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Chemical Compound Review

Confidor     nitramide

Synonyms: Provado, Admire, Gaucho, Merit, Imidacloprid, ...
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Disease relevance of nitramide

  • Electrostatic interactions of the nitroimine group and bridgehead nitrogen in imidacloprid with particular nAChR amino acid residues are likely to have key roles in determining the selective toxicity of imidacloprid [1].
  • The effects of the nitromethylene heterocycle imidacloprid on the nicotinic acetylcholine receptor of clonal rat pheochromocytoma (PC 12) cells were studied using the single-channel patch clamp technique [2].
  • Imidacloprid/moxidectin topical solution for the prevention of heartworm disease and the treatment and control of flea and intestinal nematodes of cats [3].
  • Flea control with 3.75 mg of imidacloprid/kg of body weight ranged from 94.4 to 96.9% for days 14 to 28 and decreased to 91.6% by 34 days after treatment [4].
  • Specific treatment for spider bites is provided by the polyvalent anti-arachnidic antiserum produced by Butantan Institute, São Paulo, Brazil by immunizing horses with mixtures of venoms from Tityus serrulatus and T. bahiensis scorpions, as well as Phoneutria nigriventer and L. gaucho spiders [5].

Psychiatry related information on nitramide

  • The hypothesis raised was whether imidacloprid could migrate into nectar and pollen, then modify flower attractiveness, homing behavior, and colony development [6].

High impact information on nitramide

  • Recent studies using binding assays, molecular biology and electrophysiology suggest that both alpha- and non-alpha-subunits of nAChRs contribute to interactions of these receptors with imidacloprid [1].
  • Neonicotinoids, such as imidacloprid, are nicotinic acetylcholine receptor (nAChR) agonists with potent insecticidal activity [7].
  • A strong correlation between the frequency of the Y151S point mutation and the level of resistance to imidacloprid has been demonstrated by allele-specific PCR [7].
  • To investigate the mechanism of neonicotinoid selectivity, we have examined the effects of mutations to basic amino acid residues in loop D of the nAChR acetylcholine (ACh) binding site on the interactions with imidacloprid [8].
  • Computational, homology models of the agonist binding domain of the wild-type and mutant alpha4beta2 and Dalpha2beta2 nAChRs with imidacloprid bound were generated based on the crystal structures of acetylcholine binding proteins of Lymnaea stagnalis and Aplysia californica [8].

Chemical compound and disease context of nitramide


Biological context of nitramide


Anatomical context of nitramide

  • Here, we have used whole-cell patch-clamp recording of cholinergic neurons cultured from the central nervous system of 3rd instar Drosophila larvae to examine the actions of acetylcholine (ACh) and nicotine, as well as the neonicotinoids imidacloprid, clothianidin and P-CH-clothianidin on native nAChRs of these neurons [19].
  • 2. XENOPUS: oocytes expressing wild-type alpha7 nicotinic receptors respond to imidacloprid with rapid inward currents [20].
  • Without the addition of an electron donor, rabbit liver cytosol reduces IMI only to IMI-NO at a slow rate [21].
  • The effects of the nitromethylene heterocycle, imidacloprid, on the nicotinic acetylcholine receptor-channel of clonal rat phaeochromocytoma (PC12) cells were studied using whole-cell and single-channel patch clamp methods [22].
  • In order to assess the risk to mammals of a chronic exposure to imidacloprid (IMI), we investigated its absorption with the human intestinal Caco-2 cell line [17].

Associations of nitramide with other chemical compounds


Gene context of nitramide

  • Neonicotinoids such as the insecticide imidacloprid (IMI) act as agonists at the insect nicotinic acetylcholine receptor (nAChR) [27].
  • This is the first demonstration that imidacloprid selectively acts on Mp alpha2 and Mp alpha3 subunits, but not Mp alpha1, in M. persicae [28].
  • Furthermore, we show that pre-existing Rst(2)DDT alleles in turn confer cross-resistance to imidacloprid [29].
  • HSP27 was found to be underexpressed at concentrations of imidacloprid or endosulfan (as Techn'ufan) lower than IC50 [30].
  • In contrast, no specific binding of imidacloprid was detected when D alpha3 was co-expressed with the mammalian neuronal beta4 subunit, or with the muscle-type (gamma or delta) subunits [31].

Analytical, diagnostic and therapeutic context of nitramide

  • The models indicate that the nitro group of imidacloprid interacts directly with the introduced basic residues at position 77, whereas those at position 79 either prevent or permit such interactions depending on their electrostatic properties, thereby explaining the observed functional changes resulting from site-directed mutagenesis [8].
  • We developed a method for the determination of low amounts of imidacloprid in soils, plants (leaves and flowers), and pollens by using HPLC coupled to tandem mass spectrometry (APCI-MS/MS) [32].
  • Determination of imidacloprid in vegetables by high-performance liquid chromatography with diode-array detection [33].
  • Under normal laboratory conditions, UV light had no significant influence on the outcome of toxicity bioassays, although in the case of imidacloprid both EC(50) and LC(50) calculated values were twice as high under the light as in the dark [13].
  • Development of an enzyme-linked immunosorbent assay for the insecticide imidacloprid [34].


