ABAMECTIN B1A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C48H72O14
Molecular Weight	873.0769
Optical Activity	UNSPECIFIED
Defined Stereocenters	20 / 20
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@](C)(CC)[C@@]1([H])O[C@@]2(C[C@@H]3C[C@@]([H])(C\C=C(C)\[C@@H](O[C@@]4([H])C[C@H](OC)[C@@]([H])(O[C@@]5([H])C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C6/CO[C@]7([H])[C@H](O)C(C)=C[C@@]([H])(C(=O)O3)[C@]67O)O2)C=C[C@@H]1C

InChI

InChIKey=RRZXIRBKKLTSOM-XPNPUAGNSA-N

InChI=1S/C48H72O14/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/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9103505 | https://www.ncbi.nlm.nih.gov/pubmed/8346626

Avermectin B1a (AVM B1a), a widely used insecticide and acaricide, is reported to both activate and inhibit gamma-aminobutyric acidA (GABA(A)) receptor function in mammalian brain. Avermectin B1a is an antiparasitic agent that paralyzes nematodes without causing hypercontraction or flaccid paralysis. AVM B1a binds to two different sites in the GABA-gated chloride channel with dual effects, i.e., activating the channel on binding to the high-affinity site and blocking it on further binding to the low-affinity site.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9103505	Modulator 828

PubMed

Title	Date	PubMed
Environmental effects of the usage of avermectins in livestock.	1993 Jun	8346626
Avermectin B1a binds to high- and low-affinity sites with dual effects on the gamma-aminobutyric acid-gated chloride channel of cultured cerebellar granule neurons.	1997 Apr	9103505

Patents

Sample Use Guides

In Vitro Use Guide

Specific binding of [3H]AVM B1a in intact neuron cultures is time- and concentration-dependent and is displaceable by AVM analogs. Scatchard analysis of [3H]AVM B1a binding reveals high- and low-affinity sites with K(D) values of 5 and 815 nM, respectively. AVM B1a alters the binding of [3H]ethynylbicycloorthobenzoate at the noncompetitive blocker site in a biphasic manner; activation is evident with 10 to 300 nM AVM B1a after 5 to 10 min incubation and inhibition with an IC50 of 866 nM after 60 min incubation. Consistent with this observation, 36Cl- influx is stimulated by AVM B1a at 3 to 100 nM and inhibited at 1 to 3 uM. GABA-stimulated 36Cl- influx is completely blocked by both [3H]ethynylbicycloorthobenzoate and 12-ketoendrin (two GABA-gated chloride channel blockers) and AVM B1a at 1 to 1.5 uM. Also, 36Cl- influx induced by AVM B1a at 10 nM is suppressed by the two channel blockers.

Name

Type

Language

ABAMECTIN B1A

Common Name

English

ABAMECTIN COMPONENT B1A

Common Name

English

5-O-DEMETHYLAVERMECTIN A1A

Common Name

English

IVERMECTIN IMPURITY A [EP IMPURITY]

Common Name

English

AVERMECTIN B1A

Common Name

English

AVERMECTIN A1A, 5-O-DEMETHYL-

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

265-610-3