NAV

Nitenpyram

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

Identification

Generic Name
Nitenpyram
DrugBank Accession Number
DB11438
Background

Nitenpyram is an insecticide used in agriculture and veterinary medicine to kill external parasites of pets. It is a neonicotinoid, a neurotoxin that blocks neural messages and binds particularly tightly in the central nervous system of insects, causing rapid death.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
3D
Similar Structures
Weight
Average: 270.72
Monoisotopic: 270.0883534
Chemical Formula
C11H15ClN4O2
Synonyms
  • (1E)-N-((6-chloro-3-pyridinyl)methyl)-N-ethyl-N'-methyl-2-nitro-1,1-ethenediamine
  • (E)-nitenpyram
External IDs
  • TI 304
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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

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2-halopyridines. These are organic compounds containing a pyridine ring substituted at the 2-position by a halogen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Halopyridines
Direct Parent
2-halopyridines
Alternative Parents
Aryl chlorides / Heteroaromatic compounds / C-nitro compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Organic oxides
show 1 more
Substituents
2-halopyridine / Allyl-type 1,3-dipolar organic compound / Amine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / C-nitro compound / Heteroaromatic compound / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
chloropyridyl insecticide, nitenpyram (CHEBI:39170) / Neonicotinoid insecticides (C18511)
Affected organisms
Not Available

Chemical Identifiers

UNII
3A837VZ81Y
CAS number
150824-47-8
InChI Key
CFRPSFYHXJZSBI-DHZHZOJOSA-N
InChI
InChI=1S/C11H15ClN4O2/c1-3-15(11(13-2)8-16(17)18)7-9-4-5-10(12)14-6-9/h4-6,8,13H,3,7H2,1-2H3/b11-8+
IUPAC Name
[(E)-1-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-2-nitroethenyl](methyl)amine
SMILES
[H]C(=C(NC)N(CC)CC1=CN=C(Cl)C=C1)N(=O)=O

References

General References
  1. Zhang G, Nie S, Long L, Zeng D, Chen J, Yang H, Chen L: [Determination of nitenpyram residue in cabbage and soil using gas chromatography]. Se Pu. 2010 Nov;28(11):1103-6. [Article]
  2. Dobson P, Tinembart O, Fisch RD, Junquera P: Efficacy of nitenpyram as a systemic flea adulticide in dogs and cats. Vet Rec. 2000 Dec 16;147(25):709-13. [Article]
  3. Li SP, Jiang YY, Cao XH, Dong YW, Dong M, Xu J: Degradation of nitenpyram pesticide in aqueous solution by low-temperature plasma. Environ Technol. 2013 May-Jun;34(9-12):1609-16. [Article]
  4. Rust MK, Waggoner MM, Hinkle NC, Stansfield D, Barnett S: Efficacy and longevity of nitenpyram against adult cat fleas (Siphonaptera: Pulicidae). J Med Entomol. 2003 Sep;40(5):678-81. [Article]
  5. Wieland-Berghausen S, Schote U, Frey M, Schmidt F: Comparison of microencapsulation techniques for the water-soluble drugs nitenpyram and clomipramine HCl. J Control Release. 2002 Dec 13;85(1-3):35-43. [Article]
  6. Miller PF, Peters BA, Hort CA: Comparison of lufenuron and nitenpyram versus imidacloprid for integrated flea control. Vet Ther. 2001 Fall;2(4):285-92. [Article]
  7. Schenker R, Tinembart O, Humbert-Droz E, Cavaliero T, Yerly B: Comparative speed of kill between nitenpyram, fipronil, imidacloprid, selamectin and cythioate against adult Ctenocephalides felis (Bouche) on cats and dogs. Vet Parasitol. 2003 Mar 10;112(3):249-54. [Article]
  8. Sun C, Xu X, Xu Y, Yan D, Fang T, Liu T: Synthesis, insecticidal activity, and molecular docking studies of nitenpyram analogues with a flexible ester arm anchored on tetrahydropyrimidine ring. J Agric Food Chem. 2011 May 11;59(9):4828-35. doi: 10.1021/jf1049563. Epub 2011 Apr 15. [Article]
  9. Dryden MW, Magid-Denenberg T, Bunch S, Boyer J, Schenker R: Control of fleas on dogs and cats and in homes with the combination of oral lufenuron and nitenpyram. Vet Ther. 2001 Summer;2(3):208-14. [Article]
  10. Obana H, Okihashi M, Akutsu K, Kitagawa Y, Hori S: Determination of acetamiprid, imidacloprid, and nitenpyram residues in vegetables and fruits by high-performance liquid chromatography with diode-array detection. J Agric Food Chem. 2002 Jul 31;50(16):4464-7. [Article]
KEGG Compound
C18511
ChemSpider
2298774
RxNav
341379
ChEBI
39170
ChEMBL
CHEMBL259728
ZINC
ZINC000002381598
Wikipedia
Nitenpyram

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 Solubility0.317 mg/mLALOGPS
logP0.57ALOGPS
logP1.87Chemaxon
logS-2.9ALOGPS
pKa (Strongest Basic)3.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area73.98 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity80.77 m3·mol-1Chemaxon
Polarizability26.52 Å3Chemaxon
Number of Rings1Chemaxon
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-158.29924
predicted
DeepCCS 1.0 (2019)
[M+H]+160.65721
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.75038
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:47 / Updated at June 12, 2020 16:53