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Details

Stereochemistry RACEMIC
Molecular Formula C30H23BrO4
Molecular Weight 527.405
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMADIOLONE

SMILES

O[C@H](C[C@@H](C1=CC=CC=C1)C2=C(O)C3=C(OC2=O)C=CC=C3)C4=CC=C(C=C4)C5=CC=C(Br)C=C5

InChI

InChIKey=OWNRRUFOJXFKCU-IZZNHLLZSA-N
InChI=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/h1-17,25-26,32-33H,18H2/t25-,26+/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H23BrO4
Molecular Weight 527.405
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Bromadiolone is a multi-feed, synthetic, second-generation anti-coagulant rodenticide. The active ingredient is formulated on a food base, typically cereal, to produce a ready to use bait containing 0.005% w/w bromadiolone. When compared to other anticoagulant rodenticides, bromadiolone has a good level of activity against the brown rat, and moderate levels of activity against mice. Bromadiolone is marginally more toxic to non-target 'farmyard' species than difenacoum. Bromadiolone is a potent poison to all mammal species and it is essential that all baits should be well protected from non-target animals. The best way to achieve this is by placing the baits in an approved bait box. Bromadiolone is a second-generation single-dose anticoagulant rodenticide. It disrupts the normal blood clotting mechanisms resulting in increased bleeding tendency and, eventually, profuse haemorrhage and death. Effectiveness of bromadiolone depends on exposure (i.e. consumption of the bait by the target organism).

CNS Activity

Curator's Comment: Due to its high lipid solubility, bromadiolone might easily diffuse across the blood−brain barrier and, therefore, cause CNS toxicity.

