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Encyclopedia > Brodifacoum

Brodifacoum chemical structure
Brodifacoum Image File history File links Brodifacoum. ...

IUPAC name:

3-(3-(4'-bromobiphenyl-4-yl)-1,2,3,4- tetrahydro-1-naphthyl)-4-hydroxycoumarin IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...

CAS number
56073-10-0
RTECS number
GN4934750
Chemical formula C31H23BrO3
Molecular weight 523.4
Bioavailability 100%
Metabolism slow, incomplete, hepatal
Elimination half-life Slow; half-life 20 — 130 days
Excretion faeces; very slow
Pregnancy category X - Deadly poison
Legal status No therapeutic application. May be restricted as a deadly poison.
Routes of administration Oral; dermal; inhalation (dusts) (for poisoning)

Brodifacoum is a highly lethal 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 rabbits, possums and other mammalian pests[1]. CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... An anticoagulant is a substance that prevents coagulation; that is, it stops blood from clotting. ... The skull and crossbones symbol traditionally used to label a poisonous substance. ... the plane is spreading pesticide. ... Rat poisons are a category of pest control chemicals intended to kill rats. ... This article or section does not cite its references or sources. ... Superfamilies and Families Phalangeroidea Burramyidae Phalangeridae Petauroidea Pseudocheiridae Petauridae Tarsipedidae Acrobatidae A possum is any of about 63 small to medium-sized arboreal marsupial species native to Australia, New Guinea and Sulawesi. ...


Brodifacoum, like most anticoagulant poisons, has the advantage that one of its first effects is dehydration, forcing the unfortunate victim to move away from human habitation in search of water. As such, there is less chance that homeowners will be forced to deal with decomposing remains inside their building. Dehydrated bodies also dry out more readily, possibly leaving an odorless, mummified carcass. A mummy is a corpse whose skin and dried flesh have been preserved by either intentional or accidental exposure to chemicals, extreme cold or dryness, or airlessness. ...

Contents

Toxicology

Brodifacoum has a similar mode of action to warfarin. However due to very high potency and long duration of action (elimination half-life of 20 – 130 days), it is characterised as a "second generation" or "superwarfarin" anticoagulant.[2] Warfarin (also known under the brand names of Coumadin®, Jantoven®, Marevan®, and Waran®) is an anticoagulant medication that is administered orally or, very rarely, by injection. ... Half-Life For a quantity subject to exponential decay, the half-life is the time required for the quantity to fall to half of its initial value. ...


Brodifacoum 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. Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Vitamin K denotes a group of 2-methilo-naphthoquinone derivatives. ... Thrombin (activated Factor II) is a coagulation protein that has many effects in the coagulation cascade. ... Coagulation is the thickening or congealing of any liquid into solid clots. ...


In addition, brodifacoum (as with other anticoagulants in toxic doses) increases permeability of blood capillaries; the blood plasma and blood itself begins to leak from the smallest blood vessels. A poisoned animal will suffer progressively worsening internal bleeding, leading to shock, loss of consciousness, and eventually death. Permeability has several meanings: In electromagnetism, permeability is the degree of magnetisation of a material in response to a magnetic field. ... Shock is a serious medical condition where the tissue perfusion is insufficient to meet the required supply of oxygen and nutrients. ... For other uses, see Death (disambiguation). ...


Brodifacoum is highly lethal to mammals and birds, and extremely lethal to fish. It is a highly cumulative poison, due to its high lipophilicity and extremely slow elimination. To bioaccumulate literally means to accumulate in a biological system. ... ... Elimination is a residence hall game where every player is both the hunter and the hunted. ...


Following are acute LD50 values for various animals (mammals)[3]: An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ...

  • rats (oral) 0.27—0.30 mg/kg b.w.
  • mice (oral) 0.40 mg/kg b.w.
  • rabbits (oral) 0.30 mg/kg b.w.
  • guinea-pigs (oral) 0.28 mg/kg b.w.
  • cats (oral) 0.25 mg/kg b.w.
  • dogs (oral) 0.25 mg/kg b.w.

LD50 values for various birds varies from about 1 mg/kg b.w. — 20 mg/kg b.w.[4].


LC50 (concentration prone of killing 50% of animals exposed to it) for fish:

  • trout (96 hours exposure) 0.04 ppm[5]

Given these extremely high toxicities in various mammals, brodifacoum is classified as "extremely toxic" (LD50 < 1.0 mg/kg b.w.) and "very toxic" (T+; LD50 < 25 mg/kg b.w.), respectively. Because of its persistency, cumulative potential and high toxicities for various wildlife species, it is also considered an environmental pollutant (N; noxious to the environment). The readiness of brodifacoum to penetrate intact skin should be noted, and brodifacoum and commercial preparations containing it should be handled with respective care and precaution because of its skin resorptivity.


