Bromadiolone (T3D3102)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-23 18:26:17 UTC
Update Date2014-12-24 20:25:59 UTC
Accession NumberT3D3102
Identification
Common NameBromadiolone
ClassSmall Molecule
DescriptionBromadiolone is a potent anticoagulant and rodenticide. It is a second-generation coumarin derivative, often called a "super-warfarin" for its added potency and tendency to accumulate in the liver of the poisoned organism. (3)
Compound Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Ester
  • Organic Compound
  • Organobromide
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Boldo
Boot hill
Bromadiolon
Bromatrol
Bromodialone
Bromodiolone
Bromone
Bromore
Broprodifacoum
Canadien 2000
Contrac
Contrax
Eradic
MAKI
Rafix
Ratimus
Rotox
Sup'operats
Super-caid
Super-cald
Super-rozol
Temus
Topidion
Chemical FormulaC30H23BrO4
Average Molecular Mass527.405 g/mol
Monoisotopic Mass526.078 g/mol
CAS Registry Number28772-56-7
IUPAC Name3-{3-[4-(4-bromophenyl)phenyl]-3-hydroxy-1-phenylpropyl}-2-hydroxy-4H-chromen-4-one
Traditional Namebromadiolone
SMILESOC(CC(C1=CC=CC=C1)C1=C(O)OC2=CC=CC=C2C1=O)C1=CC=C(C=C1)C1=CC=C(Br)C=C1
InChI IdentifierInChI=1S/C30H23BrO4/c31-23-16-14-20(15-17-23)19-10-12-22(13-11-19)26(32)18-25(21-6-2-1-3-7-21)28-29(33)24-8-4-5-9-27(24)35-30(28)34/h1-17,25-26,32,34H,18H2
InChI KeyInChIKey=IUZFQERQUZLNKQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Homoisoflavone
  • Linear 1,3-diarylpropanoid
  • Brominated biphenyl
  • Biphenyl
  • Chromone
  • Coumarin
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Bromobenzene
  • Halobenzene
  • Aryl bromide
  • Benzenoid
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organohalogen compound
  • Organobromide
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxygen 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 Point205°C
Boiling PointNot Available
Solubility0.019 mg/mL at 20°C [TOMLIN,C (1997)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00037 g/LALOGPS
logP5.85ALOGPS
logP7.27ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)8.11ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity149.74 m³·mol⁻¹ChemAxon
Polarizability52.66 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0011090000-fa4ac84af89c0835fbd52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-0092250000-51693136ff8e8fa0dc2f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ir0-0391100000-9416a9a0d039c5a29b842016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0010970000-0f6977de39ba6a7975d62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03gi-0340950000-e863bcdfd1f358552f312016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3290500000-1aecac71621da29b0b062016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (4) ; dermal (4)
Mechanism of ToxicityBromadiolone 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 bromadiolone 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, bromadiolone 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. (2)
MetabolismNot Available
Toxicity ValuesLD50: 1.75 mg/kg (Oral, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBromadiolone is a potent rodenticide. (3)
Minimum Risk LevelNot Available
Health EffectsBromadiolone is an anticoagulant and causes internal bleeding, leading to shock, loss of consciousness, and eventually death. (2)
SymptomsBromadiolone initially causes dehydration before progressing to bleeding complications. (2)
TreatmentThe primary antidote to bromadiolone 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 bromadiolone can affect the body for many months, and the antidote must be administered regularly for a long period of time. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID34322
ChEMBL IDNot Available
ChemSpider ID31618
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDBromadiolone
PDB IDNot Available
ACToR ID13321
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3102.pdf
General References
  1. O'Neil MJ (ed) (2001). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc.
  2. Wikipedia. Brodifacoum. Last Updated 22 June 2009. [Link]
  3. Wikipedia. Bromadiolone. Last Updated 1 July 2009. [Link]
  4. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Vitamin K epoxide reductase complex subunit 1
General Function:
Vitamin-k-epoxide reductase (warfarin-sensitive) activity
Specific Function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K. Vitamin K is required for the gamma-carboxylation of various proteins, including clotting factors, and is required for normal blood coagulation, but also for normal bone development.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular Weight:
18234.3 Da
References
  1. Wikipedia. Brodifacoum. Last Updated 22 June 2009. [Link]