Avermectin B1A | CAS# 65195-55-3 | Insecticide

Avermectin B1A
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574448

CAS#: 65195-55-3

Description: Avermectin B1A is a macrocyclic lactone disaccharide anthelmintic agent that binds to high and low affinity sites on the mammalian GABAA receptor. Binding to the high affinity site activates the receptor to increase chloride influx, while binding to the low affinity site blocks the channel. Avermectin B1a inhibits binding of the glycine receptor antagonist strychnine to membranes and the solubilized receptor from rat spinal cord. Formulations containing avermectin B1a (>80%) and avermectin B1b (~20%) are used in insecticides and veterinary anthelmintic formulas as abamectin.

Chemical Structure

Avermectin B1A

CAS# 65195-55-3

Instruction

Theoretical Analysis

MedKoo Cat#: 574448
Name: Avermectin B1A
CAS#: 65195-55-3
Chemical Formula: C48H72O14
Exact Mass: 872.49
Molecular Weight: 873.090
Elemental Analysis: C, 66.03; H, 8.31; O, 25.65

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 355	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Avermectin B1A

IUPAC/Chemical Name: A name could not be generated for this structure.

InChi Key: RRZXIRBKKLTSOM-XPNPUAGNSA-N

InChi Code: 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

SMILES Code: C/C([C@@H](O[C@@]1([H])C[C@H](OC)[C@@H](O[C@]2([H])O[C@@H](C)[C@H](O)[C@@H](OC)C2)[C@H](C)O1)[C@@H](C)/C=C/C=C(CO3)/[C@@]([C@@]3([H])[C@H](O)C(C)=C4)(O)[C@]4([H])C5=O)=C\C[C@]6([H])C[C@@](O5)([H])C[C@]7(C=C[C@H](C)[C@]([C@@H](C)CC)([H])O7)O6

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 873.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hao Y, You Y, Chen Z, Li J, Liu G, Wen Y. Avermectin B1a production in Streptomyces avermitilis is enhanced by engineering aveC and precursor supply genes. Appl Microbiol Biotechnol. 2022 Mar;106(5-6):2191-2205. doi: 10.1007/s00253-022-11854-w. Epub 2022 Mar 8. PMID: 35258669.

2: Du Y, Shao Z, Xu Q, Li Z, Shao X. Azobenzene-Avermectin B1a Derivatives for Optical Modulation of Insect Behaviors. J Agric Food Chem. 2021 Dec 29;69(51):15530-15537. doi: 10.1021/acs.jafc.1c05036. Epub 2021 Dec 16. PMID: 34914386.

3: Yamashita S, Hayashi D, Nakano A, Hayashi Y, Hirama M. Total synthesis of avermectin B1a revisited. J Antibiot (Tokyo). 2016 Jan;69(1):31-50. doi: 10.1038/ja.2015.47. Epub 2015 Sep 9. PMID: 26350782.

4: Food Safety Commission of Japan. Abamectin:Avermectin (Pesticides). Food Saf (Tokyo). 2016 Mar 30;4(1):30-31. doi: 10.14252/foodsafetyfscj.2016004s. PMID: 32231902; PMCID: PMC6989155.

5: Huang J, Casida JE. 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. PMID: 9103505.

6: Fritz LC, Wang CC, Gorio A. Avermectin B1a irreversibly blocks postsynaptic potentials at the lobster neuromuscular junction by reducing muscle membrane resistance. Proc Natl Acad Sci U S A. 1979 Apr;76(4):2062-6. doi: 10.1073/pnas.76.4.2062. PMID: 287043; PMCID: PMC383534.

7: Graham D, Pfeiffer F, Betz H. Avermectin B1a inhibits the binding of strychnine to the glycine receptor of rat spinal cord. Neurosci Lett. 1982 Apr 16;29(2):173-6. doi: 10.1016/0304-3940(82)90349-4. PMID: 6283439.

8: Wang S, Bo Y, Chen J, Zhou X, Li W, Liang J, Dong M. Effects of heavy-ion beam irradiation on avermectin B1a and its analogues production by Streptomyces avermitilis. Eng Life Sci. 2018 Sep 12;18(10):711-720. doi: 10.1002/elsc.201800094. PMID: 32624865; PMCID: PMC6999553.

