Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Abamectin: Difference between pages

{{short description|Insecticide and anti-parasitic worm chemical}}

{{Infobox drug

| verifiedrevid =

| IUPAC_name = '' of:''<br />(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<br />''and''<br />(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

| image = Avermectins.png

| width =

| imageL = Abamectin B1a.png

| widthL = 150

| imageR = Abamectin B1b.png

| widthR = 150

| tradename =

| pregnancy_category =

| legal_AU = S5

| legal_AU_comment = {{nbsp}}/{{nbsp}}S6

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| Jmol=None

| CAS_supplemental =

| ATC_supplemental =

| PubChem =

| DrugBank =

| ChEMBL = 1630577

<!--Chemical data-->

| chemical_formula = [[Carbon|C]]₄₈[[Hydrogen|H]]₇₂[[Oxygen|O]]₁₄ ()<br />C₄₇H₇₀O₁₄ ()

| =

| molecular_weight =

| smiles = 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

| synonyms = ([[Chemical Abstracts Service|CAS]] name), MK-936

'''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<ref>{{cite journal | vauthors = Ikeda H, Ishikawa J, Hanamoto A, Shinose M, Kikuchi H, Shiba T, Sakaki Y, Hattori M, Omura S | display-authors = 6 | title = Complete genome sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis | journal = Nature Biotechnology | volume = 21 | issue = 5 | pages = 526–531 | date = May 2003 | pmid = 12692562 | doi = 10.1038/nbt820 | doi-access = free }}</ref> [[Actinomycetales|actinomycete]] ''[[Streptomyces avermitilis]]''.<ref name="Campbell2012" /> Abamectin differs from [[ivermectin]], the popular member of the avermectin family, by a double bond between carbons 22 and 25.<ref name="Campbell2012" /> Fermentation of ''[[Streptomyces avermitilis]]'' yields eight closely related avermectin [[Homologous series|homologs]], with the B_1a and B_1b forms comprising the majority of the fermentation.<ref name="Jansson_1998">{{cite book | vauthors = Jansson RK, Dybas RA | chapter = Avermectins: Biochemical Mode of Action, Biological Activity and Agricultural Importance|date=1998 |title=Insecticides with Novel Modes of Action: Mechanisms and Application|pages=152–170| veditors = Ishaaya I, Degheele D |series=Applied Agriculture|place=Berlin, Heidelberg|publisher=Springer|language=en|doi=10.1007/978-3-662-03565-8_9|isbn=978-3-662-03565-8 }}</ref> The non-proprietary name, abamectin, refers to a mixture of B_1a (~80%) and B_1b (~20%).<ref name="Jansson_1998" /> Out of all the avermectins, abamectin is the only one that is used both in agriculture and pharmaceuticals.<ref>{{cite journal | vauthors = Shoop WL, Mrozik H, Fisher MH | title = Structure and activity of avermectins and milbemycins in animal health | journal = Veterinary Parasitology | volume = 59 | issue = 2 | pages = 139–156 | date = September 1995 | pmid = 7483237 | doi = 10.1016/0304-4017(94)00743-V }}</ref>

== Mode of Action ==

Avermectins bind to the glutamate-gated chloride channels that are found in invertebrate nerve and muscle cells.<ref name="Wolstenholme_2006">{{cite journal | vauthors = Wolstenholme AJ, Rogers AT | title = Glutamate-gated chloride channels and the mode of action of the avermectin/milbemycin anthelmintics | journal = Parasitology | volume = 131 Suppl | issue = S1 | pages = S85–S95 | date = 2006-03-29 | pmid = 16569295 | doi = 10.1017/S0031182005008218 | s2cid = 14474894 }}</ref> They cause hyperpolarization of these cells resulting in paralysis and death.<ref name="Wolstenholme_2006" /> 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.<ref>{{cite journal | vauthors = Omura S, Crump A | title = Ivermectin: panacea for resource-poor communities? | journal = Trends in Parasitology | volume = 30 | issue = 9 | pages = 445–455 | date = September 2014 | pmid = 25130507 | doi = 10.1016/j.pt.2014.07.005 | doi-access = free }}</ref>

