Monensin

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 Search

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

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
In vitro activity of the polyether ionophorous antibiotic monensin against the cyst form of Toxoplasma gondii.	2000 Oct	11072898
HIV infection and aging: enhanced Interferon- and Tumor Necrosis Factor-alpha production by the CD8+ CD28- T subset.	2001	11696237
Synthesis of monensin derivatives and their effect on the activity of ricin A-chain immunotoxins.	2001	11217376
Effect of ionophores on in vitro excystment of Paragonimus ohirai metacercariae.	2001 Apr	11355686
Effects of L-glutamate, D-aspartate, and monensin on glycolytic and oxidative glucose metabolism in mouse astrocyte cultures: further evidence that glutamate uptake is metabolically driven by oxidative metabolism.	2001 Apr	11222924
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
Regulation of Ca(2+) signals in a parotid cell line Par-C5.	2001 Dec	11684033
Colocalization of beta 1,4galactosyltransferase with mannose 6-phosphate receptor in monensin-induced TGN-derived structures.	2001 Feb	11444150
Cloned neuropeptide Y (NPY) Y1 and pancreatic polypeptide Y4 receptors expressed in Chinese hamster ovary cells show considerable agonist-driven internalization, in contrast to the NPY Y2 receptor.	2001 Feb	11179953
Regulation of the catalytic activity of preexisting tyrosinase in black and Caucasian human melanocyte cell cultures.	2001 Jan 15	11139343
Matrix vesicles and media vesicles as nonclassical pathways for the secretion of m-Calpain from MC3T3-E1 cells.	2001 Jul 20	11453670
Regulation by retinoic acid of acylation-stimulating protein and complement C3 in human adipocytes.	2001 Jun 1	11368771
Evaluation of monensin and brefeldin A for flow cytometric determination of interleukin-1 beta, interleukin-6, and tumor necrosis factor-alpha in monocytes.	2001 Jun 15	11449408
Measurement of potency and lipids in monensin fermentation broth by near-infrared spectroscopy.	2001 May	11275433
Evaluation of canarypox-induced CD8(+) responses following immunization by measuring the effector population IFNgamma production.	2001 May 1	11348664
Expression of P-glycoprotein in the chicken.	2001 Sep	11544075
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

Official Name

English

2-(5-ETHYLTETRAHYDRO-5-(TETRAHYDRO-3-METHYL-5-(TETRAHYDRO-6-HYDROXY-6-(HYDROXYMETHYL)-3,5-DIMETHYL-2H-PYRAN-2-YL)-2-FURYL)-2-FURYL)-9-HYDROXY-.BETA.-METHOXY-.ALPHA.,.GAMMA.,2,8-TETRAMETHYL-1,6-DIOXASPIRO(4.5)DECANE-7-BUTYRIC ACID

Systematic Name

English

MONENSIN [GREEN BOOK]

Common Name

English

MONENSIN [USP IMPURITY]

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

Common Name

English

MONENSIN [MI]

Common Name

English

monensin [INN]

Common Name

English

MONENSIN [USAN]

Common Name

English

MONENSIN [MART.]

Common Name

English

A-3823A

Code

English

MONENSIN [USP MONOGRAPH]

Common Name

English

MONENSIN [HSDB]

Common Name

English

4-(2-(2-ETHYL-3'-METHYL-5'-(TETRAHYDRO-6-HYDROXY-6-HYDROXYMETHYL-3,5-DIMETHYLPYRAN-2-YL)PERHYDRO-2,2'-BIFURAN-5-YL)-9-HYDROXY-2,8-DIMETHYL-1,6-DIOXASPIRO(4.5)DEC-7-YL)3-METHOXY-2-METHYLPENTANOIC ACID

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277