The estimated average fatal dose for an adult man (60 kg b.w.) is about 15 mg, without treatment[6]. However, due to low bait concentrations (usually 10 — 50 mg/kg bait, i.e. 0.001 — 0.005%) and slow onset of symptoms, and the existence of a highly effective antidote (appropriately dosed vitamin K1), brodifacoum is considered to be of relatively low hazard to humans.


Brand names

Brodifacoum is marketed under a large variety of trade names, including d-Con, Finale, Fologorat, Havoc, Jaguar, Klerat, Matikus, Mouser, Pestoff, Ratak+, Rodend, Talon, Volak and Volid.


Treatment

The primary antidote to brodifacoum poisoning is immediate administration of vitamin K1 (initialy 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. As high doses of brodifacoum can affect the body for many months, the antidote must be administered regularly for a long period with frequent monitoring of the prothrombin time. Vitamin K denotes a group of 2-methilo-naphthoquinone derivatives. ... The prothrombin time (PT) and its derived measures of prothrombin ratio (PR) and international normalized ratio (INR) are measures of the extrinsic pathway of coagulation. ...


If unabsorbed poison is still in the digestive system, gastric lavage followed by administration of activated charcoal may be required. Gastric lavage, also commonly called a stomach pump, is the process of cleaning out the contents of the stomach. ... Activated carbon (also called activated charcoal) is the more general term which includes material mostly derived from charcoal. ...


Further treatments to be considered include infusion of blood or plasma to counteract hypovolemic shock; and in severe cases, infusion of blood clotting factor concentrate. Human blood smear: a - erythrocytes; b - neutrophil; c - eosinophil; d - lymphocyte. ... Blood plasma is the liquid component of blood, in which the blood cells are suspended. ... In physiology and medicine, hypovolemia is a state of decreased blood volume; more specifically, decrease in volume of blood plasma. ...


Administration of vitamin C is also recommended (100 mg three times daily)[7]. 3D representation of vitamin C Chemical structure of vitamin C Vitamin C is a water-soluble nutrient and human vitamin essential for life and for maintaining optimal health, used by the body for many purposes. ...


Another potential treatment is phenobarbital, which is believed to accelerate the metabolism of some anticoagulants via enzyme induction. Phenobarbital (also phenobarbitone) (Luminal®) is a weak acid with the chemical formula C12H12N2O3. ... Enzyme induction is a process in which a molecule ( a drug) induces ( initiates or enhances) the expression of an enzyme. ...


Poisoning case reports

There have been at least ten case reports of brodifacoum intoxication in the medical literature.


In one report[8], a woman deliberately consumed over 1.5 kilograms of rat bait, constituting about 75 mg brodifacoum, but made a full recovery after receiving conventional medical treatment.


In another report[9], a 17-year-old boy presented to the hospital with a severe bleeding disorder. It was discovered that he habitually smoked a mixture of brodifacoum and marijuana. Despite treatment with vitamin K, the bleeding disorder persisted for several months. He eventually recovered. A Cannabis sativa plant The drug cannabis, also called marijuana, is produced from parts of the cannabis plant, primarily the cured flowers and gathered trichomes of the female plant. ...


Notes

  1. ^ Eason, C.T. and Wickstrom, M. Vertebrate pesticide toxicology manual, New Zealand Department of Conservation
  2. ^ http://www.inchem.org/documents/hsg/hsg/hsg093.htm
  3. ^ http://www.inchem.org/documents/pds/pds/pest57_e.htm
  4. ^ http://www.inchem.org/documents/hsg/hsg/hsg093.htm
  5. ^ http://www.wil-kil.com/public/2005-06_labels-msds/WeatherBlok%20XT%20M.pdf#search=%22LC50%2Bbrodifacoum%22
  6. ^ http://www.inchem.org/documents/hsg/hsg/hsg093.htm
  7. ^ http://www.inchem.org/documents/pds/pds/pest57_e.htm
  8. ^ Lipton, R.A. & Klass, E.M. (1984) Human ingestion of a 'superwarfarin' rodenticide resulting in a prolonged anticoagulant effect. JAMA 252:3004-3005.
  9. ^ La Rosa, F, Clarke, S. & Lefkowitz, J. B. (1997) Brodifacoum intoxication with marijuana smoking. Archives of Pathology & Laboratory Medicine 121:67-69.

The Department of Conservation (In Māori, Te Papa Atawhai), commonly known by its acronym, DOC, is the state sector organisation of New Zealand which deals with the conservation of New Zealand’s natural and historic heritage. ... JAMA is the acronym for the Journal of the American Medical Association, a leading medical journal. ...

Further reading

  • Tasheva, M. (1995). Environmental Health Criteria 175: Anticoagulant rodenticides. World Health Organisation: Geneva.

External links

  • Link page to external chemical sources.

 
 

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