Abamectin

 Abamectin 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 (also called Avermectin B1), differs from Ivermectin, the popular member of
the Avermectin family, by double bond on C-22-25.[2] 
 Fermentation of Streptomyces avermitilis yields 8 closely related Avermectin homologues out of
which B1 (a and b) forms the bulk of the fermentation.[3] 
 The non proprietary name, abamectin, is a combination of Bla (~ 80%) and B1b (~ 20%).[3] 
 Out of all the Avermectins, abamectin is the only one that is used both in agriculture and
pharmaceuticals.[4]

Mode of Action[edit]
 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[edit]
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 Onchocerca
volvulus (Onchocerciasis or River blindness) in humans by the United Nations. [8] Discoverers
of Avermectin, William C. Campbell and Satoshi Ōmura, shared the 2015 Nobel prize for
physiology or medicine.[9]

Activity[edit]
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[edit]
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[edit]
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[edit]
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.[20]

Trade names[edit]
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]

From Wikipedia, the free encyclopedia

Abamectin

Clinical data

Other names avermectin B1 (CAS name), MK-936

ATCvet code  QP54AA02 (WHO)

Legal status

Legal status  AU: S5 (Caution)  / S6

Identifiers

show

IUPAC name

CAS Number  71751-41-2 

ChemSpider  8095964 

UNII  5U8924T11H
 ECHA InfoCard 100.113.437 

Chemical and physical data

Formula C48H72O14 (B1a)

C47H70O14 (B1b)

