Abamectin

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Abamectin
Avermectins.png
Abamectin B1a.png Abamectin B1b.png
Clinical data
Other namesAvermectin B1 (CAS name), MK-936
ATCvet code
Legal status
Legal status
  • AU: S5 (Caution) / S6
Identifiers
  • Mixture of:
    (10E,14E,16E)-(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)-6′-[(S)-sec-butyl]-21,24-dihydroxy-5′,11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2′-(5′,6′-dihydro-2′H-pyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
    and
    (10E,14E,16E)-(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)-21,22-dihydroxy-6′-isopropyl-5′,11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2′-(5′,6′-dihydro-2′H-pyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
CAS Number
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.113.437 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C 48 H 72 O 14 (B1a)
C47H70O14 (B1b)
3D model (JSmol)
    • CC[C@H](C)[C@H]1O[C@@]2(C[C@@H]3C[C@@H](C\C=C(/C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C\6/CO[C@@H]7[C@H](O)C(=C[C@@H](C(=O)O3)[C@]67O)C)O2)C=C[C@@H]1C
    • InChI=1S/C48H72O14.C47H70O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38;1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18-34(45(50)57-33)47(31,44)51)58-38-21-36(53-10)43(30(8)56-38)59-37-20-35(52-9)40(49)29(7)55-37/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3;11-14,16-18,24-25,27,29-30,32-44,48-49,51H,15,19-23H2,1-10H3/b13-12+,27-15+,32-14+;12-11+,26-14+,31-13+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+;25-,27-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43-,44+,46+,47+/m00/s1 Yes check.svgY
    • Key:IBSREHMXUMOFBB-JFUDTMANSA-N Yes check.svgY
     X mark.svgNYes check.svgY  (what is this?)    (verify)

    Abamectin (also called avermectin B1) is a widely used insecticide and anthelmintic. Abamectin, is a member of the avermectin family and is a natural fermentation product of soil dwelling [1] actinomycete Streptomyces avermitilis . [2] Abamectin differs from ivermectin, the popular member of the avermectin family, by a double bond between carbons 22 and 25. [2] Fermentation of Streptomyces avermitilis yields eight closely related avermectin homologs, with the B1a and B1b forms comprising the majority of the fermentation. [3] The non-proprietary name, abamectin, refers to a mixture of B1a (~80%) and B1b (~20%). [3] Out of all the avermectins, abamectin is the only one that is used both in agriculture and pharmaceuticals. [4]

    Contents

    Mode of Action

    Avermectins bind to the glutamate-gated chloride channels that are found in invertebrate nerve and muscle cells. [5] They cause hyperpolarization of these cells resulting in paralysis and death. [5] Mammals only possess glutamate-gated chloride channels in the brain and spinal cord and as the avermectins have a low affinity for other mammalian ligand-gated channels and do not usually cross the blood–brain barrier, they are very safe for mammals. [6]

    History

    Avermectins were discovered in 1967 in fermentation broths of an actinomycete culture received from the Kitasato Institute in Japan, following an intensive search designed to find natural products with anthelmintic activity. [7] It was not until 1985 ivermectin was first used to treat infections with Onchocerca volvulus (onchocerciasis or river blindness) in humans by the United Nations. [8] The discoverers of avermectin, William C. Campbell and Satoshi Ōmura, shared the 2015 Nobel Prize in Physiology or Medicine. [9]

    Activity

    Abamectin is an insecticide as well as an acaricide (miticide) [2] and a nematicide. It is also used to control fire ants. [10] Abamectin is provided orally to horses for deworming them. [11]

    Use

    Abamectin is also used as a veterinary antihelmintic. Resistance to abamectin-based antihelmintics, although a growing problem, is not as common as to other classes of veterinary antihelmintics.[ citation needed ] The benzoate salt emamectin benzoate is also used as an insecticide. Avermectins have been used to treat various ailments caused by parasites in both humans and animals. [12] Avermectins including abamectin were studied for use as anti alcohol therapies. [13] [12] Recently, ivermectin is being studied for use as an anti inflammatory agent. [14]

    Environmental Fate

    Abamectin degrades rapidly when exposed to light (photodegradation) on plant surfaces, in soil, dung and water. [15] Half life of Avermectins (including abamectin) varies between 0.5 and 23 days depending on the rate and substrate (water, soil, faeces or plant). [16] Avermectin B1a applied at 0.02-0.03 lb ai/acre (50% higher than recommended rates) resulted in very low residue. [17]

    Non targets

    Abamectin is highly toxic to bees either if they consume or come in direct contact. [18] However, plant parts exposed to abamectin spraying did not cause toxicity to bees 24 hours after treatment. [18] [19] The reason for lower toxicity in foliage is due to a half life <24 hours in plant surfaces. [16]

    Trade names

    Trade names include Abba, Abathor, Affirm, Agri-Mek, Avid, Dynamec, Epi-Mek, Genesis Horse Wormer, Reaper, Termictine 5%, Vertimec, CAM-MEK 1.8% EC (cam for agrochemicals), Zephyr and Cure 1.8 EC.[ citation needed ]

    Related Research Articles

    <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 (for example, foxes, coyotes, cougars and wombats. 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.

    <i>Streptomyces</i> Genus of bacteria

    Streptomyces is the largest genus of Actinomycetota, and the type genus of the family Streptomycetaceae. Over 700 species of Streptomyces bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, and have very large genomes with high GC content. Found predominantly in soil and decaying vegetation, most streptomycetes produce spores, and are noted for their distinct "earthy" odor that results from production of a volatile metabolite, geosmin. Different strains of the same species may colonize very diverse environments.

