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Showing toxin card for Diazinon (T3D0056)

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Version 1.0
Creation Date 2009-03-06 18:58:00
Update Date 2010-05-18 20:48:37
Accession Number T3D0056
Name Diazinon
Compound Type
  • Organic Compound
  • Organophosphate
  • Pesticide
Description Diazinon is the common name of O,O-diethyl-O-(2-isopropyl-6-methyl-pyrimidine-4-yl)phosphorothioate, a synthetic organophosphorus pesticide. It was formerly used as the active ingredient in household and garden products used to control pests such as flies, fleas, and cockroaches. Its use is now restricted to agricultural purposes and is used mainly on fruit and vegetable field crops. (R313, R314)
Synonyms
  1. Agridin 60
  2. Alfa-tox
  3. Antigal
  4. Antigal (van)
  5. Antlak
  6. Bassadinon
  7. Basudin
  8. Bazuden
  9. Bazudin
  10. Bazudine
  11. Ciazinon
  12. Dacutox
  13. Dassitox
  14. Dazzel
  15. Delzinon
  16. Di aterr-fos
  17. Diagran
  18. Dianon
  19. Diaterr-fos
  20. Diazajet
  21. Diazide
  22. Diazinon
  23. Diazinon AG 500
  24. Diazitol
  25. Diazol
  26. Dicid
  27. Diethyl 2-isopropyl-4-met hyl-6-pyrimidyl thionophosphate
  28. Diethyl 2-isopropyl-4-methyl-6-pyrimidyl thionophosphate
  29. Diethyl dimpylatum
  30. Dimpilato [inn-spanish]
  31. Dimpylat
  32. Dimpylate
  33. Dimpylate [inn]
  34. Dimpylatum
  35. Dimpylatum [inn-latin]
  36. Dipofene
  37. Disonex
  38. Dizictol
  39. Diziktol
  40. Dizinil
  41. Dizinon
  42. Drawizon
  43. Dyzol
  44. Ektoband
  45. Exodin
  46. Exodin (van)
  47. FL ytrol
  48. Fezudin
  49. Flytrol
  50. Galesan
  51. Gardentox
  52. Isopropylmethylpyrimidyl diethyl thiophosphate
  53. Kayazinon
  54. Kayazol
  55. Kleen-dok
  56. Meodinon
  57. Nedcidol
  58. Nemacur
  59. Neocidol
  60. Neocidol (oil)
  61. Neocidol veterinary powder
  62. Neodinon
  63. Neotsidol
  64. Nipsan
  65. Nucidol
  66. O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphate
  67. O,O-Diethyl-O-(2-isopropyl-4-methylpyrimidyl)thiophosphate
  68. Oleodiazinon
  69. Sarolex
  70. SpectrAcide
  71. Srolex
Chemical IUPAC Name ethyl [6-methyl-2-(propan-2-yl)pyrimidin-4-yl] ethoxy(sulfanylidene)phosphonite
Chemical Formula C12H21N2O3PS
Chemical Structure Structure
CAS Registry Number 333-41-5
InChI Identifier InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3
InChI Key InChIKey=FHIVAFMUCKRCQO-UHFFFAOYSA-N
PubChem Compound ID 3017 Link Image
KEGG ID C14324 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 34682 Link Image
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID D003976 Link Image
Stitch ID Diazinon Link Image
DrugBank ID Not Available
PDB ID Not Available
ACToR ID 411
Wikipedia Link Not Available
Monoisotopic Mass 304.10105
MOL File Show
PDB File Show
SDF File Show
SMILES CCOP(=S)(OCC)OC1=CC(C)=NC(=N1)C(C)C
Appearance Colorless oil (pure) or pale to dark brown liquid (technical).
