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Key Documents

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I8898

Sigma-Aldrich

Ivermectin

Sinónimos:

22,23-Dihydroavermectin B1, MK-933

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About This Item

Número de CAS:
70288-86-7
MDL number:
MFCD00869511
UNSPSC Code:
12352200
PubChem Substance ID:
24278497
NACRES:
NA.77

form

powder

solubility

MEK: 50 mg/mL

antibiotic activity spectrum

parasites

application(s)

agriculture
environmental

mode of action

cell membrane | interferes

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

human ... ABCB1(5243) , CYP3A4(1576)
mouse ... Abcb1a(18671) , Abcb1b(18669)

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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

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 featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
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.

Other Notes

Primarily ivermectin B1a.

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
Ivermectin in human medicine
Ottesen EA and Campbell W
The Journal of Antimicrobial Chemotherapy, 34(2), 195-203 (1994)
R J Martin et al.
International journal for parasitology, 28(6), 849-862 (1998-07-23)
Two of three major types of anthelminitic, the avermectins and the nicotinic agonists, exert their therapeutic effect by an action on ligand-gated membrane ion-channels of nematodes. The avermectins, such as ivermectin, open glutamategated chloride channels which have so far been
Ivermectin used in percutaneous drug injection method for the treatment of liver hydatid disease in sheep
Hokelek M, et al.
Gastroenterology, 122(4), 957-962 (2002)
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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