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Wikipedia

Diphenadione

Diphenadione is a vitamin K antagonist that has anticoagulant effects and is used as a rodenticide against rats, mice, voles, ground squirrels and other rodents. The chemical compound is an anti-coagulant with active half-life longer than warfarin and other synthetic 1,3-indandione anticoagulants.[3][4]

Diphenadione
Names
Preferred IUPAC name
2-(Diphenylacetyl)-1H-indene-1,3(2H)-dione
Other names
Diphacinone; Diphenandione, Difenacin,[1] Ratindan[2][3]
Identifiers
  • 82-66-6 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1413199
ChemSpider
  • 6463
ECHA InfoCard 100.001.304
KEGG
  • D07136 Y
  • 6719
UNII
  • 54CA01C6JX Y
  • DTXSID4032378
  • InChI=1S/C23H16O3/c24-21-17-13-7-8-14-18(17)22(25)20(21)23(26)19(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14,19-20H
    Key: JYGLAHSAISAEAL-UHFFFAOYSA-N
  • InChI=1/C23H16O3/c24-21-17-13-7-8-14-18(17)22(25)20(21)23(26)19(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14,19-20H
    Key: JYGLAHSAISAEAL-UHFFFAOYAR
  • O=C2c1ccccc1C(=O)C2C(=O)C(c3ccccc3)c4ccccc4
Properties
C23H16O3
Molar mass 340.378 g·mol−1
Pharmacology
B01AA10 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

It is toxic to mammals, in all forms; exposure and oral ingestion of the toxin may cause irregular heartbeat and major maladies associated with its impact on blood clotting, depending on dose.[5] As a "second-generation" anticoagulant, diphenadione is more toxic than the first generation compounds (e.g., warfarin).[6]: 436  For purposes of treating toxicity on exposure, diphenadione is grouped with other vitamin K antagonists (coumarins and indandiones); despite being directed at rodents and being judged as less hazardous to humans and domestic animals than other rodenticides in use[when?] (by the U.S. Environmental Protection Agency), indandione anticoagulants, nevertheless, "may cause human toxicity at a much lower dose than conventional 'first-generation anticoagulants'… and can bioaccumulate in the liver."[7]: 173 

References edit

  1. ^ Kukovinets, O. S.; Abdullin, M. I.; Zainullin, R. A.; Kunakova, R. V. (2008). Chemical and Physical Methods for Protecting Biopolymers Against Pests. New York: Nova Biomedical Books. p. 185. ISBN 9781604563313.
  2. ^ "Catalog.md". Retrieved 3 April 2020.
  3. ^ a b EXTOXNET Staff (1993-09-01). "Diphacinone". EXTOXNET. Retrieved 2011-12-07.
  4. ^ Meister, R.T. (ed.). 1992. Farm Chemicals Handbook '92. Meister Publishing Company, Willoughby, OH.
  5. ^ Bell Laboratories, Inc. July, 1990. Diphacinone Technical: MSDS. Bell Labs, Madison, WI.
  6. ^ Murphy, Michael J.; Talcott, Patricia A. (2013). "Anticoagulant Rodenticides (Ch. 32)". In Peterson, Michael E.; Talcott, Patricia A. (eds.). Small Animal Toxicology (3rd ed.). St. Louis, MO, US: Elsevier Health Sciences. pp. 435–446, esp. 435–439. ISBN 978-0323241984. Retrieved 5 April 2016.
  7. ^ Reigart, J. Routt & Roberts, James R. (Eds.) (2013). "Rodenticides (Ch. 18, § Coumarins and Indandiones)" (PDF). Recognition and Management of Pesticide Poisonings (6th ed.). Corvallis, OR, US: National Pesticide Information Center (Oregon State University and the U.S. Environmental Protection Agency. Retrieved 5 April 2016. The first-generation anticoagulants, for example, are reasonably effective against pest rodents and are less toxic than second-generation anticoagulants… / Very small amounts of the extremely toxic rodenticides sodium fluoroacetate, fluoracetamide, strychnine, crimidine, yellow phosphorus, zinc phosphide and thallium sulfate can cause severe and even fatal poisoning. Cholecalciferol is also a highly toxic agent. The anticoagulants, indandiones and red squill, are less hazardous to humans and domestic animals. Some of the newer anticoagulant compounds, termed 'second-generation anticoagulants,' may cause human toxicity at a much lower dose than conventional 'first-generation anticoagulants'… and can bioaccumulate in the liver…{{cite book}}: CS1 maint: multiple names: authors list (link) [p. 173, emphasis in source].

