I8898

Sigma-Aldrich

Ivermectin

Synonym(s):
MK-933, 22,23-Dihydroavermectin B1
CAS Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

form

powder

solubility

MEK: 50 mg/mL

Featured Industry

Agriculture
Environmental

Mode of action

cell membrane | interferes

antibiotic activity spectrum

parasites

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

2-8°C

SMILES string

[H][C@@]1(O[C@]2(CC[C@@H]1C)C[C@@H]3C[C@@H](C\C=C(C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C6/CO[C@]7([H])[C@H](O)C(C)=C[C@@H](C(=O)O3)[C@]67O)O2)[C@@H](C)CC

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

InChI key

AZSNMRSAGSSBNP-XPNPUAGNSA-N

Gene Information

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Related Categories

General description

Ivermectin is a macro-cyclic lactone, derived from avermectin. It functions as an antiparasitic agent. Ivermectin is used against gastrointestinal roundworms, lungworms, mites and lice. It is used to treat onchocerciasis, strongyloidiasis, ascariasis and filariases.

Application

Ivermectin has been used:
  • in Caenorhabditis elegans fecundity assay
  • in larval development test
  • to measure in vivo topical acaricide activity of compounds in rats
  • to assess its acute and chronic effects to zebrafish
  • in percutaneous drug injection method to treat cystic echinococcosis
  • in liquid chromatography with fluorescence detection method

Packaging

250 mg in poly bottle
1 g in poly bottle

Biochem/physiol Actions

Positive allosteric modulator of α7 neuronal nicotinic acetylcholine receptor; also modulates glutamate-GABA-activated chloride channels.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Other Notes

Primarily ivermectin B1a.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

  1. What is the solution stability of Ivermectin (Product No. I8898)?

    Stock solutions of Ivermectin in DMSO at a concentration of 10 mM have been found to be stable for 2 weeks at -20°C, according to Shan, Q., et al., in Ivermectin, an Unconventional Agonist of the Glycine Receptor Chloride Channel.  J. Biol. Chem., 276(16), 12556-12564 (2001).

  2. What is the composition of the submoieties B1A and B1B in Product No. I8898, Ivermectin?

    Unfortunately we do not test each lot to determine the composition.  In the past, lots have been ~95% B1A and ~5% B1B; however there will be lot-to-lot variation.

  3. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Simultaneous determination of emamectin and ivermectin residues in Atlantic salmon muscle by liquid chromatography with fluorescence detection
Riet JM, et al.
Journal of AOAC (Association of Official Analytical Chemists) International, 84(5), 1358-1362 (2001)
Hidden in plain sight-multiple resistant species within a strongyle community
McIntyre J, et al.
Veterinary Parasitology (2018)
An in vivo rodent model for identifying and characterizing acaricides
Gutierrez JA, et al.
Journal of Medical Entomology, 43(3), 526-532 (2006)
Effects of ivermectin on Danio rerio: a multiple endpoint approach: behaviour, weight and subcellular markers
Domingues I, et al.
Ecotoxicology (London, England), 25(3), 491-499 (2016)
R M Krause et al.
Molecular pharmacology, 53(2), 283-294 (1998-03-14)
We report that preapplication of ivermectin, in the micromolar range, strongly enhances the subsequent acetylcholine-evoked current of the neuronal chick or human alpha7 nicotinic acetylcholine receptors reconstituted in Xenopus laevis oocytes and K-28 cells. This potentiation does not result from...

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