Fluralaner

Last updated
Fluralaner
Fluralaner structure.svg
Clinical data
Pronunciation /ˌflʊərəˈlænər/ FLOOR-ə-LAN-ər
Trade names Bravecto, Exzolt
Other names
  • A1443, AH252723
  • 4-[(5RS)-5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-1,2-oxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-o-toluamide
License data
Routes of
administration
By mouth
ATCvet code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 20–27%; [1] reduced in the fasted state [2]
Elimination half-life 9.3–16.2 days [3]
Identifiers
  • (±)-4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.215.812 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H17Cl2F6N3O3
Molar mass 556.29 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • Cc1cc(ccc1C(=O)NCC(=O)NCC(F)(F)F)C2=NOC(C2)(c3cc(cc(c3)Cl)Cl)C(F)(F)F
  • InChI=1S/C22H17Cl2F6N3O3/c1-11-4-12(2-3-16(11)19(35)31-9-18(34)32-10-21(25,26)27)17-8-20(36-33-17,22(28,29)30)13-5-14(23)7-15(24)6-13/h2-7H,8-10H2,1H3,(H,31,35)(H,32,34)
  • Key:MLBZKOGAMRTSKP-UHFFFAOYSA-N

Fluralaner (INN) [4] is a systemic insecticide and acaricide that is administered orally [5] or topically. [6] The U.S. Food and Drug Administration (FDA) approved it under the trade name Bravecto for flea treatment in dogs in May 2014 [7] and Bravecto Plus as a topical treatment for cats in November 2019, [8] with warnings about possible side effects in both species. [9] The EU approved the drug in February 2014. [10] Australia approved it for the treatment and prevention of ticks and fleas on dogs in January 2015. [11] For treating mites in chickens, a solution for use in drinking water is available under the name Exzolt; [12] it was introduced by the EU in 2017. [13]

Contents

Mode of action

Fluralaner inhibits γ-aminobutyric acid (GABA)-gated chloride channels (GABAA receptors) and L-glutamate-gated chloride channels (GluCls). [14] Potency of fluralaner is comparable to fipronil (a related GABA-antagonist insecticide and acaricide). [15]

Research

Fluralaner is being investigated to determine its ability to reduce the incidence of mosquito-borne diseases, [16] as well as bed bugs. [17] [18]

Related Research Articles

<span class="mw-page-title-main">Scabies</span> Human disease

Scabies is a contagious human skin infestation by the tiny (0.2–0.45 mm) mite Sarcoptes scabiei, variety hominis. The word is from Latin: scabere, lit. 'to scratch'. The most common symptoms are severe itchiness and a pimple-like rash. Occasionally, tiny burrows may appear on the skin. In a first-ever infection, the infected person usually develops symptoms within two to six weeks. During a second infection, symptoms may begin within 24 hours. These symptoms can be present across most of the body or just certain areas such as the wrists, between fingers, or along the waistline. The head may be affected, but this is typically only in young children. The itch is often worse at night. Scratching may cause skin breakdown and an additional bacterial infection in the skin.

<span class="mw-page-title-main">Mange</span> Type of skin disease caused by parasitic mites

Mange is a type of skin disease caused by parasitic mites. Because various species of mites also infect plants, birds and reptiles, the term "mange", or colloquially "the mange", suggesting poor condition of the skin and fur due to the infection, is sometimes reserved for pathological mite-infestation of nonhuman mammals. Thus, mange includes mite-associated skin disease in domestic mammals, in livestock, and in wild mammals. Severe mange caused by mites has been observed in wild bears. Since mites belong to the arachnid subclass Acari, another term for mite infestation is acariasis.

<span class="mw-page-title-main">Demodicosis</span> Medical condition

Demodicosis, also called Demodex folliculitis in humans and demodectic mange or red mange in animals, is caused by a sensitivity to and overpopulation of Demodex spp. as the host's immune system is unable to keep the mites under control.

<span class="mw-page-title-main">Ivermectin</span> Medication for parasite infestations

Ivermectin is an antiparasitic drug. After its discovery in 1975, its first uses were in veterinary medicine to prevent and treat heartworm and acariasis. Approved for human use in 1987, it is used to treat infestations including head lice, scabies, river blindness (onchocerciasis), strongyloidiasis, trichuriasis, ascariasis and lymphatic filariasis. It works through many mechanisms to kill the targeted parasites, and can be taken by mouth, or applied to the skin for external infestations. It belongs to the avermectin family of medications.

<span class="mw-page-title-main">Selamectin</span> Topical parasiticide for dogs and cats

Selamectin, sold under the brand name Revolution, among others, is a topical parasiticide and anthelminthic used on dogs and cats. It treats and prevents infections of heartworms, fleas, ear mites, sarcoptic mange (scabies), and certain types of ticks in dogs, and prevents heartworms, fleas, ear mites, hookworms, and roundworms in cats. It is structurally related to ivermectin and milbemycin. Selamectin is not approved for human use.

