 | |
| Names | |
|---|---|
| Preferred IUPAC name (2S,3R,4S)-4-[(2S,5R,7S,8R,9S)-2-{(2S,2′R,3′S,5R,5′R)-2-Ethyl-5′-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3′-methyl[2,2′-bioxolan]-5-yl}-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid | |
| Other names Monensic acid | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.037.398 |
| E number | E714(antibiotics) |
| KEGG |
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| UNII | |
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| Properties | |
| C36H62O11 | |
| Molar mass | 670.871 g/mol |
| Appearance | solid state, white crystals |
| Melting point | 104 °C (219 °F; 377 K) |
| 3x10−6 g/dm3 (20 °C) | |
| Solubility | ethanol,acetone,diethyl ether,benzene |
| Pharmacology | |
| QA16QA06 (WHO) QP51BB03 (WHO) | |
| Legal status | |
| Related compounds | |
Related | antibiotics,ionophores |
Related compounds | Monensin A methyl ester, |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Monensin is apolyetherantibiotic isolated fromStreptomyces cinnamonensis.[2] It is widely used in ruminant animal feeds.[2][3]
The structure of monensin was first described by Agtarap et al. in 1967, and was the first polyether antibiotic to have its structure elucidated in this way. The firsttotal synthesis of monensin was reported in 1979 byKishi et al.[4]
Monensin A is anionophore related to thecrown ethers with a preference to form complexes with monovalentcations such as: Li+, Na+, K+, Rb+, Ag+, and Tl+.[5][6] Monensin A is able to transport these cations across lipid membranes of cells in an electroneutral (i.e. non-depolarizing) exchange, playing an important role as an Na+/H+antiporter. Recent studies have shown that monensin may transport sodium ion through the membrane in both electrogenic and electroneutral manner.[7] This approach explains ionophoric ability and in consequence antibacterial properties of not only parental monensin, but also its derivatives that do not possess carboxylic groups. It blocksintracellular protein transport, and exhibitsantibiotic,antimalarial, and other biological activities.[8] Theantibacterial properties of monensin and its derivatives are a result of their ability to transport metal cations through cellular and subcellularmembranes.[9]
Monensin is used extensively in the beef and dairy industries to preventcoccidiosis, increase the production of propionic acid and prevent bloat.[10] Furthermore, monensin, but also its derivatives monensin methylester (MME), and particularly monensin decyl ester (MDE) are widely used inion-selective electrodes.[11][12][13] In laboratory research, monensin is used extensively to blockGolgi transport.[14][15][16]
Monensin has some degree of activity on mammalian cells and thus toxicity is common. This is especially pronounced in horses, where monensin has amedian lethal dose 1/100 that of ruminants. Accidental poisoning of equines with monensin is a well-documented occurrence which has resulted in deaths.[17][18]
