol to the sarcoplasmic reticulum lumen. Contributes to calcium sequestration involved in muscular excitation/contraction.
- Gene Name:
- ATP2A1
- Uniprot ID:
- O14983
- Molecular Weight:
- 110251.36 Da
- Mechanism of Action:
- This pyrethroid inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Prostaglandin e receptor activity
- Specific Function:
- Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
- Gene Name:
- PTGER2
- Uniprot ID:
- P43116
- Molecular Weight:
- 39759.945 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Voltage-gated sodium channel activity involved in purkinje myocyte action potential
- Specific Function:
- Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-1 can modulate multiple alpha subunit isoforms from brain, skeletal muscle, and heart. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons.Isoform 2: Cell adhesion molecule that plays a critical role in neuronal migration and pathfinding during brain development. Stimulates neurite outgrowth.
- Gene Name:
- SCN1B
- Uniprot ID:
- Q07699
- Molecular Weight:
- 24706.955 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
- Specific Function:
- Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-2 causes an increase in the plasma membrane surface area and in its folding into microvilli. Interacts with TNR may play a crucial role in clustering and regulation of activity of sodium channels at nodes of Ranvier (By similarity).
- Gene Name:
- SCN2B
- Uniprot ID:
- O60939
- Molecular Weight:
- 24325.69 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
- Specific Function:
- Modulates channel gating kinetics. Causes unique persistent sodium currents. Inactivates the sodium channel opening more slowly than the subunit beta-1. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons (By similarity).
- Gene Name:
- SCN3B
- Uniprot ID:
- Q9NY72
- Molecular Weight:
- 24702.08 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
- Specific Function:
- Modulates channel gating kinetics. Causes negative shifts in the voltage dependence of activation of certain alpha sodium channels, but does not affect the voltage dependence of inactivation. Modulates the suceptibility of the sodium channel to inhibition by toxic peptides from spider, scorpion, wasp and sea anemone venom.
- Gene Name:
- SCN4B
- Uniprot ID:
- Q8IWT1
- Molecular Weight:
- 24968.755 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Signal transducer activity
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of the calcium.
- Gene Name:
- ATP2C1
- Uniprot ID:
- P98194
- Molecular Weight:
- 100576.42 Da
- Mechanism of Action:
- This pyrethroid inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Zinc ion binding
- Specific Function:
- May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments. Degrades fibronectin but not laminin or Pz-peptide.
- Gene Name:
- MMP9
- Uniprot ID:
- P14780
- Molecular Weight:
- 78457.51 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Transcriptionally controlled transcription factor. Binds to DNA sites required for the transcription of alpha 1-antitrypsin, apolipoprotein CIII, transthyretin genes and HNF1-alpha. May be essential for development of the liver, kidney and intestine.
- Gene Name:
- HNF4A
- Uniprot ID:
- P41235
- Molecular Weight:
- 52784.205 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Gene Name:
- SCN3A
- Uniprot ID:
- Q9NY46
- Molecular Weight:
- 226291.905 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity involved in sa node cell action potential
- Specific Function:
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential. Channel inactivation is regulated by intracellular calcium levels.
- Gene Name:
- SCN5A
- Uniprot ID:
- Q14524
- Molecular Weight:
- 226937.475 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-sensitive Na(+) channel isoform. Plays a role in pain mechanisms, especially in the development of inflammatory pain (By similarity).
- Gene Name:
- SCN9A
- Uniprot ID:
- Q15858
- Molecular Weight:
- 226370.175 Da
- Mechanism of Action:
- This pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT .
References
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
- General Function:
- Metal ion binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium. Transports calcium ions from the cytosol into the sarcoplasmic/endoplasmic reticulum lumen. Contributes to calcium sequestration involved in muscular excitation/contraction.
- Gene Name:
- ATP2A3
- Uniprot ID:
- Q93084
- Molecular Weight:
- 113976.23 Da
- Mechanism of Action:
- This pyrethroid inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]