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Details

Stereochemistry ABSOLUTE
Molecular Formula C36H62O11
Molecular Weight 670.8709
Optical Activity UNSPECIFIED
Defined Stereocenters 17 / 17
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Monensin

SMILES

[H][C@@]1(C[C@H](C)[C@@]([H])(O1)[C@]2(CC)CC[C@@]([H])(O2)[C@]3(C)CC[C@]4(C[C@H](O)[C@@H](C)[C@]([H])(O4)[C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O3)[C@@]5([H])O[C@@](O)(CO)[C@H](C)C[C@@H]5C

InChI

InChIKey=GAOZTHIDHYLHMS-KEOBGNEYSA-N
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

HIDE SMILES / InChI

Molecular Formula C36H62O11
Molecular Weight 670.8709
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 17 / 17
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Monensin is an antibiotic produced as a byproduct of fermentation by Streptomyces cinnamonensis and belongs to a family of drugs known as polyether antibiotics or ionophores. The drug was approved by FDA for the prevention of coccidiosis in turkeys, chickens, quail, cattle, goats, calves (Coban, Rumensin). The exact mechanism of monesin action is unknown, however there are several hypotesis, which includes the inhibition of K+ transport, the inhibition of the transport of carbohydrates across the host cell membrane, the interruption host cell invasion by sporozoites, etc.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
COBAN

PubMed

Sample Use Guides

In Vivo Use Guide
Monensin is taken orally at a dose of 73 g/ton feed (quail), 54-90 g/ton feed (turkeys), 90-110 g/ton feed (chickens), 0.14-0.42 mg/pound body weight (cattle fed in confinement for slaughter, growing cattle, mature reproducing beef cows), 0.14-1 mg/pound body weight (calves), 20 g/ton feed (goats).
Route of Administration: Oral
In Vitro Use Guide
Eimeria tenella (Coccidia, Sporozoa) was incubated in media containing 1 ppm, 10 ppm or 100 ppm of monesin and free merozoites were destroyed after 20 min. Dose of 125 ppm monensin was found to bring about an equivalent protective effect against an infection with 40,000 Eimeria tenella oocysts.
Substance Class Chemical
Record UNII
906O0YJ6ZP
Record Status Validated (UNII)
Record Version