Avermectin B1a

Names

[ Name ]:
Avermectin B1a

[Synonym ]:
5-O-Demethyl Antibiotic C 076A1a
Abamectinum [Latin]
Abamectin B1a
AVERMECTIN B1A
(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-Butan-2-yl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-5,6-dihydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.1.0]pentacosa[10,14,16,22]tetraen]-12'-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
Abamectine [French]
[3H]-Abamectin B1a
(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-5,11',13',22'-tetramethyl-5,6-dihydro-2'H-spiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.1.0]pentacosa[10,14,16,22]tetraen]-2'-one
(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-5,6-dihydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.1.0]pentacosa[10,14,16,22]tetraen]-12'-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
Abamectin komponente B1a
22,23-dihydroavermectinh B1a
abamectin component B1a
Avermectin B(1)a
Abamectina [Spanish]
(2aE,4E,5'S,6S,6'R,7S,8E,11R,13S,15S,17aR,20R,20aR,20bS)-6'-[(2S)-butan-2-yl]-20,20b-dihydroxy-5',6,8,19-tetramethyl-17-oxo-5',6,6',10,11,14,15,17,17a,20,20a,20b-dodecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadecine-13,2'-pyran]-7-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
(2aE,4E,8E)-(5'S,6S,6'R,7S,11R,13S,15S,17aR,20R,20aR,20bS)-6'-((S)-sec-Butyl)-5',6,6',7,10,11,14,15,17a,20,20a,20b-dodecahydro-20,20b-dihydroxy-5',6,8,19-tetramethyl-17-oxospiro(11,15-methano-2H,13H,17H-furo(4,3,2-pq)(2,6)benzodioxacyclooctadecin-13,2'-(2H)pyran)-7-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
Vertimec(R)018SC
Caswell No. 063AB
(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-5,6-dihydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.1. 0]pentacosa[10,14,16,22]tetraen]-12'-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-5,6-dihydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.1.0]pentacosa[10,14,16,22]tetraen]-12'-yl-2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
Antibiotic C 076B1a

Biological Activity

[Description]:

Avermectin B1a is an antiparasitic agent that paralyzes nematodes without causing hypercontraction or flaccid paralysis.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[In Vitro]

[3H]AVM B1a preferentially binds to synaptic membranes from several regions of rat brain. [3H]AVM B1a specific binding to intact monolayers of granule cells increases rapidly with time of incubation and reaches equilibrium after approximately 20 min at 24°C. Higher concentrations of [3H]AVM B1a leads to markedly greater nonspecific binding, 60% at 25 nM. Various AVM analogs also produce concentration-dependent inhibition of [3H]AVM B1a binding in intact cerebellar neurons. AVM B1a and moxidectin are similar in potency (IC50 values, 120 and 126 nM, respectively)[3]. AVMB1a-stimulated chloride efflux from mouse brain synaptic vesicles results from the activation of GABA-insensitive chloride channels and that this action is distinct from their previously documented effects on GABA-gated chloride channels in mouse brain preparations[4].

[In Vivo]

Bacteria are significantly inhibited when the AVM B1a concentration is higher than 83.3 mg/kg, while fungi are less impaired in soil. Soil respiration is also inhibited by high concentration AVM B1a, which differs with soil types. The half lethal dosage (LD50) of AVM B1a to soil earthworm is estimated as 4.63 mg × cm2 in filter paper contact test, and as 24.13 and 17.06 mg/kg, respectively after treated 7 and 14 days in artificial soil[1]. Iin artificial soil, the LC50 of AVM B1a on earthworms are 24.1 mg/kg and 17.1 mg/kg, respectively, for 7 and 14 days. About 80.0% and 94.8% of the accumulated AVM B1a are eliminated respectively in two groups within 1 day after they are exposed to AVM B1a-free soil, but a trace amount of AVM B1a is found for a relative long time in earthworms[2].

[References]

[1]. Sun Y, et al. [Effects of avermectin B1a on soil microorganism and earthworm (Eisenia fetida)]. Ying Yong Sheng Tai Xue Bao. 2005 Nov;16(11):2140-3.

[2]. Sun Y, et al. Bioaccumulation and elimination of avermectin B1a in the earthworms (Eisenia fetida). Chemosphere. 2005 Jul;60(5):699-704.

[3]. Huang J, et al. 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. J Pharmacol Exp Ther. 1997 Apr;281(1):261-6.

[4]. Payne GT, et al. Activation of gamma-aminobutyric acid insensitive chloride channels in mouse brain synaptic vesicles by avermectin B1a. J Biochem Toxicol. 1991 Winter;6(4):283-92.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
940.9±65.0 °C at 760 mmHg

[ Melting Point ]:
157-162ºC

[ Molecular Formula ]:
C₄₈H₇₂O₁₄

[ Molecular Weight ]:
873.077

[ Flash Point ]:
268.1±27.8 °C

[ Exact Mass ]:
872.492188

[ PSA ]:
170.06000

[ LogP ]:
6.51

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.571

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CL1200000

CHEMICAL NAME :: Avermectin A1a, 5-O-demethyl-

CAS REGISTRY NUMBER :: 65195-55-3

LAST UPDATED :: 199706

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C48-H72-O14

MOLECULAR WEIGHT :: 873.20

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD20 - Lethal Dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 32,94,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 32,94,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 19 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 42,1786,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 32,94,1984

Safety Information

[ RIDADR ]:
UN 2588

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%