Narasin

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

Identification

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Name
Narasin
Accession Number
DB11432
Type
Small Molecule
Groups
Experimental, Vet approved
Description

Narasin is an agent with coccidiostatic and antibacterial properties.

Structure
Thumb
Synonyms
  • Narasin
  • Narasin A
  • Narasine
  • Narasino
  • Narasinum
External IDs
C 7819B / C-7819B / COMPD-79891 / Lilly 79891
International/Other Brands
Monteban (veterinary)
Categories
UNII
DZY9VU539P
CAS number
55134-13-9
Weight
Average: 765.038
Monoisotopic: 764.507463138
Chemical Formula
C43H72O11
InChI Key
VHKXXVVRRDYCIK-CWCPJSEDSA-N
InChI
InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)/t23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,36+,37+,38-,40-,41+,42-,43-/m0/s1
IUPAC Name
(2R)-2-[(2R,3S,5S,6R)-6-[(2S,3S,4S,6R)-6-[(2S,5S,7R,9S,10S,12R,15R)-2-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5^{7}.3^{5}]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-3,5-dimethyloxan-2-yl]butanoic acid
SMILES
[H][C@@]1(CC[C@](O)(CC)[C@H](C)O1)[C@]1(C)CC[C@]2(O1)O[C@@]1(O[C@]([H])([C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)[C@]3([H])O[C@@]([H])([C@@H](CC)C(O)=O)[C@@H](C)C[C@@H]3C)[C@@H](C)C[C@H]1C)C=C[C@H]2O

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Narasin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Narasin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Narasin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Narasin is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Narasin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Narasin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Narasin.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Narasin.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Narasin.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Narasin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Behr KP, Luders H, Glunder G, Friederichs M: [Narasin poisoning in turkeys]. Dtsch Tierarztl Wochenschr. 1988 Mar;95(3):107-8, 110-1. [PubMed:3289887]
  2. Salyi G, Szabo E, Bago G, Banhidi G, Szilagyi M: Narasin poisoning in turkeys. Acta Vet Hung. 1988;36(1-2):107-15. [PubMed:3202044]
  3. Litjens JB: [A case of narasin poisoning in turkeys]. Tijdschr Diergeneeskd. 1985 Sep 1;110(17):665. [PubMed:4060134]
  4. Van Halderen A, Bastianello SS, Fourie N, Zumpt IF: An outbreak of narasin poisoning in swine. J S Afr Vet Assoc. 1993 Mar;64(1):43-6. [PubMed:8496896]
  5. Salles MS, Lombardo de Barros CS, Barros SS: Ionophore antibiotic (narasin) poisoning in rabbits. Vet Hum Toxicol. 1994 Oct;36(5):437-44. [PubMed:7839570]
  6. Jeffers TK, Tonkinson LV, Camp LJ, Murphy CN, Schlegel BF, Snyder DL, Young DC: Field experience trials comparing narasin and monensin. Poult Sci. 1988 Jul;67(7):1058-61. [PubMed:3222193]
  7. Jeffers TK, Tonkinson LV, Callender ME: Anticoccidial efficacy of narasin in battery cage trials. Poult Sci. 1988 Jul;67(7):1043-9. [PubMed:3222191]
  8. Hussey RL, Macy TD, Moran J, Loh A: Liquid chromatographic determination of narasin in feed premixes. J Assoc Off Anal Chem. 1985 May-Jun;68(3):417-8. [PubMed:4019361]
  9. Occolowitz JL, Berg DH, Debono M, Hamill RL: The structure of narasin and a related ionophore. Biomed Mass Spectrom. 1976 Dec;3(6):272-7. [PubMed:1000056]
  10. Jeffers TK, Tonkinson LV, Callender ME, Schlegel BF, Reid WM: Anticoccidial efficacy of narasin in floor pen trials. Poult Sci. 1988 Jul;67(7):1050-7. [PubMed:3222192]
External Links
KEGG Drug
D05122
ChemSpider
58911
ChEMBL
CHEMBL2104423
Wikipedia
Narasin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00241 mg/mLALOGPS
logP4.7ALOGPS
logP7.88ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area161.21 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity204.54 m3·mol-1ChemAxon
Polarizability85.69 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

Taxonomy

Description
This compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Terpene glycosides
Direct Parent
Diterpene glycosides
Alternative Parents
Diterpenoids / Fatty alcohols / Branched fatty acids / Heterocyclic fatty acids / Hydroxy fatty acids / Ketals / Beta-hydroxy ketones / Oxanes / Pyrans / Tertiary alcohols
show 8 more
Substituents
Diterpene glycoside / Diterpenoid / Fatty alcohol / Ketal / Branched fatty acid / Heterocyclic fatty acid / Hydroxy fatty acid / Beta-hydroxy ketone / Fatty acyl / Pyran
show 20 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on February 25, 2016 11:44 / Updated on June 04, 2019 07:21