Melting Point < 25 °C
Solubility 0.04 mg/mL at 25 °C [SHAROM,MS et al. (1980A)]
Predicted LogP 4.1921
Route of Exposure Oral (R313) ; inhalation (R313) ; dermal (R313)
Mechanism of Action Diazoxon the main toxic intermediate of diazinon, inhibits acetylcholinesterase in the central and peripheral nervous system. This results in the accumulation of acetylcholine, causing excessive stimulation of cholinergic fibers in the postganglionic parasympathetic nerve endings, neuromuscular junctions of the skeletal muscles, and cells of the central nervous system that results in hyperpolarization and receptor desensitization. This produces muscarinic, nicotinic, and CNS effects. Death is usually due to depression of the neurons in the brainstem, resulting in loss of respiratory drive and paralysis of the respiratory muscles, and/or cardiac failure. Diazinon cytotoxicity involves glutathione-modulated generation of reactive oxygen species, causing oxidative stress. (R313)
Metabolism Diazinon is absorbed via ingestion, inhalation, and dermal routes. It is rapidly metabolized and does not accumulate significantly in body tissues. Diazinon is metabolized by cytochrome P-450 enzymes, mainly CYP2C19, which initially oxidize it to the intermediate phosphooxythiran. Phosphooxythiran may undergo spontaneous desulfuration to form diazoxon, the main toxic intermediate. Alternatively, phosphooxythiran may be deactivated via hydrolysis, desulfuration, and deoxygenation to form metabolites 2-isopropyl4- methyl-6-hydroxypyrimidine (IMHP), diethylthiophosphate (DETP), and DEP, all of which are excreted in the urine. Detoxification of diazoxon to IMHP and DEP occurs via hydrolysis catalyzed by hepatic and extrahepatic A-esterases and B-esterases. (R313)
Toxicity Values LD50: 66 mg/kg (Oral, Rat) (R263) LD50: 180 mg/kg (Dermal, Rat) (R263) LD50: 65 mg/kg (Intraperitoneal, Rat) (R263) LD50: 58 mg/kg (Subcutaneous, Mouse) (R263) LD50: 180 mg/kg (Intravenous, Mouse) (R263)
Lethal Dose 25 g for an adult human. (R008)
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Diazinon is used as an insecticide in agriculture, mainly on fruit and vegetable field crops. (R313)
Minimum Risk Level Intermediate Inhalation: 0.01 mg/m3 (R260) Acute Oral: 0.006 mg/kg/day (R260) Intermediate Oral: 0.002 mg/kg/day (R260) Chronic Oral: 0.0007 mg/kg/day (R260)
Health Effects Diazinon affects mainly the nervous system. Exposure to high concentrations may results in coma and possibly death. (R313)
Symptoms The symptoms associated with diazinon poisoning in humans include weakness, headaches, tightness in the chest, blurred vision, nonreactive pinpoint pupils, excessive salivation, difficulty breathing, sweating, nausea, vomiting, diarrhea, abdominal cramps, and slurred speech. (R314)
Treatment Diazinon poisoning may be treated with the antidote atropine and/or certain oximes. Artificial respiration may be needed. (R315)
General References
  • R263 - Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  • R314 - Wikipedia. Diazinon. Last Updated 21 February 2009.
  • R008 - Ellenhorn MJ and Barceloux DG (1988). Diagnosis and treatment of human poisoning. Medical Toxicology. New York, New York: Elsevier Science Publishing Company, Inc.
  • R313 - ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for diazinon. U.S. Public Health Service in collaboration with U.S.
  • R260 - ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA).
  • R315 - International Programme on Chemical Safety (IPCS) INCHEM (1998). Environmental Health Criteria for Diazinon.