Further reading edit

diphenadione, vitamin, antagonist, that, anticoagulant, effects, used, rodenticide, against, rats, mice, voles, ground, squirrels, other, rodents, chemical, compound, anti, coagulant, with, active, half, life, longer, than, warfarin, other, synthetic, indandio. Diphenadione is a vitamin K antagonist that has anticoagulant effects and is used as a rodenticide against rats mice voles ground squirrels and other rodents The chemical compound is an anti coagulant with active half life longer than warfarin and other synthetic 1 3 indandione anticoagulants 3 4 Diphenadione NamesPreferred IUPAC name 2 Diphenylacetyl 1H indene 1 3 2H dioneOther names Diphacinone Diphenandione Difenacin 1 Ratindan 2 3 IdentifiersCAS Number 82 66 6 Y3D model JSmol Interactive imageChEMBL ChEMBL1413199ChemSpider 6463ECHA InfoCard 100 001 304KEGG D07136 YPubChem CID 6719UNII 54CA01C6JX YCompTox Dashboard EPA DTXSID4032378InChI InChI 1S C23H16O3 c24 21 17 13 7 8 14 18 17 22 25 20 21 23 26 19 15 9 3 1 4 10 15 16 11 5 2 6 12 16 h1 14 19 20HKey JYGLAHSAISAEAL UHFFFAOYSA NInChI 1 C23H16O3 c24 21 17 13 7 8 14 18 17 22 25 20 21 23 26 19 15 9 3 1 4 10 15 16 11 5 2 6 12 16 h1 14 19 20HKey JYGLAHSAISAEAL UHFFFAOYARSMILES O C2c1ccccc1C O C2C O C c3ccccc3 c4ccccc4PropertiesChemical formula C 23H 16O 3Molar mass 340 378 g mol 1PharmacologyATC code B01AA10 WHO Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references It is toxic to mammals in all forms exposure and oral ingestion of the toxin may cause irregular heartbeat and major maladies associated with its impact on blood clotting depending on dose 5 As a second generation anticoagulant diphenadione is more toxic than the first generation compounds e g warfarin 6 436 For purposes of treating toxicity on exposure diphenadione is grouped with other vitamin K antagonists coumarins and indandiones despite being directed at rodents and being judged as less hazardous to humans and domestic animals than other rodenticides in use when by the U S Environmental Protection Agency indandione anticoagulants nevertheless may cause human toxicity at a much lower dose than conventional first generation anticoagulants and can bioaccumulate in the liver 7 173 References edit Kukovinets O S Abdullin M I Zainullin R A Kunakova R V 2008 Chemical and Physical Methods for Protecting Biopolymers Against Pests New York Nova Biomedical Books p 185 ISBN 9781604563313 Catalog md Retrieved 3 April 2020 a b EXTOXNET Staff 1993 09 01 Diphacinone EXTOXNET Retrieved 2011 12 07 Meister R T ed 1992 Farm Chemicals Handbook 92 Meister Publishing Company Willoughby OH Bell Laboratories Inc July 1990 Diphacinone Technical MSDS Bell Labs Madison WI Murphy Michael J Talcott Patricia A 2013 Anticoagulant Rodenticides Ch 32 In Peterson Michael E Talcott Patricia A eds Small Animal Toxicology 3rd ed St Louis MO US Elsevier Health Sciences pp 435 446 esp 435 439 ISBN 978 0323241984 Retrieved 5 April 2016 Reigart J Routt amp Roberts James R Eds 2013 Rodenticides Ch 18 Coumarins and Indandiones PDF Recognition and Management of Pesticide Poisonings 6th ed Corvallis OR US National Pesticide Information Center Oregon State University and the U S Environmental Protection Agency Retrieved 5 April 2016 The first generation anticoagulants for example are reasonably effective against pest rodents and are less toxic than second generation anticoagulants Very small amounts of the extremely toxic rodenticides sodium fluoroacetate fluoracetamide strychnine crimidine yellow phosphorus zinc phosphide and thallium sulfate can cause severe and even fatal poisoning Cholecalciferol is also a highly toxic agent The anticoagulants indandiones and red squill are less hazardous to humans and domestic animals Some of the newer anticoagulant compounds termed second generation anticoagulants may cause human toxicity at a much lower dose than conventional first generation anticoagulants and can bioaccumulate in the liver a href Template Cite book html title Template Cite book cite book a CS1 maint multiple names authors list link p 173 emphasis in source Further reading editReigart J Routt amp Roberts James R Eds 2013 Rodenticides Ch 18 Coumarins and Indandiones PDF Recognition and Management of Pesticide Poisonings 6th ed Corvallis OR US National Pesticide Information Center Oregon State University and the U S Environmental Protection Agency pp 173 187 Retrieved 5 April 2016 a href Template Cite book html title Template Cite book cite book a CS1 maint multiple names authors list link A safety handbook that explains how incidents of poisoning by various rodenticides are treated Retrieved from https en wikipedia org w index php title Diphenadione amp oldid 1047049173, wikipedia, wiki, book, books, library,

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