abamectin

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%).

Key facts

Drug.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-hexopyranosideand(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
Drug.image: Avermectins.png
Drug.image_class: skin-invert-image
Drug.width: 300
Drug.imageL: Abamectin B1a.png
Drug.image_classL: bg-transparent
Drug.widthL: 150
Drug.imageR: Abamectin B1b.png
Drug.image_classR: bg-transparent
Drug.widthR: 150
Drug.legal_AU: S5
Drug.legal_AU_comment: /S6
Drug.Jmol: None
Drug.CAS_number: 71751-41-2
Drug.ATCvet: yes
Drug.ATC_prefix: P54
Drug.ATC_suffix: AA02
Drug.ChemSpiderID: 8095964

via Wikipedia infobox

Chemical data

Formula: C95H142O28
Molecular weight: 1732.1 g/mol
IUPAC name: (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-butan-2-yl-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one;(1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethyl-2-propan-2-ylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
SMILES: CCC(C)[C@@H]1[C@H](C=C[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\C)C.C[C@H]1/C=C/C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4C[C@@H](C/C=C(/[C@H]1O[C@H]5C[C@@H]([C@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O)OC)OC)\C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C(C)C)C)O
InChIKey: IBSREHMXUMOFBB-MVGRHBATSA-N
Polar surface area: 340 Å²
H-bond donors: 6
H-bond acceptors: 28
Formal charge: 0

via PubChem

Research

1,304 papers

Abamectin as a pesticide for agricultural use.Acta Leidensia · 1990
Abamectin promotes behavior changes and liver injury in zebrafish.Chemosphere · 2023
Abamectin Causes Neurotoxicity in Zebrafish Embryos.International journal of molecular sciences · 2025
MRI brain findings of Abamectin toxic encephalopathy: a case report with review of literature.Emergency radiology · 2023
Abamectin exposure causes chronic toxicity and trypsin/chymotrypsin damages in Chironomus kiiensis Tokunaga (Diptera: Chironomidae).Pesticide biochemistry and physiology · 2024

via PubMed

Wikidata facts

Image: AvermectinB1aB1b.svg

Show 1 more fact

World Health Organisation international non-proprietary name: abamektin

Sources (5)

via Wikidata · CC0

~4 min read

Article

9 sections

Contents

Mode of action
History
Activity
Use
Environmental fate
Non targets
Trade names
References
Further reading

== 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.