Abamectin

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Insecticide and anti-parasitic worm chemical

title: "Abamectin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antiparasitic-agents", "highly-toxic-chemical-substances", "insecticides", "macrocycles", "spiro-compounds"] description: "Insecticide and anti-parasitic worm chemical" topic_path: "general/antiparasitic-agents" source: "https://en.wikipedia.org/wiki/Abamectin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Insecticide and anti-parasitic worm chemical ::

::data[format=table title="Infobox drug"]

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid477236952
IUPAC_nameMixture 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
imageAvermectins.png
image_classskin-invert-image
width300
imageLAbamectin B1a.png
image_classLbg-transparent
widthL150
imageRAbamectin B1b.png
image_classRbg-transparent
widthR150
pregnancy_AU
legal_AUS5
legal_AU_comment/S6
legal_CA
legal_UK
legal_US
JmolNone
CAS_number_Ref
CAS_number71751-41-2
ATCvetyes
ATC_prefixP54
ATC_suffixAA02
DrugBank_Ref
ChemSpiderID_Ref
ChemSpiderID8095964
UNII_Ref
UNII5U8924T11H
KEGG_Ref
KEGGD02777
ChEMBL_Ref
ChEMBL1630577
chemical_formulaC48H72O14 (B1a)
C47H70O14 (B1b)
C
smilesCCC@H[C@H]1O[C@@]2(C[C@@H]3CC@@HO2)C=C[C@@H]1C
StdInChI_Ref
StdInChI1S/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
StdInChIKey_Ref
StdInChIKeyIBSREHMXUMOFBB-JFUDTMANSA-N
synonymsAvermectin B1 (CAS name), MK-936
::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477236952 | IUPAC_name = 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 | image = Avermectins.png | image_class = skin-invert-image | width = 300 | imageL = Abamectin B1a.png | image_classL = bg-transparent | widthL = 150 | imageR = Abamectin B1b.png | image_classR = bg-transparent | widthR = 150 | tradename = | pregnancy_AU = | pregnancy_category = | legal_AU = S5 | legal_AU_comment = /S6 | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | Jmol=None

| CAS_number_Ref = | CAS_number = 71751-41-2 | CAS_supplemental = | ATCvet = yes | ATC_prefix = P54 | ATC_suffix = AA02 | ATC_supplemental = | PubChem = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 8095964 | UNII_Ref = | UNII = 5U8924T11H | KEGG_Ref = | KEGG = D02777 | ChEMBL_Ref = | ChEMBL = 1630577

| chemical_formula = C48H72O14 (B1a) C47H70O14 (B1b) | C= | H= | N= | O= | molecular_weight = | smiles = CCC@H[C@H]1O[C@@]2(C[C@@H]3CC@@HO2)C=C[C@@H]1C | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = IBSREHMXUMOFBB-JFUDTMANSA-N | synonyms = Avermectin B1 (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 actinomycete Streptomyces avermitilis. Abamectin differs from ivermectin, the popular member of the avermectin family, by a double bond between carbons 22 and 23. Fermentation of Streptomyces avermitilis yields eight closely related avermectin homologs, with the B1a and B1b forms comprising the majority of the fermentation. The non-proprietary name, abamectin, refers to a mixture of B1a (~80%) and B1b (~20%). Out of all the avermectins, abamectin is the only one that is used both in agriculture and pharmaceuticals.

Mode of action

Avermectins bind to the glutamate-gated chloride channels that are found in invertebrate nerve and muscle cells. They cause hyperpolarization of these cells resulting in paralysis and death. 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.

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. 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. The discoverers of avermectin, William C. Campbell and Satoshi Ōmura, shared the 2015 Nobel Prize in Physiology or Medicine.

Activity

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

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. 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. Avermectins including abamectin were studied for use as anti alcohol therapies. Recently, ivermectin is being studied for use as an anti inflammatory agent.

Environmental fate

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

Non targets

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

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. Abamet from Rainbow

References

References

  1. (May 2003). "Complete genome sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis". Nature Biotechnology.
  2. (1998). "Insecticides with Novel Modes of Action: Mechanisms and Application". Springer.
  3. (September 1995). "Structure and activity of avermectins and milbemycins in animal health". Veterinary Parasitology.
  4. (2006-03-29). "Glutamate-gated chloride channels and the mode of action of the avermectin/milbemycin anthelmintics". Parasitology.
  5. (September 2014). "Ivermectin: panacea for resource-poor communities?". Trends in Parasitology.
  6. (1991). "Avermectins, a novel class of compounds: implications for use in arthropod pest control". Annual Review of Entomology.
  7. (2011). "Ivermectin, 'wonder drug' from Japan: the human use perspective". Proceedings of the Japan Academy. Series B, Physical and Biological Sciences.
  8. "The Nobel Prize in Physiology or Medicine 2015".
  9. (6 December 2012). "Ivermectin and Abamectin". Springer Science & Business Media.
  10. "Ascend / Advance {{!}} Texas Imported Fire Ant Research and Management Project".
  11. "Equine Megastore - Horse Wormers".
  12. (August 2020). "Avermectin Derivatives, Pharmacokinetics, Therapeutic and Toxic Dosages, Mechanism of Action, and Their Biological Effects". Pharmaceuticals.
  13. (September 2014). "Multiday administration of ivermectin is effective in reducing alcohol intake in mice at doses shown to be safe in humans". NeuroReport.
  14. (August 2017). "Topical ivermectin improves allergic skin inflammation". Allergy.
  15. (June 1993). "Environmental effects of the usage of avermectins in livestock". Veterinary Parasitology.
  16. (July 2016). "Eco-toxicological effects of the avermectin family with a focus on abamectin and ivermectin". Chemosphere.
  17. (1987). "Residues of avermectin B1a in rotational crops and soils following soil treatment with [14C]avermectin B1a". Journal of Agricultural and Food Chemistry.
  18. (1989). "Ivermectin and Abamectin". Springer New York.
  19. (May 2012). "A review on the toxicity and non-target effects of macrocyclic lactones in terrestrial and aquatic environments". Current Pharmaceutical Biotechnology.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

antiparasitic-agentshighly-toxic-chemical-substancesinsecticidesmacrocyclesspiro-compounds