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.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Primarily ivermectin B1a.

Legal Information

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

Signal Word

Danger

hazcat

Acute Tox. 1 Oral - Acute Tox. 3 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Repr. 1B

storage_class_code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

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)
Ivermectin in human medicine
Ottesen EA and Campbell W
The Journal of Antimicrobial Chemotherapy, 34(2), 195-203 (1994)
Evaluation of the toxicity of 2-aminoimidazole antibiofilm agents using both cellular and model organism systems
Stowe SD, et al.
Drug and Chemical Toxicology, 35(3), 310-315 (2012)
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)

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