Abamectin

Abamectin
Clinical data
Other names	Avermectin B1 (CAS name), MK-936
ATCvet code	QP54AA02 (WHO) ;
Legal status
Legal status	AU: S5 (Caution) / S6;
Identifiers
	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;
CAS Number	71751-41-2 ;
ChemSpider	8095964 ;
UNII	5U8924T11H;
KEGG	D02777 ;
ChEMBL	ChEMBL1630577 ;
CompTox Dashboard (EPA)	DTXSID8023892 ;
ECHA InfoCard	100.113.437
Chemical and physical data
Formula	C48H72O14 (B1a); C47H70O14 (B1b)
3D model (JSmol)	;
	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;
	InChI 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 ; Key:IBSREHMXUMOFBB-JFUDTMANSA-N ;
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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 B_1a and B_1b forms comprising the majority of the fermentation.^[3] The non-proprietary name, abamectin, refers to a mixture of B_1a (~80%) and B_1b (~20%).^[3] Out of all the avermectins, abamectin is the only one that is used both in agriculture and pharmaceuticals.^[4]

^ 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): 526–531. doi:10.1038/nbt820. PMID 12692562.
^ ^a ^b Cite error: The named reference Campbell2012 was invoked but never defined (see the help page).
^ ^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.
^ Shoop WL, Mrozik H, Fisher MH (September 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.

[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): 526–531. doi:10.1038/nbt820. PMID 12692562.

[Campbell2012-2] Cite error: The named reference Campbell2012 was invoked but never defined (see the help page).

[Jansson_1998-3] 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 (September 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.

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