Targets
  1. Acetylcholinesterase
  2. Probable arylformamidase
Target 1 [top]
Target 1 ID 312
Target 1 Name Acetylcholinesterase
Target 1 Mechanism of Action Diazoxon the main toxic intermediate of diazinon, inhibits acetylcholinesterase in the central and peripheral nervous system. This results in the accumulation of acetylcholine, causing excessive stimulation of cholinergic fibers in the postganglionic parasympathetic nerve endings, neuromuscular junctions of the skeletal muscles, and cells of the central nervous system that results in hyperpolarization and receptor desensitization. This produces muscarinic, nicotinic, and CNS effects. (R313)
Target 1 Description Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis
Target 1 Synonyms
  1. AChE
Target 1 Gene Name ACHE
Target 1 Protein Sequence >Acetylcholinesterase 
MRPPQCLLHTPSLASPLLLLLLWLLGGGVGAEGREDAELLVTVRGGRLRGIRLKTPGGPV
SAFLGIPFAEPPMGPRRFLPPEPKQPWSGVVDATTFQSVCYQYVDTLYPGFEGTEMWNPN
RELSEDCLYLNVWTPYPRPTSPTPVLVWIYGGGFYSGASSLDVYDGRFLVQAERTVLVSM
NYRVGAFGFLALPGSREAPGNVGLLDQRLALQWVQENVAAFGGDPTSVTLFGESAGAASV
GMHLLSPPSRGLFHRAVLQSGAPNGPWATVGMGEARRRATQLAHLVGCPPGGTGGNDTEL
VACLRTRPAQVLVNHEWHVLPQESVFRFSFVPVVDGDFLSDTPEALINAGDFHGLQVLVG
VVKDEGSYFLVYGAPGFSKDNESLISRAEFLAGVRVGVPQVSDLAAEAVVLHYTDWLHPE
DPARLREALSDVVGDHNVVCPVAQLAGRLAAQGARVYAYVFEHRASTLSWPLWMGVPHGY
EIEFIFGIPLDPSRNYTAEEKIFAQRLMRYWANFARTGDPNEPRDPKAPQWPPYTAGAQQ
YVSLDLRPLEVRRGLRAQACAFWNRFLPKLLSATDTLDEAERQWKAEFHRWSSYMVHWKN
QFDHYSKQDRCSDL
Target 1 Number of Residues 614
Target 1 Molecular Weight 67795.5
Target 1 Theoretical pI 6.24
Target 1 GO Classification
Function
catalytic activity
hydrolase activity
hydrolase activity, acting on ester bonds
carboxylic ester hydrolase activity
cholinesterase activity
Process
Not Available
Component
Not Available
Target 1 General Function Lipid transport and metabolism
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • 1-31
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non Essential
Target 1 Domain Function PF08674:AChE_tetra PF00135:COesterase
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P22303 Link Image
Target 1 Cellular Location Isoform H:Cell membrane
Target 1 Gene Sequence >1845 bp 
ATGAGGCCCCCGCAGTGTCTGCTGCACACGCCTTCCCTGGCTTCCCCACTCCTTCTCCTC
