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+].CC[C@]1(CC[C@@H](O1)[C@@]2(C)CC[C@]3(C[C@H](O)[C@@H](C)[C@H](O3)[C@H](C)[C@H](OC)[C@@H](C)C([O-])=O)O2)[C@H]4O[C@@H](C[C@H]4C)[C@H]5O[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

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C36H61O11
Molecular Weight	669.8629
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	17 / 17
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8583	COBAN Approved Use For the prevention of coccidiosis. Launch Date 1987

PubMed

Title	Date	PubMed
Rapid internalization and recycling of the human neuropeptide Y Y(1) receptor.	2002-02-22	11741903
Constitutive internalization of constitutively active agiotensin II AT(1A) receptor mutants is blocked by inverse agonists.	2002-02-22	11729186
Organization of cyclic AMP-dependent connexin 43 in Swiss 3T3 cells attached to a cellulose substratum.	2002-01	11761161
Detection of two distinct transporter systems for 2-deoxyglucose uptake by the opportunistic pathogen Pneumocystis carinii.	2001-12-01	11718673
Engineering of complex polyketide biosynthesis--insights from sequencing of the monensin biosynthetic gene cluster.	2001-12	11774001
Acidic vesicles of Schistosoma mansoni.	2001-12	11763428
Evidence that release of adenosine triphosphate from endothelial cells during increased shear stress is vesicular.	2001-12	11707694
Regulation of Ca(2+) signals in a parotid cell line Par-C5.	2001-12	11684033
Efficient and sensitive screening and confirmation of residues of selected polyether ionophore antibiotics in liver and eggs by liquid chromatography-electrospray tandem mass spectrometry.	2001-11	11763080
Rhabdomyolysis, acute renal failure, and death after monensin ingestion.	2001-11	11684567
NAD degradation and regulation of CD38 expression by human monocytes/macrophages.	2001-11	11683883
The importance of Na+/H+ exchanger for the generation of procoagulant activity by porcine blood platelets.	2001-11	11674862
Conjugation of anti-My9 antibody to stealth monensin liposomes and the effect of conjugated liposomes on the cytotoxicity of immunotoxin.	2001-10-19	11578743
Prion protein protects human neurons against Bax-mediated apoptosis.	2001-10-19	11522774
Long-lasting aberrant tubulovesicular membrane inclusions accumulate in developing motoneurons after a sublethal excitotoxic insult: a possible model for neuronal pathology in neurodegenerative disease.	2001-10-15	11588180
Hydrogen peroxide activates Na(+)-dependent Ca(2+) influx in coronary endothelial cells.	2001-10-12	11587541
Secretion of gelatinases and activation of gelatinase A (MMP-2) by human rheumatoid synovial fibroblasts.	2001-10	11727833
Characteristics of the hepatic stellate cell-selective carrier mannose 6-phosphate modified albumin (M6P(28)-HSA).	2001-10	11589768
Biologically active APRIL is secreted following intracellular processing in the Golgi apparatus by furin convertase.	2001-10	11571266
Gap junction assembly: PTX-sensitive G proteins regulate the distribution of connexin43 within cells.	2001-10	11546658
Effects of monensin and forage:concentrate ratio on feed intake, endocrine, and ovarian function in beef heifers.	2001-09-15	11530263
Hyaluronan enters keratinocytes by a novel endocytic route for catabolism.	2001-09-14	11451952
A novel function of phosphorothioate oligodeoxynucleotides as chemoattractants for primary macrophages.	2001-09-01	11509631
Spatio-temporal expression of a gene encoding a putative RNA-binding protein during the early larval development of the mollusc Patella vulgata.	2001-09	11685576
Fatal rhabdomyolysis after acute sodium monensin (Rumensin) toxicity: case report.	2001-09	11588643
Yolk granules are differentially acidified during embryo development in the stick insect Carausius morosus.	2001-09	11572096
Regulation of epidermal growth factor receptor endocytosis by wortmannin through activation of Rab5 rather than inhibition of phosphatidylinositol 3-kinase.	2001-09	11559593
Expression of P-glycoprotein in the chicken.	2001-09	11544075
Budesonide reduces vascular endothelial growth factor secretion and expression in airway (Calu-1) and alveolar (A549) epithelial cells.	2001-08-10	11502275
Bradykinin increases Na(+)-K(+) pump activity in cultured guinea-pig tracheal smooth muscle cells.	2001-08	11498520
The effects of insulin, glucose, and pyruvate on the kinetics of leptin secretion.	2001-08	11459803
Matrix vesicles and media vesicles as nonclassical pathways for the secretion of m-Calpain from MC3T3-E1 cells.	2001-07-20	11453670
Generation of ceramide in murine macrophages infected with Leishmania donovani alters macrophage signaling events and aids intracellular parasitic survival.	2001-07	11681721
Azithromycin, a lysosomotropic antibiotic, impairs fluid-phase pinocytosis in cultured fibroblasts.	2001-07	11499789
Effect of monensin on the performance and nitrogen utilization of lactating dairy cows consuming fresh forage.	2001-07	11467822
Flow cytometric measurement of intracellular Th1 and Th2 cytokine production by human villous and extravillous cytotrophoblast.	2001-07	11440543
Stealth monensin immunoliposomes as potentiator of immunotoxins in vitro.	2001-07	11438419
Signaling pathways initiated in macrophages after engagement of type A scavenger receptors.	2001-07	11435497
LC/MS confirmation of ionophores in animal feeds.	2001-06-22	11417625
The interaction between wheat germ agglutinin and other plant lectins with prostate cancer cells Du-145.	2001-06-19	11397565
Evaluation of monensin and brefeldin A for flow cytometric determination of interleukin-1 beta, interleukin-6, and tumor necrosis factor-alpha in monocytes.	2001-06-15	11449408
Studies on chemical modification of monensin IX. Synthesis of 26-substituted monensins and their Na+ ion transport activity.	2001-06	11411522
Increased frequency of interleukin 4 producing CD4+ and CD8+ cells in peripheral blood from patients with systemic sclerosis.	2001-06	11409116
Stimulated cord blood lymphocytes have a low percentage of Th1 and Th2 cytokine secreting T cells although their activation is similar to adult controls.	2001-05-01	11400701
Expression and function of P-glycoprotein and absence of multidrug resistance-related protein in rat and beige mouse peritoneal mast cells.	2001-05	11563538
Increasing the intra-Golgi pH of cultured LS174T goblet-differentiated cells mimics the decreased mucin sulfation and increased Thomsen-Friedenreich antigen (Gal beta1-3GalNac alpha-) expression seen in colon cancer.	2001-05	11425799
Colocalization of beta 1,4galactosyltransferase with mannose 6-phosphate receptor in monensin-induced TGN-derived structures.	2001-02	11444150
HIV infection and aging: enhanced Interferon- and Tumor Necrosis Factor-alpha production by the CD8+ CD28- T subset.	2001	11696237
Role of CD28/B7 costimulation and IL-12/IL-10 interaction in the radiation-induced immune changes.	2001	11532194
Molecular and cellular mechanisms of adipose secretion: comparison of leptin and angiotensinogen.	2001	11500944

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:19:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:19:17 GMT 2025`
Record UNII	1GS872GAFV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-343257

Preferred Name

English

MONENSIN SODIUM

Common Name

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