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Monensin sodium salt

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Monensin sodium salt Basic information

Product Name:
Monensin sodium salt
Synonyms:
  • Coban45
  • gamma,2,8-tetramethyl--furyl)-2-furyl)-9-hydroxy-beta-methoxy-alphmonosod
  • methyl-5-(tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2h-pyran-2-yl)-2
  • monensin,monosodiumsalt
  • Monensin,monosodiumsalt(9CI)
  • Previouscas:22136-43-2
  • Sodiummonensin
  • 2-[5-Ethyltetrahydro-5-[tetrahydro-3-Methyl-5-[tetrahydro-6-hydroxy-6-(hydroxyMethyl)-3,5-diMethyl-2H-pyran-2-yl]-2-furyl]-2-furyl]-9-hydroxy-β-Methoxy-α,γ,2,8-tetraMethyl-
CAS:
22373-78-0
MF:
C36H63NaO12
MW:
710.87
EINECS:
244-941-7
Product Categories:
  • Inhibitors
  • Organics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • 22373-78-0
Mol File:
22373-78-0.mol
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Monensin sodium salt Chemical Properties

Melting point:
267-269 C
alpha 
57.3 º (c=4.0, in MeOH)
storage temp. 
2-8°C
solubility 
Soluble in methanol at 50mg/ml
form 
Off-white to beige solid
color 
White
BRN 
4122200
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey
XOIQMTLWECTKJL-BEMBKCOJSA-M
LogP
3.716 (est)
EPA Substance Registry System
Monensin, monosodium salt (22373-78-0)
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Safety Information

Hazard Codes 
T,T+
Risk Statements 
25-26/27/28
Safety Statements 
36/37/39-45-22
RIDADR 
UN 3462 6.1/PG 2
WGK Germany 
3
RTECS 
JH2830000
HazardClass 
6.1(a)
PackingGroup 
II
HS Code 
29419090

MSDS

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Monensin sodium salt Usage And Synthesis

Description

Monensin is a naturally occuring ionophorous antibiotic that preferentially forms complexes with monovalent cations to enable transport across lipid membranes. Through its ability to affect pH and the sodium-potassium balance of a cell, monensin can induce cell death in Gram-positive bacteria such as Micrococcus, Bacillus, and Staphylococcus (MICs = 1-12.5 μg/ml), reduce proliferation of P. falciparum and Coccicdium protozoa, and also prevent replication of certain viruses.

Chemical Properties

LIGHT CREAM AMORPHOUS POWDER

Uses

Poliether antibiotic. Coccidiostat.

Uses

antifungal

Uses

antibacterial

Uses

Monensin sodium salt is used in potentiometric and spectroscopic studies of alkali metal ion complexes. Monensin (Na) is a polyether small molecule ionophore, capable of forming stable complexes to monovalent cations with specific affinity for Na+. Monensin presents a highly lipophilic scaffold around the bound ion, allowing movement of the complex through the lipid bilayer and consequent transport of the ion out of the cell. Excessive flux of ions out of the cell produces a cytotoxic effect and generates the antibiotic properties of Monensin.

General Description

Monensin is a polyether ionophoric antibiotic, which is produced by Streptomyces cinnamonensis. It is used to treat bacterial, fungal and parasitic infections. Monensin prevents the growth of colon cancer cells. It facilitates the transport of sodium and potassium ions between intracellular and extracellular spaces. Monensin prevents coccidiosis?in poultry production.

Biochem/physiol Actions

Na+ ionophore; blocks glycoprotein secretion; may induce catecholamine secretion from chromaffin cells. Useful in potentiometric and spectroscopic studies of alkali metal ion complexes.

storage

-20°C

Purification Methods

Crystallise it from EtOH/H2O [Cox et al. J Am Chem Soc 107 4297 1985].

References

[1] DANIEL AOWICKI  Adam H. Structure and antimicrobial properties of monensin A and its derivatives: summary of the achievements.[J]. BioMed Research International, 2013: 742149. DOI:10.1155/2013/742149
[2] KARL-JOSEF KALLEN  David A  Paul Quinn. Monensin inhibits synthesis of plasma membrane sphingomyelin by blocking transport of ceramide through the Golgi: Evidence for two sites of sphingomyelin synthesis in BHK cells[J]. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1993, 1166 2: Pages 305-308. DOI:10.1016/0005-2760(93)90111-l
[3] W F BOSS  H H M  D J Morré. Monensin-induced swelling of Golgi apparatus cisternae mediated by a proton gradient.[J]. European journal of cell biology, 1984, 34 1: 1-8.
[4] HILTON H. MOLLENHAUER  Loyd D R  D James Morré. Alteration of intracellular traffic by monensin; mechanism, specificity and relationship to toxicity[J]. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 1990, 1031 2: Pages 225-246. DOI:10.1016/0304-4157(90)90008-z
[5] SUSANNE HAFNER S J L Michael Schmiech. The Cardenolide Glycoside Acovenoside A Interferes with Epidermal Growth Factor Receptor Trafficking in Non-Small Cell Lung Cancer Cells.[J]. ACS Applied Energy Materials, 2021: 611657. DOI:10.3389/fphar.2021.611657
[6] KENTARO OH-HASHI. Comparative Analysis of CREB3 and CREB3L2 Protein Expression in HEK293 Cells.[J]. International Journal of Molecular Sciences, 2021, 22 5. DOI:10.3390/ijms22052767

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