Ivermectin B1b

• CAT Number: R034932
• CAS Number: 70209-81-3
• Molecular Formula: C47H72O14
• Molecular Weight: 861.079
• Purity: ≥95%
• Synonyms: 5-O-Demethyl-25-de(1-methylpropyl)-22,23-dihydro-25-(1-methylethyl)avermectin A1a; Spiro[11,15-methano-2H,13H,17H-furo[4,3,2-pq][2,6]benzodioxacyclooctadecin-13,2’-[2H]pyran] Avermectin A1a Deriv.; 22,23-Dihydroavermectin B1b
• Storage: -20°C
• IUPAC Name: (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethyl-6'-propan-2-ylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
• InChI: InChI=1S/C47H72O14/c1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18-34(45(50)57-33)47(31,44)51)58-38-21-36(53-10)43(30(8)56-38)59-37-20-35(52-9)40(49)29(7)55-37/h11-14,18,24-25,27,29-30,32-44,48-49,51H,15-17,19-23H2,1-10H3/b12-11+,26-14+,31-13+/t25-,27-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43-,44+,46+,47+/m0/s1
• InChIKey: VARHUCVRRNANBD-PVVXTEPVSA-N
• SMILES: CC1CCC2(CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)OC1C(C)C

Ivermectin B1b (CAS 70209-81-3) is the minor component (<20%) of the anthelmintic ivermectin, which is mainly comprised of ivermectin B1a. 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.  Formulations containing ivermectin inhibit replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero/hSLAM cells.

Reference

1.Campbell, W. C., et al. "Ivermectin: a potent new antiparasitic agent." Science 221.4613 (1983): 823-828.
2.Wolstenholme, A. J., and A. T. Rogers. "Glutamate-gated chloride channels and the mode of action of the avermectin/milbemycin anthelmintics." Parasitology 131.S1 (2005): S85.
3.Arena, Joseph P., et al. "The mechanism of action of avermectins in Caenorhabditis elegans: correlation between activation of glutamate-sensitive chloride current, membrane binding, and biological activity." The Journal of parasitology (1995): 286-294.
4.Caly, Leon, et al. "The FDA-approved drug ivermectin inhibits the replication of SARS-CoV-2 in vitro." Antiviral research 178 (2020): 104787.