Diphenadione
Structural formula of diphenadione
Ball-and-stick model of the diphenadione molecule
Names
Preferred IUPAC name
2-(Diphenylacetyl)-1H-indene-1,3(2H)-dione
Other names
Diphacinone; Diphenandione, Difenacin,[1] Ratindan[2][3]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.304 Edit this at Wikidata
KEGG
UNII
  • 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).
checkY verify (what is checkY☒N ?)

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]

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

  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

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