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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=CC=CC=C3OC2=O)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
Palatability and toxicity of fipronil as a systemic insecticide in a bromadiolone rodenticide bait for rat and flea control.
2001 Sep
A scheme for the placement of rodenticide baits for rat eradication on confinement livestock farms.
2003 May 15
Anticoagulant rodenticides.
2005
[One case of acute severe bromadiolone poisoning].
2005 Dec
Study on the fluorescence characteristics of bromadiolone in aqueous and organized media and application in analysis.
2005 Dec
Fluorescence spectroscopic study of serum albumin-bromadiolone interaction: fluorimetric determination of bromadiolone.
2005 Jul 1
[Analysis of bromadiolone in blood by liquid chromatography-mass spectrometry].
2005 Nov
[Bromadiolone poisoning in foxes].
2006 Aug
Effect of bromadiolone on haematology, liver and kidney in Mus musculus.
2006 Jan
Acute bromadiolone intoxication.
2006 May
Persistence of bromadiolone anticoagulant rodenticide in Arvicola terrestris populations after field control.
2006 Nov
Efficiency of three anti-coagulant rodenticides on commensal rodents.
2007 Aug
Multiresidue analysis of seven anticoagulant rodenticides by high-performance liquid chromatography/electrospray/mass spectrometry.
2007 Feb 7
Exposure of raptors and waterbirds to anticoagulant rodenticides (difenacoum, bromadiolone, coumatetralyl, coumafen, brodifacoum): epidemiological survey in Loire Atlantique (France).
2007 Jul
[Determination of five 4-hydroxycoumarin rodenticides in whole blood by high performance liquid chromatography with fluorescence detection].
2007 Mar
Kinetics of bromadiolone in rodent populations and implications for predators after field control of the water vole, Arvicola terrestris.
2008 Dec 15
Differential expression of cytochrome P450 genes between bromadiolone-resistant and anticoagulant-susceptible Norway rats: a possible role for pharmacokinetics in bromadiolone resistance.
2008 Mar
Pharmacokinetics of eight anticoagulant rodenticides in mice after single oral administration.
2008 Oct
Bromadiolone toxicokinetics: diagnosis and treatment implications.
2008 Sep
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
Novel mutations in the VKORC1 gene of wild rats and mice--a response to 50 years of selection pressure by warfarin?
2009 Feb 6
Consequences of the Y139F Vkorc1 mutation on resistance to AVKs: in-vivo investigation in a 7th generation of congenic Y139F strain of rats.
2009 Oct
Susceptibility of bromadiolone anticoagulant rodenticide in two rodent species and its haematologic effect.
2010 Apr
Anticoagulant rodenticides in three owl species from Western Canada, 1988-2003.
2010 Feb
Bromadiolone susceptibility in wild and laboratory Mus musculus L.(house mice) in Buenos Aires, Argentina.
2010 Feb
Accumulation of anticoagulant rodenticides in a non-target insectivore, the European hedgehog (Erinaceus europaeus).
2010 Jan
Analysis of multiple anticoagulant rodenticides in animal blood and liver tissue using principles of QuEChERS method.
2010 Jun
Warfarin toxicity and individual variability-clinical case.
2010 Nov
Determination of bromadiolone residues in fox faeces by LC/ESI-MS in relationship with toxicological data and clinical signs after repeated exposure.
2010 Oct
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 Sat Dec 16 10:51:19 UTC 2023
Edited
by admin
on Sat Dec 16 10:51:19 UTC 2023
Record UNII
J2FR050NM5
Record Status Validated (UNII)
Record Version
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Name Type Language
BROMADIOLONE
ISO   MI  
Common Name English
BROMADIOLONE [MI]
Common Name English
SUPER-CAID
Brand Name English
BROMONE
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 Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID201337347
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
249-205-9
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
CAS
28772-56-7
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
Bromadiolone
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
MERCK INDEX
m2659
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY Merck Index
EVMPD
SUB33433
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
HSDB
6458
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
FDA UNII
J2FR050NM5
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
CAS
198015-14-4
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
PUBCHEM
54680085
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY
SMS_ID
100000126256
Created by admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
PRIMARY