  1. Neonicotinoids: insecticides acting on insect nicotinic acetylcholine receptors. Matsuda, K., Buckingham, S.D., Kleier, D., Rauh, J.J., Grauso, M., Sattelle, D.B. Trends Pharmacol. Sci. (2001) [Pubmed]
  2. Subconductance-state currents generated by imidacloprid at the nicotinic acetylcholine receptor in PC 12 cells. Nagata, K., Aistrup, G.L., Song, J.H., Narahashi, T. Neuroreport (1996) [Pubmed]
  3. Imidacloprid/moxidectin topical solution for the prevention of heartworm disease and the treatment and control of flea and intestinal nematodes of cats. Arther, R.G., Charles, S., Ciszewski, D.K., Davis, W.L., Settje, T.S. Vet. Parasitol. (2005) [Pubmed]
  4. Efficacy of imidacloprid for removal and control of fleas (Ctenocephalides felis) on dogs. Arther, R.G., Cunningham, J., Dorn, H., Everett, R., Herr, L.G., Hopkins, T. Am. J. Vet. Res. (1997) [Pubmed]
  5. Development and evaluation of the neutralizing capacity of horse antivenom against the Brazilian spider Loxosceles intermedia. Braz, A., Minozzo, J., Abreu, J.C., Gubert, I.C., Chávez-Olórtegui, C. Toxicon (1999) [Pubmed]
  6. Hazards of imidacloprid seed coating to Bombus terrestris (Hymenoptera: Apidae) when applied to sunflower. Tasei, J.N., Ripault, G., Rivault, E. J. Econ. Entomol. (2001) [Pubmed]
  7. A nicotinic acetylcholine receptor mutation conferring target-site resistance to imidacloprid in Nilaparvata lugens (brown planthopper). Liu, Z., Williamson, M.S., Lansdell, S.J., Denholm, I., Han, Z., Millar, N.S. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  8. Role in the selectivity of neonicotinoids of insect-specific basic residues in loop d of the nicotinic acetylcholine receptor agonist binding site. Shimomura, M., Yokota, M., Ihara, M., Akamatsu, M., Sattelle, D.B., Matsuda, K. Mol. Pharmacol. (2006) [Pubmed]
  9. Evaluation of the efficacy of a topically administered combination of imidacloprid and permethrin against Phlebotomus perniciosus in dog. Miró, G., Gálvez, R., Mateo, M., Montoya, A., Descalzo, M.A., Molina, R. Vet. Parasitol. (2007) [Pubmed]
  10. Field study on the insecticidal efficacy of Advantage against natural infestations of dogs with lice. Hanssen, I., Mencke, N., Asskildt, H., Ewald-Hamm, D., Dorn, H. Parasitol. Res. (1999) [Pubmed]
  11. Ecological effects of the insecticide imidacloprid and a pollutant from antidandruff shampoo in experimental rice fields. Sanchez-Bayo, F., Goka, K. Environ. Toxicol. Chem. (2006) [Pubmed]
  12. Acute poisoning with the neonicotinoid insecticide imidacloprid in N-methyl pyrrolidone. Wu, I.W., Lin, J.L., Cheng, E.T. J. Toxicol. Clin. Toxicol. (2001) [Pubmed]
  13. Influence of light in acute toxicity bioassays of imidacloprid and zinc pyrithione to zooplankton crustaceans. Sánchez-Bayo, F., Goka, K. Aquat. Toxicol. (2006) [Pubmed]
  14. Complex intracellular messenger pathways regulate one type of neuronal alpha-bungarotoxin-resistant nicotinic acetylcholine receptors expressed in insect neurosecretory cells (dorsal unpaired median neurons). Courjaret, R., Lapied, B. Mol. Pharmacol. (2001) [Pubmed]
  15. Effects of the alpha subunit on imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors. Matsuda, K., Buckingham, S.D., Freeman, J.C., Squire, M.D., Baylis, H.A., Sattelle, D.B. Br. J. Pharmacol. (1998) [Pubmed]
  16. Cloning, heterologous expression and co-assembly of Mpbeta1, a nicotinic acetylcholine receptor subunit from the aphid Myzus persicae. Huang, Y., Williamson, M.S., Devonshire, A.L., Windass, J.D., Lansdell, S.J., Millar, N.S. Neurosci. Lett. (2000) [Pubmed]
  17. Human intestinal absorption of imidacloprid with Caco-2 cells as enterocyte model. Brunet, J.L., Maresca, M., Fantini, J., Belzunces, L.P. Toxicol. Appl. Pharmacol. (2004) [Pubmed]