==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.<ref>{{cite journal | vauthors = Lasota JA, Dybas RA | title = Avermectins, a novel class of compounds: implications for use in arthropod pest control | journal = Annual Review of Entomology | volume = 36 | issue = 1 | pages = 91–117 | date = 1991 | pmid = 2006872 | doi = 10.1146/annurev.en.36.010191.000515 }}</ref> 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.<ref>{{cite journal | vauthors = Crump A, Ōmura S | title = Ivermectin, 'wonder drug' from Japan: the human use perspective | journal = Proceedings of the Japan Academy. Series B, Physical and Biological Sciences | volume = 87 | issue = 2 | pages = 13–28 | date = 2011 | pmid = 21321478 | pmc = 3043740 | doi = 10.2183/pjab.87.13 | doi-access = free | bibcode = 2011PJAB...87...13C }}</ref> The discoverers of avermectin, [[William C. Campbell (scientist)|William C. Campbell]] and [[Satoshi Ōmura]], shared the 2015 [[Nobel Prize in Physiology or Medicine]].<ref>{{Cite web|title=The Nobel Prize in Physiology or Medicine 2015|url=https://www.nobelprize.org/prizes/medicine/2015/press-release/|access-date=2021-04-09|website=NobelPrize.org|language=en-US|archive-date=2021-02-09|archive-url=https://web.archive.org/web/20210209183747/https://www.nobelprize.org/prizes/medicine/2015/press-release/|url-status=live}}</ref>

==Activity==

Abamectin is an insecticide as well as an [[acaricide]] (miticide)<ref name="Campbell2012">{{cite book| vauthors = Campbell WC |title=Ivermectin and Abamectin|url=https://books.google.com/books?id=LAHaBwAAQBAJ&pg=PA304|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-3626-9|pages=304–}}</ref> and a [[nematicide]]. It is also used to control fire ants.<ref>{{Cite web|title=Ascend / Advance {{!}} Texas Imported Fire Ant Research and Management Project|url=https://fireant.tamu.edu/controlmethods/products/ascend_advance/|access-date=2021-04-08|website=fireant.tamu.edu|archive-date=2021-01-27|archive-url=https://web.archive.org/web/20210127205916/https://fireant.tamu.edu/controlmethods/products/ascend_advance/|url-status=live}}</ref> Abamectin is provided orally to horses for deworming them.<ref>{{Cite web|title=Equine Megastore - Horse Wormers|url=https://www.equine-mega-store.com/horse-wormer|access-date=2021-04-08|website=www.equine-mega-store.com}}</ref>

==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|date=November 2018}} 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.<ref name="El-Saber Batiha_2020">{{cite journal | vauthors = El-Saber Batiha G, Alqahtani A, Ilesanmi OB, Saati AA, El-Mleeh A, Hetta HF, Magdy Beshbishy A | title = Avermectin Derivatives, Pharmacokinetics, Therapeutic and Toxic Dosages, Mechanism of Action, and Their Biological Effects | journal = Pharmaceuticals | volume = 13 | issue = 8 | pages = 196 | date = August 2020 | pmid = 32824399 | pmc = 7464486 | doi = 10.3390/ph13080196 | doi-access = free }}</ref> [[Avermectin]]s including abamectin were studied for use as anti alcohol therapies.<ref>{{cite journal | vauthors = Yardley MM, Neely M, Huynh N, Asatryan L, Louie SG, Alkana RL, Davies DL | title = Multiday administration of ivermectin is effective in reducing alcohol intake in mice at doses shown to be safe in humans | journal = NeuroReport | volume = 25 | issue = 13 | pages = 1018–1023 | date = September 2014 | pmid = 25004078 | pmc = 4126080 | doi = 10.1097/wnr.0000000000000211 }}</ref><ref name="El-Saber Batiha_2020" /> Recently, ivermectin is being studied for use as an anti inflammatory agent.<ref>{{cite journal | vauthors = Ventre E, Rozières A, Lenief V, Albert F, Rossio P, Laoubi L, Dombrowicz D, Staels B, Ulmann L, Julia V, Vial E, Jomard A, Hacini-Rachinel F, Nicolas JF, Vocanson M | display-authors = 6 | title = Topical ivermectin improves allergic skin inflammation | journal = Allergy | volume = 72 | issue = 8 | pages = 1212–1221 | date = August 2017 | pmid = 28052336 | doi = 10.1111/all.13118 | s2cid = 4640628 }}</ref>