Poultry diseases occur in poultry, which are domesticated birds kept for their meat, eggs or feathers. Poultry species include the chicken, turkey, duck, goose and ostrich.

<span class="mw-page-title-main">Moxidectin</span> Chemical compound

Moxidectin is an anthelmintic drug used in animals to prevent or control parasitic worms (helminths), such as heartworm and intestinal worms, in dogs, cats, horses, cattle and sheep. Moxidectin kills some of the most common internal and external parasites by selectively binding to a parasite's glutamate-gated chloride ion channels. These channels are vital to the function of invertebrate nerve and muscle cells; when moxidectin binds to the channels, it disrupts neurotransmission, resulting in paralysis and death of the parasite.

<span class="mw-page-title-main">Ear mite</span> Common name of many species of mites that live in the ears of animals and humans

Ear mites are mites that live in the ears of animals and humans. The most commonly seen species in veterinary medicine is Otodectes cynotis. This species, despite its name, is also responsible for 90% of ear mite infections in felines.

<i>Cheyletiella</i> Genus of mites

Cheyletiella is a genus of mites that live on the skin surface of dogs, cats, and rabbits.

<span class="mw-page-title-main">Cat flea</span> Species of flea

The cat flea is an extremely common parasitic insect whose principal host is the domestic cat, although a high proportion of the fleas found on dogs also belong to this species. This is despite the widespread existence of a separate and well-established "dog" flea, Ctenocephalides canis. Cat fleas originated in Africa but can now be found globally. As humans began domesticating cats, the prevalence of the cat flea increased and it spread throughout the world.

<i>Dermanyssus gallinae</i> Species of mite

Dermanyssus gallinae is a haematophagous ectoparasite of poultry. It has been implicated as a vector of several major pathogenic diseases. Despite its common names, it has a wide range of hosts including several species of wild birds and mammals, including humans, where the condition it causes is called gamasoidosis. In both size and appearance, it resembles the northern fowl mite, Ornithonyssus sylviarum.

<span class="mw-page-title-main">Cat health</span> Health of domestic cats

The health of domestic cats is a well studied area in veterinary medicine.

<i>Rhipicephalus microplus</i> Species of tick

The Asian blue tick is an economically important tick that parasitises a variety of livestock and wild mammal species, especially cattle, on which it is the most economically significant ectoparasite in the world. It is known as the Australian cattle tick, southern cattle tick, Cuban tick, Madagascar blue tick, and Puerto Rican Texas fever tick.

<span class="mw-page-title-main">Pyriprole</span> Chemical compound

Pyriprole is for veterinary use on dogs against external parasites such as fleas and ticks.

<span class="mw-page-title-main">Metaflumizone</span> Chemical compound

Metaflumizone is a semicarbazone insecticide indicated for the veterinary treatment of fleas and ticks, marketed under the brand name ProMeris. A discontinued variant of ProMeris, called ProMeris Duo or Promeris for Dogs, was indicated for canine use and was a formulated blend of metaflumizone and amitraz. The metaflumizone-only formulation is waterproof and typically remain effective for 30–45 days in a cutaneous application at the base of the neck.

<span class="mw-page-title-main">Mites of domestic animals</span> Type of parasite of domestic animals

Mites that infest and parasitize domestic animals cause disease and loss of production. Mites are small invertebrates, most of which are free living but some are parasitic. Mites are similar to ticks and both comprise the order Acari in the phylum Arthropoda. Mites are highly varied and their classification is complex; a simple grouping is used in this introductory article. Vernacular terms to describe diseases caused by mites include scab, mange, and scabies. Mites and ticks have substantially different biology from, and are classed separately from, insects. Mites of domestic animals cause important types of skin disease, and some mites infest other organs. Diagnosis of mite infestations can be difficult because of the small size of most mites, but understanding how mites are adapted to feed within the structure of the skin is useful.

Flea treatments are procedures used to treat flea infestations in human or animal populations. They may treat both the itching caused by bites and may remove or kill the fleas themselves.

<span class="mw-page-title-main">Afoxolaner</span> Chemical compound used as an insecticide

Afoxolaner (INN) is an insecticide and acaricide that belongs to the isoxazoline chemical compound group.

<span class="mw-page-title-main">Lotilaner</span> Chemical compound

Lotilaner, sold under the brand name Xdemvy, is an ectoparasiticide (anti-parasitic) medication used for the treatment of blepharitis caused by infestation by Demodex. It is used as an eye drop.

<span class="mw-page-title-main">Sarolaner</span> Chemical compound

Sarolaner, sold under the brand name Simparica, is an ectoparasiticide veterinary medication for the treatment of flea and tick infestations in dogs. It is also used off-label to control sarcoptic mange and demodectic mange.

