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Nitenpyram

Alias: Nitenpyram;Capstar, Bestguard
Cat No.:V1166 Purity: ≥98%
Nitenpyram (trade names Capstar, Bestguard),an insect neurotoxin of the neonicotinoid class, is a fast and long-acting, and orally bioavailable nicotinic acetylcholine receptor (AchR) agonist with neural signaling-blocking activity.
Nitenpyram
Nitenpyram Chemical Structure CAS No.: 150824-47-8
Product category: AChR Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
2g
5g
Other Sizes
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Nitenpyram (trade names Capstar, Bestguard), an insect neurotoxin of the neonicotinoid class, is a fast and long-acting, and orally bioavailable nicotinic acetylcholine receptor (AchR) agonist with neural signaling-blocking activity. It has been widely used as a veterinary medication to treat adult flea infestations, also used to treat parasites of livestock and pets.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Nitenpyram is a nicotinic acetylcholine receptor (AchR) agonist, used as veterinary medicine to treat parasites of livestock and pets. Nitenpyram is a new type of neonicotinoid insecticide with 2,2-bis(amino)nitroethene as the base structure, which has been developed by Takeda Pharmaceutical Company Limited.It is remarkably effective against pests of order Hemiptera, such as planthoppers, leafhoppers and aphids, and characterized by fast action, long lasting and systemic properties as well as safety for plants.

