MONENSIN SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H61O11.Na
Molecular Weight	692.8527
Optical Activity	UNSPECIFIED
Defined Stereocenters	17 / 17
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[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=XOIQMTLWECTKJL-PDHYURILSA-M

InChI=1S/C36H62O11.Na/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);/q;+1/p-1/t19-,20+,21+,22+,23+,24+,25-,26-,27+,28-,29-,30-,31-,33+,34-,35+,36-;/m0./s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20709963

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

Condition	Modality	Targets	Highest Phase	Product
Coccidiosis 45 Sources: https://www.elanco.us/products-services/poultry/coban	Preventing		Approved 8429	COBAN Approved Use For the prevention of coccidiosis. Launch Date 1987

PubMed

Title	Date	PubMed
Assessment of drugs against Cryptosporidium parvum using a simple in vitro screening method.	1999 Sep 15	10499272
Molecular and cellular mechanisms of adipose secretion: comparison of leptin and angiotensinogen.	2001	11500944
Interaction between monensin and CCl4 after chronic treatment: dolichol and retinol content of rat liver sinusoidal cells.	2001	11392063
Intracellular calibration of the fluorescent Mg2+ indicator furaptra in rat ventricular myocytes.	2001 Apr	11374066
The effect of season and monensin sodium on the digestive characteristics of autumn and spring pasture fed to sheep.	2001 Apr	11325179
Intracellular pH regulation by Mycobacterium smegmatis and Mycobacterium bovis BCG.	2001 Apr	11283297
Cytotoxic mechanism of the ribotoxin alpha-sarcin. Induction of cell death via apoptosis.	2001 Apr	11277935
Budesonide reduces vascular endothelial growth factor secretion and expression in airway (Calu-1) and alveolar (A549) epithelial cells.	2001 Aug 10	11502275
Engineering of complex polyketide biosynthesis--insights from sequencing of the monensin biosynthetic gene cluster.	2001 Dec	11774001
Evidence that release of adenosine triphosphate from endothelial cells during increased shear stress is vesicular.	2001 Dec	11707694
The effects of particulate wear debris, cytokines, and growth factors on the functions of MG-63 osteoblasts.	2001 Feb	11216681
Impairment of bile salt-dependent lipase secretion in AR4-2J rat pancreatic cells induces its degradation by the proteasome.	2001 Feb 26	11239821
Group IIA and group V secretory phospholipase A(2): quantitative analysis of expression and secretion and determination of the localization and routing in rat mesangial cells.	2001 Jan 15	11341961
Potent and specific antitumor effects of an anti-CD22-targeted cytotoxic ribonuclease: potential for the treatment of non-Hodgkin lymphoma.	2001 Jan 15	11154233
Regulation of the catalytic activity of preexisting tyrosinase in black and Caucasian human melanocyte cell cultures.	2001 Jan 15	11139343
Generation of ceramide in murine macrophages infected with Leishmania donovani alters macrophage signaling events and aids intracellular parasitic survival.	2001 Jul	11681721
Azithromycin, a lysosomotropic antibiotic, impairs fluid-phase pinocytosis in cultured fibroblasts.	2001 Jul	11499789
Flow cytometric measurement of intracellular Th1 and Th2 cytokine production by human villous and extravillous cytotrophoblast.	2001 Jul	11440543
Stealth monensin immunoliposomes as potentiator of immunotoxins in vitro.	2001 Jul	11438419
Signaling pathways initiated in macrophages after engagement of type A scavenger receptors.	2001 Jul	11435497
The interaction between wheat germ agglutinin and other plant lectins with prostate cancer cells Du-145.	2001 Jun 19	11397565
Expression and function of P-glycoprotein and absence of multidrug resistance-related protein in rat and beige mouse peritoneal mast cells.	2001 May	11563538
Inhibition of Na+,K+-ATPase by interferon gamma down-regulates intestinal epithelial transport and barrier function.	2001 May	11313309
Measurement of potency and lipids in monensin fermentation broth by near-infrared spectroscopy.	2001 May	11275433
Stimulated cord blood lymphocytes have a low percentage of Th1 and Th2 cytokine secreting T cells although their activation is similar to adult controls.	2001 May 1	11400701
NAD degradation and regulation of CD38 expression by human monocytes/macrophages.	2001 Nov	11683883
Secretion of gelatinases and activation of gelatinase A (MMP-2) by human rheumatoid synovial fibroblasts.	2001 Oct	11727833
Characteristics of the hepatic stellate cell-selective carrier mannose 6-phosphate modified albumin (M6P(28)-HSA).	2001 Oct	11589768
Biologically active APRIL is secreted following intracellular processing in the Golgi apparatus by furin convertase.	2001 Oct	11571266
Conjugation of anti-My9 antibody to stealth monensin liposomes and the effect of conjugated liposomes on the cytotoxicity of immunotoxin.	2001 Oct 19	11578743
Prion protein protects human neurons against Bax-mediated apoptosis.	2001 Oct 19	11522774
Yolk granules are differentially acidified during embryo development in the stick insect Carausius morosus.	2001 Sep	11572096
Regulation of epidermal growth factor receptor endocytosis by wortmannin through activation of Rab5 rather than inhibition of phosphatidylinositol 3-kinase.	2001 Sep	11559593
Expression of P-glycoprotein in the chicken.	2001 Sep	11544075
Hyaluronan enters keratinocytes by a novel endocytic route for catabolism.	2001 Sep 14	11451952
Constitutive internalization of constitutively active agiotensin II AT(1A) receptor mutants is blocked by inverse agonists.	2002 Feb 22	11729186

Patents

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.

Name

Type

Language

MONENSIN SODIUM

Common Name

English

NSC-343257

Code

English

2-(2-ETHYLOCTAHYDRO-3'-METHYL-5'-(TETRAHYDRO-6-HYDROXY-6-(HYDROXYMETHYL)-3,5-DIMETHYL-2H-PYRAN-2-YL)(2,2'-BIFURAN-5-YL))-9-HYDROXY-.BETA.-METHOXY-.ALPHA.,.GAMMA.,2,8-TETRAMETHYL-1,6-DIOXASPIRO(4.5)DECAN-7-BUTANOIC ACID SODIUM SALT

Common Name

English

MONENSIN SODIUM [GREEN BOOK]

Common Name

English

MONENSIN SODIUM [USP IMPURITY]

Common Name

English

SODIUM MONENSIN

Common Name

English

MONENSIN SODIUM [USP MONOGRAPH]

Common Name

English

MONENSIN SODIUM [USP-RS]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277