References[edit]
1. ^ Ikeda H, Ishikawa J, Hanamoto A, Shinose M, Kikuchi H, Shiba T, et al. (May 2003). "Complete genome
sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis". Nature
Biotechnology. 21 (5): 526–31. doi:10.1038/nbt820. PMID 12692562.
2. ^ Jump up to:a b c Campbell WC (6 December 2012). Ivermectin and Abamectin. Springer Science & Business
Media. pp. 304–. ISBN 978-1-4612-3626-9.
3. ^ Jump up to:a b Jansson RK, Dybas RA (1998). "Avermectins: Biochemical Mode of Action, Biological Activity
and Agricultural Importance". In Ishaaya I, Degheele D (eds.). Insecticides with Novel Modes of Action:
Mechanisms and Application. Applied Agriculture. Berlin, Heidelberg: Springer. pp. 152–
170. doi:10.1007/978-3-662-03565-8_9. ISBN 978-3-662-03565-8.
4. ^ Shoop WL, Mrozik H, Fisher MH (1995). "Structure and activity of avermectins and milbemycins in animal
health". Veterinary Parasitology. 59 (2): 139–156. doi:10.1016/0304-4017(94)00743-V. PMID 7483237.
5. ^ Jump up to:a b Wolstenholme AJ, Rogers AT (2006-03-29). "Glutamate-gated chloride channels and the mode of
action of the avermectin/milbemycin anthelmintics". Parasitology. 131 Suppl (S1): S85-
95. doi:10.1017/S0031182005008218. PMID 16569295. S2CID 14474894.
6. ^ Omura S, Crump A (September 2014). "Ivermectin: panacea for resource-poor communities?". Trends in
Parasitology. 30 (9): 445–55. doi:10.1016/j.pt.2014.07.005. PMID 25130507.
7. ^ Lasota JA, Dybas RA (1991). "Avermectins, a novel class of compounds: implications for use in arthropod pest
control". Annual Review of Entomology. 36 (1): 91–
117. doi:10.1146/annurev.en.36.010191.000515. PMID 2006872.
8. ^ Crump A, Ōmura S (2011). "Ivermectin, 'wonder drug' from Japan: the human use perspective". Proceedings
of the Japan Academy. Series B, Physical and Biological Sciences. 87 (2): 13–
28. Bibcode:2011PJAB...87...13C. doi:10.2183/pjab.87.13. PMC 3043740. PMID 21321478.
9. ^ "The Nobel Prize in Physiology or Medicine 2015". NobelPrize.org. Archived from the original on 2021-02-09.
Retrieved 2021-04-09.
10. ^ "Ascend / Advance | Texas Imported Fire Ant Research and Management
Project". fireant.tamu.edu. Archived from the original on 2021-01-27. Retrieved 2021-04-08.
11. ^ "Equine Megastore - Horse Wormers". www.equine-mega-store.com. Retrieved 2021-04-08.
12. ^ Jump up to:a b El-Saber Batiha G, Alqahtani A, Ilesanmi OB, Saati AA, El-Mleeh A, Hetta HF, Magdy Beshbishy
A (August 2020). "Avermectin Derivatives, Pharmacokinetics, Therapeutic and Toxic Dosages, Mechanism of
Action, and Their Biological Effects". Pharmaceuticals. 13 (8):
196. doi:10.3390/ph13080196. PMC 7464486. PMID 32824399.
13. ^ Yardley MM, Neely M, Huynh N, Asatryan L, Louie SG, Alkana RL, Davies DL (September 2014). "Multiday
administration of ivermectin is effective in reducing alcohol intake in mice at doses shown to be safe in
humans". NeuroReport. 25 (13): 1018–
23. doi:10.1097/wnr.0000000000000211. PMC 4126080. PMID 25004078.
14. ^ Ventre E, Rozières A, Lenief V, Albert F, Rossio P, Laoubi L, et al. (August 2017). "Topical ivermectin
improves allergic skin inflammation". Allergy. 72 (8): 1212–
1221. doi:10.1111/all.13118. PMID 28052336. S2CID 4640628.
15. ^ Halley BA, VandenHeuvel WJ, Wislocki PG (1993). "Environmental effects of the usage of avermectins in
livestock". Veterinary Parasitology. 48 (1–4): 109–125. doi:10.1016/0304-4017(93)90149-H. PMID 8346626.
16. ^ Bai SH, Ogbourne S (July 2016). "Eco-toxicological effects of the avermectin family with a focus on abamectin
and ivermectin". Chemosphere. 154: 204–
214. Bibcode:2016Chmsp.154..204B. doi:10.1016/j.chemosphere.2016.03.113. PMID 27058912.
17. ^ Moye HA, Malagodi MH, Yoh J, Leibee GL, Ku CC, Wislocki PG (1987). "Residues of avermectin B1a in
rotational crops and soils following soil treatment with [14C]avermectin B1a". Journal of Agricultural and
Food Chemistry. 35 (6): 859–864. doi:10.1021/jf00078a003. ISSN 0021-8561.
18. ^ Jump up to:a b Wislocki, P. G.; Grosso, L. S.; Dybas, R. A. (1989), "Environmental Aspects of Abamectin Use in
Crop Protection", Ivermectin and Abamectin, New York, NY: Springer New York, pp. 182–
200, doi:10.1007/978-1-4612-3626-9_13, ISBN 978-1-4612-8184-9, retrieved 2021-04-09
19. ^ Lumaret, Jean-Pierre; Errouissi, Faiek; Floate, Kevin; Rombke, Jorg; Wardhaugh, Keith (2012-04-01). "A
Review on the Toxicity and Non-Target Effects of Macrocyclic Lactones in Terrestrial and Aquatic
 Environments". Current Pharmaceutical Biotechnology. 13 (6): 1004–
1060. doi:10.2174/138920112800399257. ISSN 1389-2010. PMC 3409360. PMID 22039795.
20. ^ Bai, Shahla Hosseini; Ogbourne, Steven (2016). "Eco-toxicological effects of the avermectin family with a
focus on abamectin and ivermectin". Chemosphere. 154: 204–
214. Bibcode:2016Chmsp.154..204B. doi:10.1016/j.chemosphere.2016.03.113. PMID 27058912.

Further reading[edit]
 "Pesticide Information Profile: Abamectin". Pesticide Management Education Program. Extension Toxicology
Network (EXTOXNET). June 1996. Archived from the original on 23 February 2021.
 "Learn more about abamectin". Crop Protection Database. Farm Chemicals International. Archived from the
original on 2011-04-29.