NAV

Narasin

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

Identification

Generic Name
Narasin
DrugBank Accession Number
DB11432
Background

Narasin is an agent with coccidiostatic and antibacterial properties.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
Similar Structures
Weight
Average: 765.038
Monoisotopic: 764.507463138
Chemical Formula
C43H72O11
Synonyms
  • Narasin
  • Narasin A
  • Narasine
  • Narasino
  • Narasinum
External IDs
  • C 7819B
  • C-7819B
  • COMPD-79891
  • Lilly 79891
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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.
DrugInteraction
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interactions in your software
AcenocoumarolThe risk or severity of bleeding can be increased when Narasin is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Narasin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Narasin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Narasin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Narasin is combined with Benzocaine.
Food Interactions
Not Available

Products

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International/Other Brands
Monteban (veterinary)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Acetal / Alcohol / Aliphatic heteropolycyclic compound / Beta-hydroxy ketone / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Diterpene glycoside
show 20 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
DZY9VU539P
CAS number
55134-13-9
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

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. [Article]
  2. Salyi G, Szabo E, Bago G, Banhidi G, Szilagyi M: Narasin poisoning in turkeys. Acta Vet Hung. 1988;36(1-2):107-15. [Article]
  3. Litjens JB: [A case of narasin poisoning in turkeys]. Tijdschr Diergeneeskd. 1985 Sep 1;110(17):665. [Article]
  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. [Article]
  5. Salles MS, Lombardo de Barros CS, Barros SS: Ionophore antibiotic (narasin) poisoning in rabbits. Vet Hum Toxicol. 1994 Oct;36(5):437-44. [Article]
  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. [Article]
  7. Jeffers TK, Tonkinson LV, Callender ME: Anticoccidial efficacy of narasin in battery cage trials. Poult Sci. 1988 Jul;67(7):1043-9. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
KEGG Drug
D05122
ChemSpider
58911
RxNav
1314370
ChEMBL
CHEMBL2104423
ZINC
ZINC000085540282
Wikipedia
Narasin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GranuleOral
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/MSsplash10-00mk-0000000900-8237f0689cabfb349717
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0000001900-baf2864af136ef1dcd36
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0401-0300502900-811c8c3364d5c6009c4d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xr-1000073900-2cb893ef0b51754409f9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06dr-7210039200-ea7da2d244083ee437a4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03ds-7471295500-854e6509eeee04476e63
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-315.9728249
predicted
DarkChem Lite v0.1.0
[M-H]-252.44041
predicted
DeepCCS 1.0 (2019)
[M+H]+315.4761249
predicted
DarkChem Lite v0.1.0
[M+H]+254.16411
predicted
DeepCCS 1.0 (2019)
[M+Na]+314.4203249
predicted
DarkChem Lite v0.1.0
[M+Na]+260.49307
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:44 / Updated at February 21, 2021 18:53