== Environmental Fate ==

Abamectin degrades rapidly when exposed to light (photodegradation) on plant surfaces, in soil, dung and water.<ref>{{cite journal | vauthors = Halley BA, VandenHeuvel WJ, Wislocki PG | title = Environmental effects of the usage of avermectins in livestock | journal = Veterinary Parasitology | volume = 48 | issue = 1–4 | pages = 109–125 | date = June 1993 | pmid = 8346626 | doi = 10.1016/0304-4017(93)90149-H }}</ref> Half life of Avermectins (including abamectin) varies between 0.5 and 23 days depending on the rate and substrate (water, soil, faeces or plant).<ref name="Eco-toxicological effects of the av">{{cite journal | vauthors = Bai SH, Ogbourne S | title = Eco-toxicological effects of the avermectin family with a focus on abamectin and ivermectin | journal = Chemosphere | volume = 154 | pages = 204–214 | date = July 2016 | pmid = 27058912 | doi = 10.1016/j.chemosphere.2016.03.113 | bibcode = 2016Chmsp.154..204B }}</ref> Avermectin B_1a applied at 0.02-0.03 lb ai/acre (50% higher than recommended rates) resulted in very low residue.<ref>{{Cite journal| vauthors = Moye HA, Malagodi MH, Yoh J, Leibee GL, Ku CC, Wislocki PG |date=1987|title=Residues of avermectin B1a in rotational crops and soils following soil treatment with [14C]avermectin B1a |journal=Journal of Agricultural and Food Chemistry|language=en|volume=35|issue=6|pages=859–864|doi=10.1021/jf00078a003|issn=0021-8561}}</ref>

== Non targets ==

Abamectin is highly toxic to bees either if they consume or come in direct contact.<ref name="Wislocki_1989">{{cite book | vauthors = Wislocki PG, Grosso LS, Dybas RA | chapter = Environmental Aspects of Abamectin Use in Crop Protection|date=1989 |title =Ivermectin and Abamectin|pages=182–200|place=New York, NY|publisher=Springer New York|isbn=978-1-4612-8184-9|doi=10.1007/978-1-4612-3626-9_13}}</ref> However, plant parts exposed to abamectin spraying did not cause toxicity to bees 24 hours after treatment.<ref name="Wislocki_1989" /><ref>{{cite journal | vauthors = Lumaret JP, Errouissi F, Floate K, Römbke J, Wardhaugh K | title = A review on the toxicity and non-target effects of macrocyclic lactones in terrestrial and aquatic environments | journal = Current Pharmaceutical Biotechnology | volume = 13 | issue = 6 | pages = 1004–1060 | date = May 2012 | pmid = 22039795 | pmc = 3409360 | doi = 10.2174/138920112800399257 }}</ref> The reason for lower toxicity in foliage is due to a half life <24 hours in plant surfaces.<ref name="Eco-toxicological effects of the av"/>

== 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|date=December 2022}}

== References ==

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite web | url = http://extoxnet.orst.edu/pips/abamecti.htm | title = Pesticide Information Profile: Abamectin | work = Pesticide Management Education Program | publication-date = June 1996 | publisher = Extension Toxicology Network (EXTOXNET) | archive-url = https://web.archive.org/web/20210223224949/http://extoxnet.orst.edu/pips/abamecti.htm | archive-date = 23 February 2021 }}

* {{cite web | url = http://www.farmchemicalsinternational.com/cropprotection/cpd/?op=cpdproductdetail&pid=20440 | work = Crop Protection Database | publisher = Farm Chemicals International | title = Learn more about abamectin | archive-url = https://web.archive.org/web/20110429030809/http://www.farmchemicalsinternational.com/cropprotection/cpd/?op=cpdproductdetail&pid=20440 | archive-date = 2011-04-29 }}

{{refend}}

{{Endectocides}}

{{Authority control}}

[[Category:Antiparasitic agents]]

[[Category:Insecticides]]

[[Category:Macrocycles]]

[[Category:Spiro compounds]]