Nitenpyram   中文名称: 烯啶虫胺

体外活性：烯啶虫胺是一种烟碱乙酰胆碱受体 (AchR) 激动剂，用作治疗牲畜和宠物寄生虫的兽药。烯啶虫胺是武田药品工业株式会社开发的一种以2,2-双(氨基)硝基乙烯为基本结构的新型烟碱类杀虫剂，对飞虱、叶蝉、蚜虫等半翅目害虫具有显着效果。 ，具有作用快、持久、内吸、对植物安全等特点。

对于狗和猫，口服烯啶虫胺（1 mg/kg）可在短时间内控制跳蚤。治疗 30 分钟后，动物身上的跳蚤开始脱落，一剂即可使动物安全一到两天[1]。由于烯啶虫胺具有很强的亲脂性，因此饭后口服可刺激胆汁流动，从而有助于溶解该物质并改善胃肠道对药物的吸收。当狗和猫口服时，它会在 90 分钟内从胃肠道快速完全吸收，并在 48 小时内完全通过尿液排出。在肝脏中，吡啶虫胺被羟基化，然后结合。烯啶虫胺不会在身体组织中积聚；相反，它的结合物会通过尿液排出。在狗和猫中，烯啶虫胺的血浆半衰期分别为 3 小时和 8 小时。在患有肝脏和/或肾脏问题的动物中，烯啶虫胺的血浆半衰期可能会延长[1]。

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.

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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.

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Biological Half-Life
Elimination half-lives /after oral dosing/ are: approximately 3 hours for dogs; 8 hours for cats.

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.

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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.

[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.

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).

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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.

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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.

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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.

C11H15CLN4O2

270.72

270.088

150824-47-8

3034287

Light yellow to yellow solid powder

1.3±0.1 g/cm3

417.2±45.0 °C at 760 mmHg

72ºC

206.1±28.7 °C

0.0±1.0 mmHg at 25°C

1.568

1.9

73.98

1

5

5

18

306

0

CCN(CC1=CN=C(C=C1)Cl)/C(=C/[N+](=O)[O-])/NC

CFRPSFYHXJZSBI-DHZHZOJOSA-N

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+

(E)-1-N'-[(6-chloropyridin-3-yl)methyl]-1-N'-ethyl-1-N-methyl-2-nitroethene-1,1-diamine

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

注意： 本产品在运输和储存过程中需避光。

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

配方 1 中的溶解度: ≥ 2.08 mg/mL (7.68 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将100 μL 20.8 mg/mL澄清DMSO储备液加入400 μL PEG300中，混匀；然后向上述溶液中加入50 μL Tween-80，混匀；加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 2.08 mg/mL (7.68 mM) (饱和度未知) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 20.8 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 3 中的溶解度: ≥ 2.08 mg/mL (7.68 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 20.8 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。