Ivermectin

• CAT Number: A000480
• CAS Number: 70288-86-7
• Molecular Formula: C48H74O14
• Molecular Weight: 875.09
• Purity: ≥95%
• Target: P2X purinergic receptor
• Solubility: >43.8mg/mL in DMSO
• Storage: -20°C
• IUPAC Name: (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-[(2S)-butan-2-yl]-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-tetramethylspiro[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/C48H74O14/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/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/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
• InChIKey: AZSNMRSAGSSBNP-XPNPUAGNSA-N
• SMILES: CCC(C)C1C(CCC2(O1)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)C

Ivermectin (CAS 70288-86-7) is a medication that is effective against many types of parasites. It is used to treat head lice, scabies, river blindness, strongyloidiasis, and lymphatic filariasis, among others. Ivermectin and other avermectins (insecticides most frequently used in home-use ant baits) are macrocyclic lactones derived from the bacterium Streptomyces avermitilis. Ivermectin kills by interfering with nervous system and muscle function, in particular by enhancing inhibitory neurotransmission. Ivermectin is a mixture of mostly avermectin H2B1a (CAS 71827-03-7) with some avermectin H2B1b (CAS 70209-81-3), which are macrolides from STREPTOMYCES avermitilis. Ivermectin may exerts its antiviral effect, including its potential activity against severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2), by binding to the importin (IMP) alpha/beta1 heterodimer, which is responsible for the nuclear import of viral proteins such as the integrase (IN) protein. This inhibits nuclear import of host and viral proteins and may inhibit viral replication.

Reference

1: Peachey LE, Pinchbeck GL, Matthews JB, Burden FA, Lespine A, von Samson-Himmelstjerna G, Krücken J, Hodgkinson JE. P-glycoproteins play a role in ivermectin resistance in cyathostomins. Int J Parasitol Drugs Drug Resist. 2017 Oct 25;7(3):388-398. doi: 10.1016/j.ijpddr.2017.10.006. [Epub ahead of print] PubMed PMID: 29121562.
2: Richards FO Jr. Mass Administration of Ivermectin in Areas Where Loa loa Is Endemic. N Engl J Med. 2017 Nov 8. doi: 10.1056/NEJMe1712713. [Epub ahead of print] PubMed PMID: 29117480.
3: Heredia Cardenas R, Romero Núñez C, Miranda Contreras L. Efficacy of two anthelmintic treatments, spinosad/milbemycin oxime and ivermectin/praziquantel in dogs with natural Toxocara spp. infection. Vet Parasitol. 2017 Nov 30;247:77-79. doi: 10.1016/j.vetpar.2017.09.016. Epub 2017 Sep 22. PubMed PMID: 29080769.
4: Chen IS, Kubo Y. Ivermectin and its target molecules: shared and unique modulation mechanisms of ion channels and receptors by ivermectin. J Physiol. 2017 Oct 23. doi: 10.1113/JP275236. [Epub ahead of print] PubMed PMID: 29063617.
5: Moreira N, Sandini TM, Reis-Silva TM, Navas-Suáresz P, Auada AVV, Lebrun I, Flório JC, Bernardi MM, Spinosa HS. Ivermectin reduces motor coordination, serum testosterone, and central neurotransmitter levels but does not affect sexual motivation in male rats. Reprod Toxicol. 2017 Oct 18;74:195-203. doi: 10.1016/j.reprotox.2017.10.002. [Epub ahead of print] PubMed PMID: 29055807.
6: Walker M, Pion SDS, Fang H, Gardon J, Kamgno J, Basáñez MG, Boussinesq M. The macrofilaricidal efficacy of repeated doses of ivermectin for the treatment of river blindness. Clin Infect Dis. 2017 Jul 19. doi: 10.1093/cid/cix616. [Epub ahead of print] PubMed PMID: 29020189.
7: Echazú A, Juarez M, Vargas PA, Cajal SP, Cimino RO, Heredia V, Caropresi S, Paredes G, Arias LM, Abril M, Gold S, Lammie P, Krolewiecki AJ. Albendazole and ivermectin for the control of soil-transmitted helminths in an area with high prevalence of Strongyloides stercoralis and hookworm in northwestern Argentina: A community-based pragmatic study. PLoS Negl Trop Dis. 2017 Oct 9;11(10):e0006003. doi: 10.1371/journal.pntd.0006003. eCollection 2017 Oct. PubMed PMID: 28991899; PubMed Central PMCID: PMC5648268.
8: Khowawisetsut L, Sarasombath PT, Thammapalo S, Loymek S, Korbarsa T, Nochote H, Phuakrod A, Choochote W, Wongkamchai S. Therapeutic trial of doxycyclin plus ivermectin for the treatment of Brugia malayi naturally infected cats. Vet Parasitol. 2017 Oct 15;245:42-47. doi: 10.1016/j.vetpar.2017.08.009. Epub 2017 Aug 18. PubMed PMID: 28969836.
9: Fiel CA, Steffan PE, Muchiut SM, Fernández AS, Bernat G, Riva E, Lloberas MM, Almada A, Homer D. An attempt to replace an ivermectin-resistant Cooperia spp. population by a susceptible one on grazing pastures based on epidemiological principles and refugia management. Vet Parasitol. 2017 Nov 15;246:53-59. doi: 10.1016/j.vetpar.2017.08.026. Epub 2017 Sep 1. PubMed PMID: 28969781.
10: de Souza DK, Ahorlu CS, Adu-Amankwah S, Otchere J, Mensah SK, Larbi IA, Mensah GE, Biritwum NK, Boakye DA. Community-based trial of annual versus biannual single-dose ivermectin plus albendazole against Wuchereria bancrofti infection in human and mosquito populations: study protocol for a cluster randomised controlled trial. Trials. 2017 Oct 2;18(1):448. doi: 10.1186/s13063-017-2196-9. PubMed PMID: 28969715; PubMed Central PMCID: PMC5625710.