References

  1. 1 2 "Bravecto (fluralaner) for the Treatment and Prophylaxis of Arachnoenthomoses in Dogs. Full Prescribing Information" (PDF) (in Russian). Intervet GesmbH. Archived from the original (PDF) on 17 May 2018. Retrieved 14 November 2016.
  2. Walther FM, Allan MJ, Roepke RK, Nuernberger MC (March 2014). "The effect of food on the pharmacokinetics of oral fluralaner in dogs". Parasites & Vectors. 7 (1): 84. doi: 10.1186/1756-3305-7-84 . PMC   3975707 . PMID   24598049.
  3. "Bravecto (fluralaner) Flavored Chews for Dogs. Prescribing Information" (PDF). Intervet, Inc., a subsidiary of Merck & Company, In. Archived from the original (PDF) on 27 March 2019. Retrieved 14 November 2016.
  4. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 69" (PDF). WHO Drug Information. 27 (1): 59. 2013. Archived from the original (PDF) on November 14, 2016. Retrieved 14 November 2016.
  5. Walther FM, Allan MJ, Roepke RK, Nuernberger MC (March 2014). "Safety of fluralaner chewable tablets (Bravecto), a novel systemic antiparasitic drug, in dogs after oral administration". Parasites & Vectors. 7 (1): 87. doi: 10.1186/1756-3305-7-87 . PMC   3975339 . PMID   24606886.
  6. Ranjan S, Young D, Sun F (July 2018). "A single topical fluralaner application to cats and to dogs controls fleas for 12 weeks in a simulated home environment". Parasites & Vectors. 11 (1): 385. doi: 10.1186/s13071-018-2927-0 . PMC   6029119 . PMID   29970135.
  7. Lee J (21 May 2014). "New Flea/Tick Medication by Merck Just Approved: Bravecto". Archived from the original on 15 June 2018. Retrieved 3 November 2014.
  8. "BRAVECTO® PLUS (fluralaner and moxidectin topical solution) for Cats Receives Approval from US Food and Drug Administration". Merck Animal Health. 2019-11-15. Archived from the original on 2022-09-19. Retrieved 22 May 2021.
  9. Center for Veterinary Medicine (2020-07-31). "Fact Sheet for Pet Owners and Veterinarians about Potential Adverse Events Associated with Isoxazoline Flea and Tick Products". FDA. Archived from the original on 2021-05-22. Retrieved 22 May 2021.
  10. "MSD Animal Health receives EU approval for Bravecto". 19 February 2014. Archived from the original on 27 March 2019. Retrieved 3 Nov 2014.
  11. "Agricultural and Veterinary Chemicals" (PDF). Australian Pesticides and Veterinary Medicines Authority. 10 February 2015. Archived (PDF) from the original on 19 September 2022. Retrieved 14 February 2019.
  12. Imrie, Paul (2020-06-24). "Backyard poultry red mite treatment launches". Vet Times. Retrieved 2023-12-01.
  13. Brauneis, Maria D.; Zoller, Hartmut; Williams, Heike; Zschiesche, Eva; Heckeroth, Anja R. (2017). "The acaricidal speed of kill of orally administered fluralaner against poultry red mites (Dermanyssus gallinae) on laying hens and its impact on mite reproduction". Parasites & Vectors. 10 (1): 594. doi: 10.1186/s13071-017-2534-5 . PMC   5712167 . PMID   29197422.
  14. Gassel M, Wolf C, Noack S, Williams H, Ilg T (February 2014). "The novel isoxazoline ectoparasiticide fluralaner: selective inhibition of arthropod γ-aminobutyric acid- and L-glutamate-gated chloride channels and insecticidal/acaricidal activity". Insect Biochemistry and Molecular Biology. 45: 111–124. doi: 10.1016/j.ibmb.2013.11.009 . PMID   24365472.
  15. Asahi M, Kobayashi M, Matsui H, Nakahira K (January 2015). "Differential mechanisms of action of the novel γ-aminobutyric acid receptor antagonist ectoparasiticides fluralaner (A1443) and fipronil". Pest Management Science. 71 (1): 91–95. doi:10.1002/ps.3768. PMID   24591229.
  16. Miglianico M, Eldering M, Slater H, Ferguson N, Ambrose P, Lees RS, et al. (July 2018). "Repurposing isoxazoline veterinary drugs for control of vector-borne human diseases". Proceedings of the National Academy of Sciences of the United States of America. 115 (29): E6920–E6926. Bibcode:2018PNAS..115E6920M. doi: 10.1073/pnas.1801338115 . PMC   6055183 . PMID   29967151.
  17. Murez, Cara (1 December 2022). "Two veterinary drugs may help eliminate bedbugs". United Press International, Inc. Retrieved 3 December 2022.
  18. Sheele, Johnathan M. (2020). "A Preliminary Report Showing Spinosad and Fluralaner Are Able to Incapacitate Cimex lectularius L., the Common Bed Bug". Cureus. 12 (4): e7529. doi: 10.7759/cureus.7529 . PMC   7198093 . PMID   32377477. S2CID   216501793.