  18. Discrepancy between acute and chronic toxicity induced by imidacloprid and its metabolites in Apis mellifera. Suchail, S., Guez, D., Belzunces, L.P. Environ. Toxicol. Chem. (2001) [Pubmed]
  19. Neonicotinoid insecticides display partial and super agonist actions on native insect nicotinic acetylcholine receptors. Brown, L.A., Ihara, M., Buckingham, S.D., Matsuda, K., Sattelle, D.B. J. Neurochem. (2006) [Pubmed]
  20. Role of loop D of the alpha7 nicotinic acetylcholine receptor in its interaction with the insecticide imidacloprid and related neonicotinoids. Matsuda, K., Shimomura, M., Kondo, Y., Ihara, M., Hashigami, K., Yoshida, N., Raymond, V., Mongan, N.P., Freeman, J.C., Komai, K., Sattelle, D.B. Br. J. Pharmacol. (2000) [Pubmed]
  21. Identification of aldehyde oxidase as the neonicotinoid nitroreductase. Dick, R.A., Kanne, D.B., Casida, J.E. Chem. Res. Toxicol. (2005) [Pubmed]
  22. Modulation of the neuronal nicotinic acetylcholine receptor-channel by the nitromethylene heterocycle imidacloprid. Nagata, K., Song, J.H., Shono, T., Narahashi, T. J. Pharmacol. Exp. Ther. (1998) [Pubmed]
  23. Determination of imidacloprid and its metabolite 6-chloronicotinic acid in greenhouse air by application of micellar electrokinetic capillary chromatography with solid-phase extraction. Segura Carretero, A., Cruces-Blanco, C., Pérez Durán, S., Fernández Gutiérrez, A. Journal of chromatography. A. (2003) [Pubmed]
  24. Degradation of imidacloprid in water by photo-Fenton and TiO2 photocatalysis at a solar pilot plant: a comparative study. Malato, S., Caceres, J., Agüera, A., Mezcua, M., Hernando, D., Vial, J., Fernández-Alba, A.R. Environ. Sci. Technol. (2001) [Pubmed]
  25. Comparison of the activity of selamectin, fipronil, and imidacloprid against flea larvae (Ctenocephalides felis felis) in vitro. McTier, T.L., Evans, N.A., Martin-Short, M., Gration, K. Vet. Parasitol. (2003) [Pubmed]
  26. Efficacy and safety of imidacloprid10% plus moxidectin 2.5% spot-on in the treatment of sarcoptic mange and otoacariosis in dogs: results af a European field study. Krieger, K., Heine, J., Dumont, P., Hellmann, K. Parasitol. Res. (2005) [Pubmed]
  27. Novel neonicotinoid-agarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors. Tomizawa, M., Latli, B., Casida, J.E. J. Neurochem. (1996) [Pubmed]
  28. Molecular characterization and imidacloprid selectivity of nicotinic acetylcholine receptor subunits from the peach-potato aphid Myzus persicae. Huang, Y., Williamson, M.S., Devonshire, A.L., Windass, J.D., Lansdell, S.J., Millar, N.S. J. Neurochem. (1999) [Pubmed]
  29. DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid. Daborn, P., Boundy, S., Yen, J., Pittendrigh, B., ffrench-Constant, R. Mol. Genet. Genomics (2001) [Pubmed]
  30. Effect of selected insecticides on growth rate and stress protein expression in cultured human A549 and SH-SY5Y cells. Skandrani, D., Gaubin, Y., Beau, B., Murat, J.C., Vincent, C., Croute, F. Toxicology in vitro : an international journal published in association with BIBRA. (2006) [Pubmed]
  31. The influence of nicotinic receptor subunit composition upon agonist, alpha-bungarotoxin and insecticide (imidacloprid) binding affinity. Lansdell, S.J., Millar, N.S. Neuropharmacology (2000) [Pubmed]
  32. A LC/APCI-MS/MS method for analysis of imidacloprid in soils, in plants, and in pollens. Bonmatin, J.M., Moineau, I., Charvet, R., Fleche, C., Colin, M.E., Bengsch, E.R. Anal. Chem. (2003) [Pubmed]
  33. Determination of imidacloprid in vegetables by high-performance liquid chromatography with diode-array detection. Fernandez-Alba, A.R., Valverde, A., Agüera, A., Contreras, M., Chiron, S. Journal of chromatography. A. (1996) [Pubmed]
  34. Development of an enzyme-linked immunosorbent assay for the insecticide imidacloprid. Li, K., Li, Q.X. J. Agric. Food Chem. (2000) [Pubmed]
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