This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Monensin
DrugBank Accession Number
DB11430
Background

Monensin is a polyether isolated from Streptomyces cinnamonensis that presents antibiotic properties. It is widely used in ruminant animal feeds.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
Weight
Average: 670.881
Monoisotopic: 670.429212816
Chemical Formula
C36H62O11
Synonyms
  • Monensic acid
  • Monensin
  • Monensin A
  • Monensina
  • Monensinum
External IDs
  • A 3823A
  • A-3823A
  • ATCC 15413
  • Lilly 673140

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Monensin sodium1GS872GAFV22373-78-0XOIQMTLWECTKJL-PDHYURILSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Heterocyclic fatty acids
Alternative Parents
Methyl-branched fatty acids / Ketals / Hydroxy fatty acids / Oxanes / Tetrahydrofurans / Secondary alcohols / Hemiacetals / Oxacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers
show 5 more
Substituents
Acetal / Alcohol / Aliphatic heteropolycyclic compound / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Ether / Hemiacetal
show 15 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid, cyclic hemiketal, spiroketal, polyether antibiotic (CHEBI:27617) / Other Polyketides, Polyether antibiotics (C06693)
Affected organisms
Not Available

Chemical Identifiers

UNII
906O0YJ6ZP
CAS number
17090-79-8
InChI Key
GAOZTHIDHYLHMS-KEOBGNEYSA-N
InChI
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
IUPAC Name
(2S,3R,4S)-4-[(2S,5R,7S,8R,9S)-2-[(2S,2'R,3'S,5R,5'R)-2-ethyl-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid
SMILES
[H][C@@]1(C[C@H](C)[C@@]([H])(O1)[C@]1(CC)CC[C@@]([H])(O1)[C@]1(C)CC[C@]2(C[C@H](O)[C@@H](C)[C@]([H])(O2)[C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O1)[C@@]1([H])O[C@@](O)(CO)[C@H](C)C[C@@H]1C

References

General References
  1. Synge BA: Monensin poisoning in sheep. Vet Rec. 1989 Apr 15;124(15):410-1. [Article]
  2. Rumsey TS: Monensin in cattle: introduction. J Anim Sci. 1984 Jun;58(6):1461-4. [Article]
  3. Howell J, Hanson J, Onderka D, Harries WN: Monensin toxicity in chickens. Avian Dis. 1980 Oct-Dec;24(4):1050-3. [Article]
  4. Miller DJ: Monensin-tiamulin interaction. Vet Rec. 1981 Apr 4;108(14):317-8. [Article]
  5. Gerhards H, Fenner A, Schoon HA: [Monensin poisoning in horses]. Dtsch Tierarztl Wochenschr. 1986 Jul 23;93(7):323-6. [Article]
  6. Day LE, Chamberlin JW, Gordee EZ, Chen S, Gorman M, Hamill RL, Ness T, Weeks RE, Stroshane R: Biosynthesis of monensin. Antimicrob Agents Chemother. 1973 Oct;4(4):410-4. [Article]
  7. Biely J: Monensin in broiler rations. Avian Dis. 1973 Apr-Jun;17(2):362-8. [Article]
  8. Morley AJ: Monensin poisoning in ostriches. J S Afr Vet Assoc. 1999 Dec;70(4):140. [Article]
  9. van de Kerk P: [Monensin poisoning in horses]. Tijdschr Diergeneeskd. 1978 Jul 1;103(13):699-700. [Article]
  10. Kemp J: Monensin poisoning in turkeys. Vet Rec. 1978 May 27;102(21):467. [Article]
  11. Zizek S, Hrzenjak R, Kalcher GT, Srimpf K, Semrov N, Zidar P: Does monensin in chicken manure from poultry farms pose a threat to soil invertebrates? Chemosphere. 2011 Apr;83(4):517-23. doi: 10.1016/j.chemosphere.2010.12.058. Epub 2011 Jan 6. [Article]
KEGG Drug
D08228
KEGG Compound
C06693
ChemSpider
389937
RxNav
1368208
ChEBI
27617
ChEMBL
CHEMBL256105
ZINC
ZINC000008143466
Wikipedia
Monensin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PowderOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00633 mg/mLALOGPS
logP2.7ALOGPS
logP4.82ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area153.37 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity172.38 m3·mol-1ChemAxon
Polarizability73.59 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Park SW, Lomri N, Simeoni LA, Fruehauf JP, Mechetner E: Analysis of P-glycoprotein-mediated membrane transport in human peripheral blood lymphocytes using the UIC2 shift assay. Cytometry A. 2003 Jun;53(2):67-78. doi: 10.1002/cyto.a.10039. [Article]

Drug created at February 25, 2016 18:43 / Updated at February 21, 2021 18:53