ln Vivo
For dogs and cats, nitenpyram is given orally (1 mg/kg) to control fleas for a brief period of time. After 30 minutes of treatment, fleas begin to drop off of the animals, and one dose can keep animals safe for one to two days[1]. Because nitenpyram is so lipophilic, it is taken orally after meals to stimulate bile flow, which aids in dissolving the substance and improves gastrointestinal absorption of the medication. When given orally to dogs and cats, it is quickly and entirely absorbed from the GI tract in less than 90 minutes and entirely eliminated in the urine in 48 hours. In the liver, nitinpyram is hydroxylated and then conjugated. Nitenpyram does not build up in bodily tissues; instead, its conjugates are eliminated in the urine. In dogs and cats, the plasma half-life of nitenpyram is 3 and 8 hours, respectively. Nitenpyram's plasma half-life is probably prolonged in animals with liver and/or kidney issues[1].
Animal Protocol
1 mg/kg; oral
Dogs and cats
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Nitenpyram is rapidly and practically completely absorbed after oral administration. Peak levels occur approximately 80 minutes after dosing in dogs; approximately 40 minutes in cats. Elimination half-lives are: approximately 3 hours for dogs; 8 hours for cats. Nitenpyram is excreted primarily as conjugated metabolites in the urine and excretion is complete within 48 hours of dosing. In dogs, approximately 3% of a dose is excreted in feces; in cats approximately 5% is excreted in the feces.
Nitenpyram is administered PO in pill form to kill fleas in both dogs and cats. It is absorbed rapidly, with maximal blood concentrations reached within 1.2 hr and 0.6 hr in dogs and cats, respectively. ... The compound is rapidly eliminated, with >90% excreted in the urine within 24-48 hr, primarily as unchanged nitenpyram.
Metabolism / Metabolites
BACKGROUND: Nitenpyram is a member of the economically important neonicotinoid class of insecticides. The in vivo metabolism of nitenpyram is not well characterized, but cytochrome P450 activity is the major mechanism of resistance to neonicotinoids identified in insect pests, and P450s metabolize other neonicotinoids including imidacloprid. RESULTS: Here, we used the GAL4-UAS targeted expression system to direct RNA interference (RNAi) against the cytochrome P450 redox partners to interrupt P450 functions in specific tissues in Drosophila melanogaster. RNAi of the mitochondrial redox partner defective in the avoidance of repellents (dare) in the digestive tissues reduced nitenpyram mortality, suggesting an activation step in the metabolism of nitenpyram carried out by a mitochondrial P450. RNAi of the mitochondrial cytochrome P450 Cyp12a5, which is expressed in the digestive tissues, resulted in the same phenotype, and transgenic overexpression of Cyp12a5 increased nitenpyram sensitivity. CONCLUSION: These results suggest that in vivo metabolism of nitenpyram by the mitochondrial P450 CYP12A5 results in the formation of a product with higher toxicity than the parent compound.
Biological Half-Life
Elimination half-lives /after oral dosing/ are: approximately 3 hours for dogs; 8 hours for cats.
Toxicity/Toxicokinetics
Toxicity Summary
IDENTIFICATION AND USE: Nitenpyram is neonicotinoid insecticide that controls aphids, leafhoppers, thrips, whiteflies on rice and glasshouse crops. It is also used to control fleas in dogs and cats. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: The following adverse events are listed in decreasing order of reporting frequency. Cats: hyperactivity, panting, lethargy, itching, vocalization, vomiting, fever, decreased appetite, nervousness, diarrhea, difficulty breathing, salivation, incoordination, seizures, pupil dilation, increased heart rate, and trembling. Dogs: lethargy/depression, vomiting, itching, decreased appetite, diarrhea, hyperactivity, incoordination, trembling, seizures, panting, allergic reactions including hives, vocalization, salivation, fever, and nervousness. The frequency of serious signs, including neurologic signs and death, was greater in animals under 2 pounds of body weight, less than 8 weeks of age, and/or reported to be in poor body condition. In some instances, birth defects and fetal/neonatal loss were reported after treatment of pregnant and/or lactating animals. ECOTOXICITY STUDIES: The toxic effect of nitenpyram on the brain of juvenile Chinese rare minnows (Gobiocypris rarus) was investigated by determining the oxidative stress, and acetylcholinesterase (AChE) activity. The superoxide dismutase (SOD) activities did not significantly change after long-term exposure to nitenpyram. A noticeable increase of catalase (CAT) activities was observed on the brain tissues under nitenpyram treatments. The malondialdehyde (MDA) content increased markedly under 0.1 mg/L nitenpyram treatments. The AChE activities decreasing under 2.0 mg/L nitenpyram. Changes in the antioxidant enzyme activities in zebrafish are reported for nitenpyram. Nitenpyram was highly toxic to earthworm (Eisenia fetida), and can significantly inhibit fecundity and cellulase activity of E. fetida, and it was also damaging to the epidermal and midgut cells of earthworms.
Non-Human Toxicity Values
LD50 Rat (male) oral 1680 mg/kg
LD50 Rat (female) oral 1575 mg/kg
LD50 Rat (male) dermal >2000 mg/kg
LD50 Rat (female) dermal >2000 mg/kg
For more Non-Human Toxicity Values (Complete) data for Nitenpyram (6 total), please visit the HSDB record page.
References

[1]. Insect nicotinic acetylcholine receptor agonists as flea adulticides in small animals. J Vet Pharmacol Ther. 2010 Aug;33(4):315-22.

[2]. Efficacy and longevity of nitenpyram against adult cat fleas (Siphonaptera: Pulicidae). J Med Entomol. 2003 Sep;40(5):678-81.

