Eprinomectin B1b

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Eprinomectin B1b
Category Others
Catalog number BBF-04245
CAS 133305-89-2
Molecular Weight 900.10
Molecular Formula C49H73NO14
Purity >99% by HPLC

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Description

It is a semi-synthetic analogue of avermectin B1b prepared by oxidation of the 4''-hydroxy moiety and reductive amination followed by acetylation. It is the minor component (<10%) of the commercial product for endo- and exo-parasite control, eprinomectin. It is a potent insecticide and acaricide.

Specification

Synonyms (4''R)-4''-(Acetylamino)-5-O-demethyl-25-de(1-methylpropyl)-4''-deoxy-25-(1-methylethyl)avermectin A1a; Eprinomectin component B1b
Storage Store at -20°C
IUPAC Name N-[(2S,3R,4S,6S)-6-[(2S,3S,4S,6R)-6-[(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-3,11',13',22'-tetramethyl-2'-oxo-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]-12'-yl]oxy-4-methoxy-2-methyloxan-3-yl]oxy-4-methoxy-2-methyloxan-3-yl]acetamide
Canonical SMILES CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)NC(=O)C)OC)OC)C)OC7(C4)C=CC(C(O7)C(C)C)C)O
InChI InChI=1S/C49H73NO14/c1-25(2)43-28(5)17-18-48(64-43)23-35-20-34(63-48)16-15-27(4)44(26(3)13-12-14-33-24-57-46-42(52)29(6)19-36(47(53)60-35)49(33,46)54)61-40-22-38(56-11)45(31(8)59-40)62-39-21-37(55-10)41(30(7)58-39)50-32(9)51/h12-15,17-19,25-26,28,30-31,34-46,52,54H,16,20-24H2,1-11H3,(H,50,51)/b13-12+,27-15+,33-14+/t26-,28-,30-,31-,34+,35-,36-,37-,38-,39-,40-,41+,42+,43+,44-,45-,46+,48+,49+/m0/s1
InChI Key WPNHOHPRXXCPRA-FZTOWWROSA-N
Source Semi-synthetic

Properties

Appearance White Solid
Antibiotic Activity Spectrum Parasites
Boiling Point 986.9°C at 760 mmHg
Density 1.24 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water

Reference Reading

1. Avermectin Derivatives, Pharmacokinetics, Therapeutic and Toxic Dosages, Mechanism of Action, and Their Biological Effects
Gaber El-Saber Batiha, Ali Alqahtani, Abdullah A Saati, Omotayo B Ilesanmi, Amany El-Mleeh, Helal F Hetta, Amany Magdy Beshbishy Pharmaceuticals (Basel) . 2020 Aug 17;13(8):196. doi: 10.3390/ph13080196.
Avermectins are a group of drugs that occurs naturally as a product of fermentingStreptomyces avermitilis, an actinomycetes, isolated from the soil. Eight different structures, including ivermectin, abamectin, doramectin, eprinomectin, moxidectin, and selamectin, were isolated and divided into four major components (A1a, A2a, B1a and B2a) and four minor components (A1b, A2b, B1b, and B2b). Avermectins are generally used as a pesticide for the treatment of pests and parasitic worms as a result of their anthelmintic and insecticidal properties. Additionally, they possess anticancer, anti-diabetic, antiviral, antifungal, and are used for treatment of several metabolic disorders. Avermectin generally works by preventing the transmission of electrical impulse in the muscle and nerves of invertebrates, by amplifying the glutamate effects on the invertebrates-specific gated chloride channel. Avermectin has unwanted effects or reactions, especially when administered indiscriminately, which include respiratory failure, hypotension, and coma. The current review examines the mechanism of actions, biosynthesis, safety, pharmacokinetics, biological toxicity and activities of avermectins.

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