Brodifacoum

Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide, but is also used to control larger pests such as possums.

Brodifacoum
Names
IUPAC name
3-[3-[4-(4-Bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-hydroxychromen-4-one
Other names
Bromfenacoum
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.054.509
PubChem CID
RTECS number
  • GN4934750
UNII
  • InChI=1S/C31H23BrO3/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2 Y
    Key: VEUZZDOCACZPRY-UHFFFAOYSA-N Y
  • InChI=1/C31H23BrO3/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2
    Key: VEUZZDOCACZPRY-UHFFFAOYAI
SMILES
  • Brc1ccc(cc1)c2ccc(cc2)C4Cc3ccccc3C(C4)C\5=C(/O)c6ccccc6OC/5=O
Properties
C31H23BrO3
Molar mass 523.426 g·mol−1
Melting point 228 to 230 °C (442 to 446 °F; 501 to 503 K)
Insoluble
Pharmacology
Routes of
administration
 Oral; dermal; inhalation (dusts) (for poisoning)
Pharmacokinetics:
100%
Metabolism
 slow, incomplete, hepatic
Slow; 20—130 days
faeces; very slow
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 270 μg/kg (rat, oral)
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 ?)
Infobox references

Brodifacoum has an especially long half-life in the body, which ranges up to nine months, requiring prolonged treatment with antidotal vitamin K for both human and pet poisonings. It has one of the highest risks of secondary poisoning to both mammals and birds. Significant experience in brodifacoum poisonings has been gained in many human cases where it has been used in attempted suicides, necessitating long periods of vitamin K treatment. In March 2018, cases of severe coagulopathy and bleeding associated with synthetic cannabinoid use contaminated with brodifacoum were reported in five states of the US.

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