Additional Infomation
Nitenpyram is a C-nitro compound consisting of 2-nitroethene-1,1-diamine where one of the nitrogens bears ethyl and (6-chloro-3-pyridinyl)methyl while the other nitrogen carries a methyl group. It has a role as a neonicotinoid insectide. It is a C-nitro compound and a monochloropyridine. It is functionally related to a 2-chloropyridine.
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.
Nitenpyram has been reported in Streptomyces canus with data available.
See also: Lufenuron; Nitenpyram (component of); Lufenuron; Milbemycin Oxime; Nitenpyram (component of).
Mechanism of Action
Nitenpyram is in the class of neonicotinoid insecticides. It enters the systemic circulation of the adult flea after consuming blood from a treated animal. It binds to nicotinic acetylcholine receptors in the postsynaptic membranes and blocks acetylcholine-mediated neuronal transmission causing paralysis and death of the flea. Nitenpyram is 3500x more selective for insect alpha-4beta-2 nicotinic receptors than in vertebrate receptors. It does not inhibit acetylcholinesterase.
Therapeutic Uses
VET: Nitenpyram inhibits the nicotinic acetylcholine receptor. It is used to treat Ctenocephalides spp in dogs and cats ... . It is toxic to fleas for only 24-48 hr and is normally used in combination with an insect growth regulator to provide continuous flea control.
VET: Nitenpyram is indicated as a flea adulticide in dogs and cats that are, at a minimum, 2 pounds in weight and 4 weeks old. It does not repel fleas or ticks and does not reliably kill ticks, flea eggs, larvae or immature fleas. Nitenpyram may be effective for treating fly larvae (maggots) of various species. Fleas begin to fall from treated animals about 30 minutes after dosing and a single dose can protect animals for 1-2 days.
Drug Warnings
VET: The following adverse events are based on post-approval adverse drug experience reporting. Not all adverse reactions are reported to FDA CVM. It is not always possible to reliably estimate the adverse event frequency or establish a causal relationship to product exposure using this data. The following adverse events are listed in decreasing order of reporting frequency. Cats: hyperactivity, panting, lethargy, itching, vocalization, vomiting, fever, decreased appetite, nervousness, diarrhea, difficulty breathing, salivation, incoordination, seizures, pupil dilation, increased heart rate, and trembling. Dogs: lethargy/depression, vomiting, itching, decreased appetite, diarrhea, hyperactivity, incoordination, trembling, seizures, panting, allergic reactions including hives, vocalization, salivation, fever, and nervousness. The frequency of serious signs, including neurologic signs and death, was greater in animals under 2 pounds of body weight, less than 8 weeks of age, and/or reported to be in poor body condition. In some instances, birth defects and fetal/neonatal loss were reported after treatment of pregnant and/or lactating animals.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H15CLN4O2
Molecular Weight
270.72
Exact Mass
270.088
CAS #
150824-47-8
Related CAS #
150824-47-8
PubChem CID
3034287
Appearance
Light yellow to yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
417.2±45.0 °C at 760 mmHg
Melting Point
72ºC
Flash Point
206.1±28.7 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.568
LogP
1.9
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Heavy Atom Count
18
Complexity
306
Defined Atom Stereocenter Count
0
SMILES
CCN(CC1=CN=C(C=C1)Cl)/C(=C/[N+](=O)[O-])/NC
InChi Key
CFRPSFYHXJZSBI-DHZHZOJOSA-N
InChi Code
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+
Chemical Name
(E)-1-N'-[(6-chloropyridin-3-yl)methyl]-1-N'-ethyl-1-N-methyl-2-nitroethene-1,1-diamine
Synonyms
Nitenpyram;Capstar, Bestguard
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:54 mg/mL (199.5 mM)
Water: N/A
Ethanol:54 mg/mL (199.5 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (7.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (7.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.6939 mL 18.4693 mL 36.9385 mL
5 mM 0.7388 mL 3.6939 mL 7.3877 mL
10 mM 0.3694 mL 1.8469 mL 3.6939 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Chemical structures of neonicotinoids. The neonicotinoids are nitromethylenes (C=CHNO2), nitroguanidines(C=NNO2), and cyanoamidines (C=NCN). Imidacloprid, nitenpyram, acetamiprid and thiacloprid belong to the first generation and the chloronicotinyl subclass. Thiamethoxam and clothianidin (the second generation neonicotinoids) are the thianicotinyl subclass and dinotefuran (the third generation neonicotinoids) is the furanicotinyl subclass (Modified from Tomizawa M, Casida JE. Annu Rev Pharmacol Toxicol 2005;45:247–268, Figure 1 with permission).[1].Insect nicotinic acetylcholine receptor agonists as flea adulticides in small animals. J Vet Pharmacol Ther. 2010 Aug;33(4):315-22.
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