9: Kass IS, Wang CC, Walrond JP, Stretton AO. Avermectin B1a, a paralyzing anthelmintic that affects interneurons and inhibitory motoneurons in Ascaris. Proc Natl Acad Sci U S A. 1980 Oct;77(10):6211-5. doi: 10.1073/pnas.77.10.6211. PMID: 6255481; PMCID: PMC350245.

10: Paul SM, Skolnick P, Zatz M. Avermectin B1a: an irreversible activator of the gamma-aminobutyric acid-benzodiazepine-chloride-ionophore receptor complex. Biochem Biophys Res Commun. 1980 Sep 30;96(2):632-8. doi: 10.1016/0006-291x(80)91402-3. PMID: 6252889.

11: Olsen RW, Snowman AM. Avermectin B1a modulation of gamma-aminobutyric acid/benzodiazepine receptor binding in mammalian brain. J Neurochem. 1985 Apr;44(4):1074-82. doi: 10.1111/j.1471-4159.1985.tb08727.x. PMID: 2983026.

12: Pong SS, DeHaven R, Wang CC. A comparative study of avermectin B1a and other modulators of the gamma-aminobutyric acid receptor . chloride ion channel complex. J Neurosci. 1982 Jul;2(7):966-71. doi: 10.1523/JNEUROSCI.02-07-00966.1982. PMID: 6284889; PMCID: PMC6564392.

13: Sun Y, Diao X, Zhang Q, Shen J. Bioaccumulation and elimination of avermectin B1a in the earthworms (Eisenia fetida). Chemosphere. 2005 Jul;60(5):699-704. doi: 10.1016/j.chemosphere.2005.01.044. Epub 2005 Feb 26. PMID: 15963808.

14: Supavilai P, Karobath M. In vitro modulation by avermectin B1a of the GABA/benzodiazepine receptor complex of rat cerebellum. J Neurochem. 1981 Mar;36(3):798-803. doi: 10.1111/j.1471-4159.1981.tb01664.x. PMID: 6259289.

15: Lofgren CS, Williams DF. Avermectin B1a: highly potent inhibitor of reproduction by queens of the red imported fire ant (Hymenoptera: Formicidae). J Econ Entomol. 1982 Oct;75(5):798-803. doi: 10.1093/jee/75.5.798. PMID: 7175003.

16: Sigel E, Baur R. Effect of avermectin B1a on chick neuronal gamma- aminobutyrate receptor channels expressed in Xenopus oocytes. Mol Pharmacol. 1987 Dec;32(6):749-52. PMID: 2447480.

17: Pong SS, Wang CC. Avermectin B1a modulation of gamma-aminobutyric acid receptors in rat brain membranes. J Neurochem. 1982 Feb;38(2):375-9. doi: 10.1111/j.1471-4159.1982.tb08639.x. PMID: 6286885.

18: Wang SY, Bo YH, Zhou X, Chen JH, Li WJ, Liang JP, Xiao GQ, Wang YC, Liu J, Hu W, Jiang BL. Significance of Heavy-Ion Beam Irradiation-Induced Avermectin B1a Production by Engineered Streptomyces avermitilis. Biomed Res Int. 2017;2017:5373262. doi: 10.1155/2017/5373262. Epub 2017 Jan 24. PMID: 28243599; PMCID: PMC5294878.

19: Mellin TN, Busch RD, Wang CC. Postsynaptic inhibition of invertebrate neuromuscular transmission by avermectin B1a. Neuropharmacology. 1983 Jan;22(1):89-96. doi: 10.1016/0028-3908(83)90265-4. PMID: 6302548.

20: Hou Z, Liang X, Du L, Su F, Su W. Quantitative determination and validation of avermectin B1a in commercial products using quantitative nuclear magnetic resonance spectroscopy. Magn Reson Chem. 2014 Sep;52(9):480-5. doi: 10.1002/mrc.4098. Epub 2014 Jun 18. PMID: 24943110.

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