U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of MONENSIN SODIUM

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

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
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

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

Eli Lilly|Indiana University School of Medicine
2
Curator's Comment: # Eli Lilly and the Department of Biochemistry of Indiana University School of Medicine

Approval Year

2011
587
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
COBAN

Approved Use

For the prevention of coccidiosis.

Launch Date

1987
PubMed

PubMed

TitleDatePubMed
Assessment of drugs against Cryptosporidium parvum using a simple in vitro screening method.
1999 Sep 15
Molecular and cellular mechanisms of adipose secretion: comparison of leptin and angiotensinogen.
2001
Intracellular calibration of the fluorescent Mg2+ indicator furaptra in rat ventricular myocytes.
2001 Apr
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
Regulation of the catalytic activity of preexisting tyrosinase in black and Caucasian human melanocyte cell cultures.
2001 Jan 15
Generation of ceramide in murine macrophages infected with Leishmania donovani alters macrophage signaling events and aids intracellular parasitic survival.
2001 Jul
Azithromycin, a lysosomotropic antibiotic, impairs fluid-phase pinocytosis in cultured fibroblasts.
2001 Jul
Flow cytometric measurement of intracellular Th1 and Th2 cytokine production by human villous and extravillous cytotrophoblast.
2001 Jul
Stealth monensin immunoliposomes as potentiator of immunotoxins in vitro.
2001 Jul
Signaling pathways initiated in macrophages after engagement of type A scavenger receptors.
2001 Jul
Inhibition of Na+,K+-ATPase by interferon gamma down-regulates intestinal epithelial transport and barrier function.
2001 May
Characteristics of the hepatic stellate cell-selective carrier mannose 6-phosphate modified albumin (M6P(28)-HSA).
2001 Oct
Conjugation of anti-My9 antibody to stealth monensin liposomes and the effect of conjugated liposomes on the cytotoxicity of immunotoxin.
2001 Oct 19
Hyaluronan enters keratinocytes by a novel endocytic route for catabolism.
2001 Sep 14
Patents

Patents

06743440
2
JP2003527336A
18
JP2004231596A
2
JP2006034126A
2
JP2006052192A
2
JP2006520819A
15
JP2007236295A
2
JP2008230980A
4
JP2009108004A
2
JP2010530745A
4
JP2011506398A
20
JP3105919B2
2
JP3309356B2
2
JP4722360B2
18
JPH00539265A
2
JPH01152362A
2
JPH01218557A
2
JPH0193524A
2
JPH0291026A
6
JPH0327315A
5
JPH0347132A
4
JPH04208203A
2
JPH0539265A
2
JPH06184159A
4
JPH06298782A
2
JPH1143408A
10
JPS5513252A
6
JPS56167621A
2
JPS57177654A
2
JPS57209924A
2
JPS5724312A
4
JPS5984146A
2
JPS599550A
2
JPS5999246A
2
JPS62205086A
2
JPS63216821A
2

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 Fri Dec 15 16:06:41 GMT 2023
Edited
by admin
on Fri Dec 15 16:06:41 GMT 2023
Record UNII
1GS872GAFV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MONENSIN SODIUM
GREEN BOOK   MART.   USP   USP-RS  
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
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID2045573
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
FDA UNII
1GS872GAFV
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
PUBCHEM
23690927
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
RS_ITEM_NUM
1445481
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
CAS
22373-78-0
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL256105
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
NCI_THESAURUS
C82249
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
NSC
343257
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
244-941-7
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
SMS_ID
300000023789
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
DRUG BANK
DBSALT001710
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
Related Record Type Details
Structure of Monensin
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of Monensin
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966