Brodifacoum (CHEM002435)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:17 UTC
Update Date2026-04-03 01:14:40 UTC
Accession NumberCHEM002435
Identification
Common NameBrodifacoum
ClassSmall Molecule
DescriptionBrodifacoum is a highly lethal anticoagulant poison derived from coumarin. It is typically used as a rodenticide but is also used to control larger mammalian pests. (1)
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Ester
  • Household Toxin
  • Organic Compound
  • Organobromide
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC31H23BrO3
Average Molecular Mass523.417 g/mol
Monoisotopic Mass522.083 g/mol
CAS Registry Number56073-10-0
IUPAC Name3-{3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl}-2-hydroxy-4H-chromen-4-one
Traditional Namebrodifacoum
SMILESOC1=C(C2CC(CC3=CC=CC=C23)C2=CC=C(C=C2)C2=CC=C(Br)C=C2)C(=O)C2=CC=CC=C2O1
InChI IdentifierInChI=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/h1-16,23,27,34H,17-18H2
InChI KeyLNDUTAIPEYOCDF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassPhenylnaphthalenes
Direct ParentPhenylnaphthalenes
Alternative Parents
Substituents
  • Phenylnaphthalene
  • Brominated biphenyl
  • Biphenyl
  • Chromone
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Tetralin
  • Bromobenzene
  • Pyranone
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organobromide
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point230°C
Boiling PointNot Available
Solubility3.8e-06 mg/mL at 20°C [TOMLIN,C (1997); pH 5.2]
Predicted Properties
PropertyValueSource
Water Solubility4.6e-05 g/LALOGPS
logP7.63ALOGPS
logP8.4ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)8.19ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity151.41 m³·mol⁻¹ChemAxon
Polarizability54.48 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0011090000-85319378506888ebe218Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0axr-0476290000-efaf2111f7eb8e658f10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i0-0962220000-6dce943e76b9c5f2bcd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-0000960000-cf53f8b648a6cddc4605Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0300940000-db8a0ec324f2389e0308Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-8529800000-634fce5b94ab2e593c2cSpectrum
Toxicity Profile
Route of ExposureOral (ingestion) (2) ; dermal (2)
Mechanism of ToxicityBrodifacoum inhibits the enzyme Vitamin K epoxide reductase. This enzyme is needed for the reconstitution of the vitamin K in its cycle from vitamin K-epoxide, and so brodifacoum steadily decreases the level of active vitamin K in the blood. Vitamin K is required for the synthesis of important substances including prothrombin, which is involved in blood clotting. This disruption becomes increasingly severe until the blood effectively loses any ability to clot. In addition, brodifacoum increases permeability of blood capillaries. The blood plasma and blood itself begins to leak from the blood vessels, causing internal bleeding leading to shock, loss of consciousness, and eventually death. (1)
MetabolismNot Available
Toxicity ValuesLD50: 0.4 mg/kg (Oral, Mouse) (3)
Lethal Dose15 mg for an adult human. (1)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBrodifacoum is a highly lethal anticoagulant poison used as a pesticide. It is typically used as a rodenticide but is also used to control larger mammalian pests. (1)
Minimum Risk LevelNot Available
Health EffectsBrodifacoum is an anticoagulant and causes internal bleeding, leading to shock, loss of consciousness, and eventually death. (1)
SymptomsBrodifacoum initially causes dehydration before progressing to bleeding complications. (1)
TreatmentThe primary antidote to brodifacoum poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses brodifacoum can affect the body for many months, and the antidote must be administered regularly for a long period of time. (1)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBrodifacoum
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID41736
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available