Diphenadione

Chemical compound From Wikipedia, the free encyclopedia

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.[4] The chemical compound is an anti-coagulant with active half-life longer than warfarin and other synthetic 1,3-indandione anticoagulants.[3][5]

Quick facts Names, Identifiers ...
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).
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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.[6] As a "second-generation" anticoagulant, diphenadione is more toxic than the first generation compounds (e.g., warfarin).[7]: 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."[8]: 173 

Rat poisons with diphacinone are often dyed bright blue to signal toxicity.[9]

References

Further reading

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