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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.304
KEGG
PubChem CID
UNII
InChI
  • 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
SMILES
  • O=C2c1ccccc1C(=O)C2C(=O)C(c3ccccc3)c4ccccc4
Properties
Chemical formula
 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).
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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 (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. 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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