Monensin

Source: Wikipedia, the free encyclopedia.
Monensin A
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
ECHA InfoCard
 100.037.398 Edit this at Wikidata
E number E714 (antibiotics)
KEGG
UNII
  • InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1 checkY
    Key: GAOZTHIDHYLHMS-KEOBGNEYSA-N checkY
  • InChI=1/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1
    Key: GAOZTHIDHYLHMS-KEOBGNEYBF
  • O=C(O)[C@@H](C)[C@H](OC)[C@H](C)[C@H]5O[C@]1(O[C@@](C)(CC1)[C@@H]2O[C@@](CC)(CC2)[C@@H]4O[C@@H]([C@H]3O[C@@](O)(CO)[C@@H](C[C@@H]3C)C)C[C@@H]4C)C[C@H](O)[C@H]5C
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
QP51BB03 (WHO
)
Legal status
Related compounds
Related
ionophores
Related compounds
 Monensin A methyl ester,
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Monensin is a

Streptomyces 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 first total synthesis of monensin was reported in 1979 by Kishi et al.[4]

Mechanism of action

The structure of the sodium (Na+) complex of monensin A.

Monensin A is an

antibacterial properties of monensin and its derivatives are a result of their ability to transport metal cations through cellular and subcellular membranes.[9]

Uses

Monensin is used extensively in the beef and dairy industries to prevent coccidiosis, increase the production of propionic acid and prevent bloat.[10] Furthermore, monensin, but also its derivatives monensin methyl ester (MME), and particularly monensin decyl ester (MDE) are widely used in ion-selective electrodes.[11][12][13] In laboratory research, monensin is used extensively to block Golgi transport.[14][15][16]

Toxicity

Monensin has some degree of activity on mammalian cells and thus toxicity is common. This is especially pronounced in horses, where monensin has a median lethal dose 1/100th that of ruminants. Accidental poisoning of equines with monensin is a well-documented occurrence which has resulted in deaths.[17]

References

  1. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  2. ^
    PMID 23509771
    .
  3. PMID 12692092
    .
  4. ISBN 3-527-29284-5
    .
  5. doi:10.1016/j.molstruc.2006.07.046
    .
  6. PMID 5453344
    .
  7. PMID 22564680
    .
  8. PMID 2160275
    .
  9. PMID 18375122
    .
  10. doi:10.1016/S0737-0806(96)80059-1
    .
  11. doi:10.2116/analsci.6.227
    .
  12. PMID 15797327
    .
  13. doi:10.1016/S0925-4005(99)00508-0
    .
  14. PMID 6682112
    .
  15. PMID 8443249
    .
  16. PMID 8980903
    .
  17. ^ "Tainted feed blamed for 4 horse deaths at Florida stable". Associated Press. 2014-12-16.
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