    <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">Doramectin</span> Chemical compound

    Doramectin, sold under the brand name Dectomax among others, is a veterinary medication approved by the US Food and Drug Administration (FDA) for the treatment of parasites such as gastrointestinal roundworms, lungworms, eyeworms, grubs, sucking lice, and mange mites in cattle. It is available as a generic medication. It is available as a combination with levamisole under the brand name Valcor.

    <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.

    <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">Avermectin</span> Drugs to treat parasitic worms and insect pests

    The avermectins are a series of drugs and pesticides used to treat parasitic worm infestations and to reduce insect pests. They are a group of 16-membered macrocyclic lactone derivatives with potent anthelmintic and insecticidal properties. These naturally occurring compounds are generated as fermentation products by Streptomyces avermitilis, a soil actinomycete. Eight different avermectins were isolated in four pairs of homologue compounds, with a major (a-component) and minor (b-component) component usually in ratios of 80:20 to 90:10. Avermectin B1, a mixture of B1a and B1b, is the drug and pesticide abamectin. Other anthelmintics derived from the avermectins include ivermectin, selamectin, doramectin, eprinomectin.

    <span class="mw-page-title-main">Spinosad</span> Medication

    Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus Saccharopolyspora was discovered in 1985 in isolates from crushed sugarcane. The bacteria produce yellowish-pink aerial hyphae, with bead-like chains of spores enclosed in a characteristic hairy sheath. This genus is defined as aerobic, Gram-positive, nonacid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a nonoperational sugar mill rum still in the Virgin Islands. Spinosad is a mixture of chemical compounds in the spinosyn family that has a generalized structure consisting of a unique tetracyclic ring system attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose). Spinosad is relatively nonpolar and not easily dissolved in water.

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

    Thelaziasis is the term for infestation with parasitic nematodes of the genus Thelazia. The adults of all Thelazia species discovered so far inhabit the eyes and associated tissues of various mammal and bird hosts, including humans. Thelazia nematodes are often referred to as "eyeworms".

    The milbemycins are a group of macrolides chemically related to the avermectins and were first isolated in 1972 from Streptomyces hygroscopicus. They are used in veterinary medicine as antiparasitic agents against worms, ticks and fleas.

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

    Milbemycin oxime, sold under the brand name Interceptor among others, is a veterinary medication from the group of milbemycins, used as a broad spectrum antiparasitic. It is active against worms (anthelmintic) and mites (miticide).

    <span class="mw-page-title-main">Anthelmintic</span> Antiparasitic drugs that expel parasitic worms (helminths) from the body

    Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may also be called vermifuges or vermicides. Anthelmintics are used to treat people who are infected by helminths, a condition called helminthiasis. These drugs are also used to treat infected animals.

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

    Emamectin is the 4″-deoxy-4″-methylamino derivative of abamectin, a 16-membered macrocyclic lactone produced by the fermentation of the soil actinomycete Streptomyces avermitilis. It is generally prepared as the salt with benzoic acid, emamectin benzoate, which is a white or faintly yellow powder. Emamectin is widely used in the US and Canada as an insecticide because of its chloride channel activation properties.

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

    Oxfendazole is a broad spectrum benzimidazole anthelmintic. Its main use is for protecting livestock against roundworm, strongyles and pinworms. Oxfendazole is the sulfoxide metabolite of fenbendazole.

    Streptomyces avermitilis is a species of bacteria in the genus Streptomyces. This bacterium was discovered by Satoshi Ōmura in Shizuoka Prefecture, Japan.

    <span class="mw-page-title-main">Satoshi Ōmura</span> Japanese biochemist

    Satoshi Ōmura is a Japanese biochemist. He is known for the discovery and development of hundreds of pharmaceuticals originally occurring in microorganisms. In 2015, he was awarded the Nobel Prize in Physiology or Medicine jointly with William C. Campbell for their role in the discovery of avermectins and ivermectin, the world's first endectocide and a safe and highly effective microfilaricide. It is believed that the large molecular size of ivermectin prevents it from crossing the blood/aqueous humour barrier, and renders the drug an important treatment of helminthically-derived blindness.

    <span class="mw-page-title-main">William C. Campbell (scientist)</span> Nobel Winner, co-inventor of ivermectin

    William Cecil Campbell is an Irish biologist and parasitologist with United States citizenship, known for his work in discovering a novel therapy against infections caused by roundworms, for which he was jointly awarded the 2015 Nobel Prize in Physiology or Medicine. He helped to discover a class of drugs called avermectins, whose derivatives have been shown to have "extraordinary efficacy" in treating River blindness and Lymphatic filariasis, among other parasitic diseases affecting animals and humans. Campbell worked at the Merck Institute for Therapeutic Research 1957–1990, and is currently a research fellow emeritus at Drew University.

    Streptomyces microflavus is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces microflavus produces nemadectin, fattiviracin A1, milbemycin and deoxyuridines. Streptomyces microflavus also produces the ionophore valinomycin. Streptomyces microflavus is also known to cause potato common scab disease in Korea.

    <span class="mw-page-title-main">Eprinomectin</span> Veterinary anti-parasitic medication

    Eprinomectin is an avermectin used as a veterinary topical endectocide. It is a mixture of two chemical compounds, eprinomectin B1a and B1b.

    <span class="mw-page-title-main">Carlos Lanusse</span> Argentinean pharmacology researcher

    Carlos E. Lanusse is an Argentine scientist and a professor of Pharmacology. He is the Director of the Veterinary Research Center and the Science and Technology Center of the Argentina National Council of Research in Tandil.

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    Further reading