CTCCTCTGGCTCCTGGGTGGAGGAGTGGGGGCTGAGGGCCGGGAGGATGCAGAGCTGCTG
GTGACGGTGCGTGGGGGCCGGCTGCGGGGCATTCGCCTGAAGACCCCCGGGGGCCCTGTC
TCTGCTTTCCTGGGCATCCCCTTTGCGGAGCCACCCATGGGACCCCGTCGCTTTCTGCCA
CCGGAGCCCAAGCAGCCTTGGTCAGGGGTGGTAGACGCTACAACCTTCCAGAGTGTCTGC
TACCAATATGTGGACACCCTATACCCAGGTTTTGAGGGCACCGAGATGTGGAACCCCAAC
CGTGAGCTGAGCGAGGACTGCCTGTACCTCAACGTGTGGACACCATACCCCCGGCCTACA
TCCCCCACCCCTGTCCTCGTCTGGATCTATGGGGGTGGCTTCTACAGTGGGGCCTCCTCC
TTGGACGTGTACGATGGCCGCTTCTTGGTACAGGCCGAGAGGACTGTGCTGGTGTCCATG
AACTACCGGGTGGGAGCCTTTGGCTTCCTGGCCCTGCCGGGGAGCCGAGAGGCCCCGGGC
AATGTGGGTCTCCTGGATCAGAGGCTGGCCCTGCAGTGGGTGCAGGAGAACGTGGCAGCC
TTCGGGGGTGACCCGACATCAGTGACGCTGTTTGGGGAGAGCGCGGGAGCCGCCTCGGTG
GGCATGCACCTGCTGTCCCCGCCCAGCCGGGGCCTGTTCCACAGGGCCGTGCTGCAGAGC
GGTGCCCCCAATGGACCCTGGGCCACGGTGGGCATGGGAGAGGCCCGTCGCAGGGCCACG
CAGCTGGCCCACCTTGTGGGCTGTCCTCCAGGCGGCACTGGTGGGAATGACACAGAGCTG
GTAGCCTGCCTTCGGACACGACCAGCGCAGGTCCTGGTGAACCACGAATGGCACGTGCTG
CCTCAAGAAAGCGTCTTCCGGTTCTCCTTCGTGCCTGTGGTAGATGGAGACTTCCTCAGT
GACACCCCAGAGGCCCTCATCAACGCGGGAGACTTCCACGGCCTGCAGGTGCTGGTGGGT
GTGGTGAAGGATGAGGGCTCGTATTTTCTGGTTTACGGGGCCCCAGGCTTCAGCAAAGAC
AACGAGTCTCTCATCAGCCGGGCCGAGTTCCTGGCCGGGGTGCGGGTCGGGGTTCCCCAG
GTAAGTGACCTGGCAGCCGAGGCTGTGGTCCTGCATTACACAGACTGGCTGCATCCCGAG
GACCCGGCACGCCTGAGGGAGGCCCTGAGCGATGTGGTGGGCGACCACAATGTCGTGTGC
CCCGTGGCCCAGCTGGCTGGGCGACTGGCTGCCCAGGGTGCCCGGGTCTACGCCTACGTC
TTTGAACACCGTGCTTCCACGCTCTCCTGGCCCCTGTGGATGGGGGTGCCCCACGGCTAC
GAGATCGAGTTCATCTTTGGGATCCCCCTGGACCCCTCTCGAAACTACACGGCAGAGGAG
AAAATCTTCGCCCAGCGACTGATGCGATACTGGGCCAACTTTGCCCGCACAGGGGATCCC
AATGAGCCCCGAGACCCCAAGGCCCCACAATGGCCCCCGTACACGGCGGGGGCTCAGCAG
TACGTTAGTCTGGACCTGCGGCCGCTGGAGGTGCGGCGGGGGCTGCGCGCCCAGGCCTGC
GCCTTCTGGAACCGCTTCCTCCCCAAATTGCTCAGCGCCACCGACACGCTCGACGAGGCG
GAGCGCCAGTGGAAGGCCGAGTTCCACCGCTGGAGCTCCTACATGGTGCACTGGAAGAAC
CAGTTCGACCACTACAGCAAGCAGGATCGCTGCTCAGACCTGTGA
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID ACHE Link Image
Target 1 GenAtlas ID ACHE Link Image
Target 1 HGNC ID HGNC:108 Link Image
Target 1 Chromosome Location Not Available
Target 1 Locus 7q22
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • R313 - ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for diazinon. U.S. Public Health Service in collaboration with U.S.