Originator

Curator's Comment: Bromadiolone {3-(3-(4'-bromobiphenyl-4-yl)-3-hydroxy-1-phenyl propyl)-4-hydroxycoumarin} was synthesized and marketed by the French company Lipha SA during the mid-1970s.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Korean patients with superwarfarin intoxication and their outcome.
2010-12
Warfarin toxicity and individual variability-clinical case.
2010-11
Prevalence of anticoagulant rodenticide poisoning in humans and animals in France and substances involved.
2010-11
An HPLC method for the determination of bromadiolone plasma kinetics and its residues in hen eggs.
2010-10
Determination of bromadiolone residues in fox faeces by LC/ESI-MS in relationship with toxicological data and clinical signs after repeated exposure.
2010-10
[Bromadiolone poisoning complicated with thrombosis in the lower extremities in a case].
2010-07
Residues in Brandt's voles (Microtus brandti) exposed to bromadiolone-impregnated baits in Mongolia.
2010-07
Analysis of multiple anticoagulant rodenticides in animal blood and liver tissue using principles of QuEChERS method.
2010-06
Susceptibility of bromadiolone anticoagulant rodenticide in two rodent species and its haematologic effect.
2010-04
Validation of a new liquid chromatography- tandem mass spectrometry ion-trap technique for the simultaneous determination of thirteen anticoagulant rodenticides, drugs, or natural products.
2010-03
Anticoagulant rodenticides in three owl species from Western Canada, 1988-2003.
2010-02
Bromadiolone susceptibility in wild and laboratory Mus musculus L.(house mice) in Buenos Aires, Argentina.
2010-02
Accumulation of anticoagulant rodenticides in a non-target insectivore, the European hedgehog (Erinaceus europaeus).
2010-01
Consequences of the Y139F Vkorc1 mutation on resistance to AVKs: in-vivo investigation in a 7th generation of congenic Y139F strain of rats.
2009-10
Novel mutations in the VKORC1 gene of wild rats and mice--a response to 50 years of selection pressure by warfarin?
2009-02-06
Evaluation of cholinesterase activities during in vivo intoxication using an electrochemical sensor strip - correlation with intoxication symptoms.
2009
Variation of cholinesterase-based biosensor sensitivity to inhibition by organophosphate due to ionizing radiation.
2009
Kinetics of bromadiolone in rodent populations and implications for predators after field control of the water vole, Arvicola terrestris.
2008-12-15
Pharmacokinetics of eight anticoagulant rodenticides in mice after single oral administration.
2008-10
Bromadiolone toxicokinetics: diagnosis and treatment implications.
2008-09
Bromadiolone poisoning: LC-MS method and pharmacokinetic data.
2008-07
Multi-residue analysis of eight anticoagulant rodenticides in animal plasma and liver using liquid chromatography combined with heated electrospray ionization tandem mass spectrometry.
2008-06-15
Second generation anticoagulant rodenticides in tawny owls (Strix aluco) from Great Britain.
2008-03-15
Differential expression of cytochrome P450 genes between bromadiolone-resistant and anticoagulant-susceptible Norway rats: a possible role for pharmacokinetics in bromadiolone resistance.
2008-03
Determination of bromadiolone in whole blood by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2007-08-24
Efficiency of three anti-coagulant rodenticides on commensal rodents.
2007-08
Exposure of raptors and waterbirds to anticoagulant rodenticides (difenacoum, bromadiolone, coumatetralyl, coumafen, brodifacoum): epidemiological survey in Loire Atlantique (France).
2007-07
How environment and vole behaviour may impact rodenticide bromadiolone persistence in wheat baits after field controls of Arvicola terrestris?
2007-07
[Determination of five 4-hydroxycoumarin rodenticides in whole blood by high performance liquid chromatography with fluorescence detection].
2007-03
Multiresidue analysis of seven anticoagulant rodenticides by high-performance liquid chromatography/electrospray/mass spectrometry.
2007-02-07
Characterization of bromadiolone resistance in a danish strain of Norway rats, Rattus norvegicus, by hepatic gene expression profiling of genes involved in vitamin K-dependent gamma-carboxylation.
2007
Persistence of bromadiolone anticoagulant rodenticide in Arvicola terrestris populations after field control.
2006-11
Reproductive success of bromadiolone-resistant rats in absence of anticoagulant pressure.
2006-09
[Bromadiolone poisoning in foxes].
2006-08
Acute bromadiolone intoxication.
2006-05
Assessment of ruminal degradation, oral bioavailability, and toxic effects of anticoagulant rodenticides in sheep.
2006-02
Effect of bromadiolone on haematology, liver and kidney in Mus musculus.
2006-01
Rapid determination of three anticoagulant rodenticides in whole blood by liquid chromatography coupled with electrospray ionization mass spectrometry.
2006
[One case of acute severe bromadiolone poisoning].
2005-12
Study on the fluorescence characteristics of bromadiolone in aqueous and organized media and application in analysis.
2005-12
[Analysis of bromadiolone in blood by liquid chromatography-mass spectrometry].
2005-11
The genetic basis of resistance to anticoagulants in rodents.
2005-08
Fluorescence spectroscopic study of serum albumin-bromadiolone interaction: fluorimetric determination of bromadiolone.
2005-07-01
Anticoagulant rodenticides.
2005
Evidence of secondary poisoning of free-ranging riparian mustelids by anticoagulant rodenticides in France: implications for conservation of European mink (Mustela lutreola).
2004-10
Vitamin K requirement in Danish anticoagulant-resistant Norway rats (Rattus norvegicus).
2003-08
Echinococcus multilocularis: secondary poisoning of fox population during a vole outbreak reduces environmental contamination in a high endemicity area.
2003-08
A scheme for the placement of rodenticide baits for rat eradication on confinement livestock farms.
2003-05-15
Spatial and temporal analysis of second-generation anticoagulant rodenticide residues in polecats (Mustela putorius) from throughout their range in Britain, 1992-1999.
2003
Palatability and toxicity of fipronil as a systemic insecticide in a bromadiolone rodenticide bait for rat and flea control.
2001-09
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: 5 vehicle control and 20 treated ICR mice per sex per group received intraperitoneal injections of bromadiolone technical (98.72% purity) at 0 (corn oil) and 400 mg/kg/day respectively for 3 days. http://www.cdpr.ca.gov/docs/risk/toxsums/pdfs/2135.pdf
In acute oral toxicity studies, bromadiolone was very toxic to rats with a LD50 to the rat of between 0.56 and 1.31 mg/kg bw. Bromadiolone is slightly less toxic to dogs with a LD50 value of 8.1 mg/kg bw. Repeated dose oral studies showed that at doses as low as 20 µg/kg/day in the dog, lethal effects developed after 64 to 85 days administration.
Route of Administration: Oral
Human whole blood lymphocytes were exposed in duplicate for 2 hours to bromadiolone technical (98.72% purity) in the presence of activation at 0, 37.5, 50.0, 74.9, and 99.9 ug/ml and for 26.1 hours in the absence of activation at concentrations of 0, 7.49, 9.99, 25.0, 50.0, and 74.9 ug/ml.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:28:35 GMT 2025
Edited
by admin
on Mon Mar 31 23:28:35 GMT 2025
Record UNII
J2FR050NM5
Record Status Validated (UNII)
Record Version
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Name Type Language
BROMADIOLONE
ISO   MI  
Common Name English
BROMONE
Preferred Name English
BROMADIOLONE [MI]
Common Name English
SUPER-CAID
Brand Name English
3-(3-(4'-BROMO-(1,1'-BIPHENYL)-4-YL)-3-HYDROXY-1-PHENYLPROPYL)-4-HYDROXYCOUMARIN
Systematic Name English
MAKI
Brand Name English
BROMADIOLONE [ISO]
Common Name English
LM-637
Code English
2H-1-BENZOPYRAN-2-ONE, 3-(3-(4'-BROMO(1,1'-BIPHENYL)-4-YL)-3-HYDROXY-1-PHENYLPROPYL)-4-HYDROXY-
Systematic Name English
Code System Code Type Description
ALANWOOD
bromadiolone
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID201337347
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
ECHA (EC/EINECS)
249-205-9
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
CAS
28772-56-7
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
Bromadiolone
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
MERCK INDEX
m2659
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY Merck Index
EVMPD
SUB33433
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
HSDB
6458
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
FDA UNII
J2FR050NM5
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
CAS
198015-14-4
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
PUBCHEM
54680085
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY
SMS_ID
100000126256
Created by admin on Mon Mar 31 23:28:35 GMT 2025 , Edited by admin on Mon Mar 31 23:28:35 GMT 2025
PRIMARY