NAV

Robenidine

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

Identification

Generic Name
Robenidine
DrugBank Accession Number
DB11542
Background

Robenidine is identified as a coccidiostat drug, which slows both the growth and reproductive cycles of coccidian parasites. Robenidine is used to control coccidiosis, a lethal infection in poultry which has shown a significant economic burden. Despite the availability of other agents to treat coccidiosis, robenidine has been proven to be effective in delaying the development of antibiotic resistance through intermittent and rotating use with other antimicrobials. Farmers alternate the use of robenidine with other antimicrobial agents in order to maintain effectiveness by slowing the development of antimicrobial resistance.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
3D
Similar Structures
Weight
Average: 334.2
Monoisotopic: 333.0548008
Chemical Formula
C15H13Cl2N5
Synonyms
  • Robenidina
  • Robenidine
  • Robenidinum
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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.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Robenidine hydrochloride8STT15Y39225875-50-7LTWIBTYLSRDGHP-HCURTGQUSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Chlorobenzenes
Alternative Parents
Aryl chlorides / Hydrazidines / Guanidines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Guanidine / Hydrazidine / Hydrocarbon derivative / Organic nitrogen compound / Organochloride / Organohalogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
4888ME6C4E
CAS number
25875-51-8
InChI Key
MOOFYEJFXBSZGE-LQGKIZFRSA-N
InChI
InChI=1S/C15H13Cl2N5/c16-13-5-1-11(2-6-13)9-19-21-15(18)22-20-10-12-3-7-14(17)8-4-12/h1-10H,(H3,18,21,22)/b19-9+,20-10+
IUPAC Name
N,N'-bis[(E)-[(4-chlorophenyl)methylidene]amino]guanidine
SMILES
ClC1=CC=C(\C=N\NC(=N)N\N=C\C2=CC=C(Cl)C=C2)C=C1

References

General References
  1. McLoughlin DK, Chute MB: Robenidine resistance in Eimeria tenella. J Parasitol. 1978 Oct;64(5):874-7. [Article]
  2. Zagar JB, Ascione PP, Chrekian GP: Automated high-pressure liquid chromatographic assay of robenidine hydrochloride. J Assoc Off Anal Chem. 1975 Jul;58(4):822-7. [Article]
  3. Peeters JE, Geeroms R: Efficacy of diclazuril against robenidine resistant Eimeria magna in rabbits. Vet Rec. 1989 Jun 3;124(22):589-90. [Article]
  4. Peeters JE, Geeroms R, Norton CC: Eimeria magna: resistance against robenidine in the rabbit. Vet Rec. 1987 Dec 5;121(23):545-6. [Article]
  5. Peeters JE, Halen P: Robenidine treatment of rabbits naturally infected with coccidia. Lab Anim. 1980 Jan;14(1):53-4. [Article]
  6. Wilga J, Wasik AK, Namiesnik J: Comparison of extraction techniques of robenidine from poultry feed samples. Talanta. 2007 Oct 31;73(5):812-9. doi: 10.1016/j.talanta.2007.04.046. Epub 2007 May 10. [Article]
  7. Joyner LP, Norton CC: Robenidine-dependence in a strain of Eimeria maxima. Parasitology. 1975 Feb;70(1):47-51. [Article]
  8. Peeters JE, Halen P, Meulemans G: Efficacy of robenidine in the prevention of rabbit coccidiosis. Br Vet J. 1979 Jul-Aug;135(4):349-54. [Article]
  9. Bakhtari SK, Jira J: Chemotherapy of experimental toxoplasmosis with special reference to robenidine. Folia Parasitol (Praha). 1988;35(3):193-8. [Article]
  10. Berger H, Wang GT, Shor AL, Gale GO, Simkins KL: Safety evaluation of robenidine in the feed of broiler chickens. Poult Sci. 1974 May;53(3):1013-5. [Article]
KEGG Drug
D08486
ChemSpider
7844905
RxNav
1311554
ChEMBL
CHEMBL97137
ZINC
ZINC000002013227
Wikipedia
Robenidine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00865 mg/mLALOGPS
logP1.98ALOGPS
logP4.38Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.71Chemaxon
pKa (Strongest Basic)4.99Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area72.63 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity122.65 m3·mol-1Chemaxon
Polarizability33.91 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001j-1911000000-777c9838d3f974a830ce
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001r-0907000000-780bd8d7441761d5b0e1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a70-0900000000-a3ec52dd978c227cbccb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0553-0900000000-a8058256dc53a5ad0fca
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000l-0900000000-80493ad10972c59e869f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-055r-0901000000-95f7c8a9efaed5de035e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0907000000-f1da5a5c49962b7d5fad
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-9600000000-37981bb0866f46e8f80b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-0901000000-82ebf9e44db52e9f92b6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-9000000000-841d84508e01846aa616
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-fd788428c0d05fa4a2d5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-9000000000-bffcdb15a65f2551842e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-184.83678
predicted
DeepCCS 1.0 (2019)
[M+H]+187.19478
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.86977
predicted
DeepCCS 1.0 (2019)

Drug created at February 26, 2016 17:41 / Updated at February 21, 2021 18:53