Basic information Safety Supplier Related

Avermectin A1a, 5-O-demethyl-22,23-dihydro-

Basic information Safety Supplier Related

Avermectin A1a, 5-O-demethyl-22,23-dihydro- Basic information

Product Name:
Avermectin A1a, 5-O-demethyl-22,23-dihydro-
Synonyms:
  • 22,23-Dihydro-5-O-demethylavermectin A1a
  • 5-O-Demethyl-22,23-dihydroavermectin A1a
  • Dihydroavermectin B1a
  • Ivermectin B1a
  • IvermectinH2B1a
  • (2Ae,4E,5'S,6S,6'R,7S,8E,11R,13R,15S,17ar,20R,20ar,20bs)-20,20B-dihydroxy-5',6,8,19-tetramethyl-6'-[(1S)-1-methylpropyl]-17-oxo-3',4',5',6,6',10,11,14,15,17,17A,20,20A,20B-tetradecahydro-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-alpha-L-arabino-hexopyranosyl)-3-o-methyl-alpha-L-arabino-hexopyranoside
  • Avermectin A1a, 5-O-demethyl-22,23-dihydro-
  • Ivermectin Impurity 3
CAS:
71827-03-7
MF:
C48H74O14
MW:
875.09
EINECS:
276-046-2
Product Categories:
  • Organics
Mol File:
71827-03-7.mol
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Avermectin A1a, 5-O-demethyl-22,23-dihydro- Chemical Properties

Melting point:
155-157°
Boiling point:
717.97°C (rough estimate)
Density 
1.0683 (rough estimate)
refractive index 
1.6130 (estimate)
storage temp. 
Store at -20°C
solubility 
Soluble in DMSO
form 
solid
pka
12.42±0.70(Predicted)
color 
white
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Avermectin A1a, 5-O-demethyl-22,23-dihydro- Usage And Synthesis

Description

Ivermectin B1a is the main component (>80%) of the anthelmintic ivermectin, which also contains ivermectin B1b (<20%; ). It produces antiparasitic activity by binding to glutamate-gated chloride channels expressed on nematode neurons and pharyngeal muscle cells, inducing irreversible channel opening and very long-lasting hyperpolarization/depolarization of the neuron/muscle cell, thereby blocking further function (EC50 = 104 nM). Formulations containing ivermectin inhibit replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero/hSLAM cells.

Uses

Ivermectin B1a-D2 is a deuterium labelled analogue of Ivermectin B1a (I940815), which is a major component of Ivermectin (I940800), a semi-synthetic derivative of Abamectin; consists of a mixture of not less than 80% component B1a and not more than 20% component B1b. Antihelmintic (Onchocerca). An invitro inhibitor of SARS-CoV-2/ Covid-19.

Definition

ChEBI: A macrocyclic lactone that is avermectin B1a in which the double bond present in the spirocyclic ring system has been reduced to a single bond. It is the major component of ivermectin.

References

[1] j. wolsetnholme and a. t. rogers. glutamate-gated chloride channels and the mode of action of the avermectin/milbemycin anthelmintics. parasitology131 suppl, s85-s95 (2005).
[2] s. gaisser, l. kellenberger, a. l. kaja, et al. direct production of ivermectin-like drugs after domain exchange in the avermectin polyketide synthase of streptomyces avermitilis atcc31272. organic & biomolecular chemistry 1(16), 2840-2847 (2003).
[3] j. p. arena, k. k. liu, p. s. paress, et al. the mechanism of action of avermectins in caenorhabditis elegans: correlation between activation of glutamate-sensitive chloride current, membrane binding, and biological activity. journal of parasitology 81, 286-294 (1995).

Avermectin A1a, 5-O-demethyl-22,23-dihydro-Supplier

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