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I8898

Sigma-Aldrich

Ivermectin

Synonym(s):

22,23-Dihydroavermectin B1, MK-933

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250 MG
556,00 kr
1 G
1 660,00 kr

556,00 kr

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250 MG
556,00 kr
1 G
1 660,00 kr

About This Item

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

556,00 kr

In StockDetails

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form

powder

Quality Level

100

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,[1] derived from avermectin.[2] 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.[2]

Application

Ivermectin has been used:
  • in Caenorhabditis elegans fecundity assay[3]
  • in larval development test[4]
  • to measure in vivo topical acaricide activity of compounds in rats[5]
  • to assess its acute and chronic effects to zebrafish[6]
  • in percutaneous drug injection method to treat cystic echinococcosis[7]
  • in liquid chromatography with fluorescence detection method[8]

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.

Signal Word

Danger

Hazard Statements

H300,H311,H351,H360D,H410

Hazard Classifications

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV0451
MKCM8215
MKCM4277
MKCK0618
MKCC9996

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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)
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)
Ivermectin in human medicine
Ottesen EA and Campbell W
The Journal of Antimicrobial Chemotherapy, 34(2), 195-203 (1994)
An in vivo rodent model for identifying and characterizing acaricides
Gutierrez JA, et al.
Journal of Medical Entomology, 43(3), 526-532 (2006)
View All Related Papers

Questions

1–6 of 6 Questions  

  1. Is product I8898, Ivermectin the analytical standard grade level? if not, what level is it?

    1 answer

    1. This product is considered a research grade with an assigned quality level of 100. Other Ivermectin products available are primary or secondary pharmaceutical reference standards. Please see the link below to review additional information regarding product quality levels:
      https://www.sigmaaldrich.com/life-science/quality-and-regulatory-management/m-clarity-program

      Please see the following link to review alternative Ivermectin standard product options:
      https://www.sigmaaldrich.com/search/ivermectin-standard?focus=products&page=1&perpage=30&sort=relevance&term=ivermectin%20standard&type=product

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  2. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

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

    1 answer

    1. 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.

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

    1 answer

    1. 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).

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  5. How does the storage temperature relate to shipping conditions?

    1 answer

    1. The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.

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  6. What is the molecular weight of Product No. I8898, Ivermectin?

    1 answer

    1. This product is a mixture of two submoieties B1A, MW 891.1 and B1B, MW 877.1. It is typically predominantly B1A, so you may use a molecular weight of 890 in your calculations.

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