Target 1 General References 2263619; 8299725; 14702039; 12853948; 15489334; 11239002
Target 2 [top]
Target 2 ID 545
Target 2 Name Probable arylformamidase
Target 2 Mechanism of Action Diazoxon inhibits liver kynurenine formamidase. (R317)
Target 2 Description Catalyzes the hydrolysis of N-formyl-L-kynurenine to L- kynurenine, the second step in the conversion of tryptophan to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity)
Target 2 Synonyms
  1. Kynurenine formamidase; KF
Target 2 Gene Name AFMID
Target 2 Protein Sequence >Probable arylformamidase 
MMDVSGVGFPSKVPWKKMSAEELENQYCPSRWVVRLGAEEALRTYSQIGIEATTRARATR
KSLLHVPYGDGEGEKVDIYFPDESSEALPFFLFFHGGYWQSGSKDESAFMVHPLTAQGVA
VVIVAYGIAPKGTLDHMVDQVTRSVAFVQKRYPSNKGIYLCGHSAGAHLAAMMLLADWTK
HGVTPNLRGFFLVSGVFDLEPIVYTSQNVALQLTLEDAQRNSPQLKVAQAQPVDPTCRVL
VVVGQFDSPEFHRQSWEFYQTLCQGEWKASFEELHDVDHFEIVENLTQKDNVLTQIILKT
IFQ
Target 2 Number of Residues 303
Target 2 Molecular Weight 33991.5
Target 2 Theoretical pI 5.78
Target 2 GO Classification
Function
Not Available
Process
Not Available
Component
Not Available
Target 2 General Function Lipid transport and metabolism
Target 2 Pathways Amino-acid degradation; L-tryptophan degradation via kynurenine pathway; L-kynurenine from L-tryptophan:step 2/2
Target 2 Reactions Not Available
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Non Essential
Target 2 Domain Function Not Available
Target 2 GenBank ID Protein Not Available
Target 2 UniProtKB ID Q63HM1 Link Image
Target 2 Cellular Location Cytoplasm, cytosol (By similarity). Nucleus (By similarity)
Target 2 Gene Sequence >927 bp 
ATGATGGATGTGTCTGGTGTGGGTTTCCCAAGCAAGGTTCCTTGGAAGAAGATGTCTGCA
GAGGAGCTGGAGAATCAGTACTGTCCCAGCCGATGGGTTGTCCGACTGGGAGCAGAGGAA
GCCTTGAGGACCTACTCACAGATAGGAATTGAAGCCACCACAAGGGCCCGGGCCACCAGG
AAGAGCCTGCTGCATGTCCCCTATGGAGACGGCGAAGGGGAGAAAGTGGACATTTACTTC
CCCGACGAGTCGTCTGAAGCCTTGCCTTTCTTCCTGTTCTTTCACGGAGGATACTGGCAG
AGCGGAAGTAAGGATGAGTCTGCCTTCATGGTCCACCCGCTGACGGCACAGGGAGTGGCC
GTGGTAATAGTGGCTTACGGCATCGCCCCCAAAGGCACCCTGGACCACATGGTAGACCAG
GTGACCCGCAGCGTTGCGTTTGTCCAGAAGCGGTATCCAAGCAACAAGGGAATTTACCTG
TGTGGACACTCAGCCGGGGCCCACCTGGCTGCCATGATGCTCCTGGCCGACTGGACCAAG
CATGGGGTCACGCCCAACCTCAGAGGCTTTTTCCTGGTGAGTGGGGTCTTTGACCTGGAG
CCCATCGTGTATACTTCACAGAACGTTGCTCTCCAGCTGACCCTGGAGGACGCTCAGAGG
AATAACCCCCAGCTGAAGGTGGCCCAGGCACAGCCGGTGGACCCCACCTGCCGTGTGCTG
GTGGTCGTGGGCCAGTTCGACTCCCCCGAATTCCACCGACAGTCCTGGGAGTTTTACCAG
GTACTCCCAGTGCAGACCCTGTGTCAAGGAGAGTGGAAAGCCTCATTTGAAGAGCTCCAC
GATGTGGACCACTTTGAAATTGTTGAGAATCTGACCCAGAAGGACAACGTGCTCACCCAG
ATTATCTTGAAAACAATCTTCCAGTAG
Target 2 GenBank Gene ID Not Available
Target 2 GeneCard ID AFMID Link Image
Target 2 GenAtlas ID AFMID Link Image
Target 2 HGNC ID HGNC:20910 Link Image
Target 2 Chromosome Location Chromosome:17
Target 2 Locus 17q25.3
Target 2 SNPs SNPJam Report Link Image
Target 2 Toxin References
  • R317 - Seifert J, Pewnim T: Alteration of mice L-tryptophan metabolism by the organophosphorous acid triester diazinon. Biochem Pharmacol. 1992 Dec 1;44(11):2243-50. [PubMed Link Image]
Target 2 General References 17974005; 15489334

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