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Details

Stereochemistry ACHIRAL
Molecular Formula C11H15ClN4O2
Molecular Weight 270.715
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NITENPYRAM

SMILES

CCN(CC1=CC=C(Cl)N=C1)C(\NC)=C\[N+]([O-])=O

InChI

InChIKey=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+

HIDE SMILES / InChI

Molecular Formula C11H15ClN4O2
Molecular Weight 270.715
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Nitenpyram is a neonicotinoid, a neurotoxin that blocks neural messages and used in agriculture and veterinary medicine to kill external parasites of pets. Imidacloprid act as agonists at the insect nicotinic acetylcholine receptor (nAChR). The botanical insecticide nicotine acts at the same target without the neonicotinoid level of effectiveness or safety. Fundamental differences between the nAChRs of insects and mammals confer remarkable selectivity for the neonicotinoids. Whereas ionized nicotine binds at an anionic subsite in the mammalian nAChR, the negatively tipped ("magic" nitro or cyano) neonicotinoids interact with a proposed unique subsite consisting of cationic amino acid residue(s) in the insect nAChR. Nitenpyram was introduced into the United States in 1994 as a veterinary flea control treatment, structural pest and crop insecticide, and seed treatment. It has been used orally in dogs, cats, and some wildlife species for over 10 years. After ingestion, it begins killing adult fleas within 30 minutes, and effects continue for up to 48 hours. Though nitenpyram is used to kill adult fleas quickly on an infected animal, it does not kill insect eggs and has no long-term activity. Thus, it is not effective as a long-term flea preventative; however, it can be repeatedly applied over the course of several days to eradicate a single instance of infestation. Nitenpyram can be combined with a longer-term flea preventative like fipronil or lufenuron to prevent reinfestation. Neonicotinoids for veterinary use are considered to have a low order of toxicity for domestic animals and there are no reports of nitenpyram intoxication.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
capstar

Sample Use Guides

In Vivo Use Guide
For dogs and cats -- 11.4-57mg/day
Route of Administration: Oral
In Vitro Use Guide
Xenopus laevis oocytes were used for activity evaluation. Stock solutions of imidacloprid (1 mM), CH-IMI (10 mM), DN-IMI (10 mM) and nitenpyram (100 mM) in SOS were stored at 4 C. To suppress any possible endogenous muscarinic response, saline containing 0.5 M atropine was employed. Using two-electrode voltage-clamp electrophysiology, membrane currents were recorded by a GENECLAMP 500B (Axon Instruments, Union City, CA, USA) amplifier at a membrane potential of -100 mV. Current signals were displayed on a pen recorder. Oocytes were challenged with test compounds at intervals of 3–5 min to minimize effects of desensitization. Concentration-response data were obtained, not only by challenging oocytes with increasing concentrations of either ACh or neonicotinoid, but also by deploying decreasing concentrations of the compounds under test in order to confirm the validity of the concentration-response curve. The maximum amplitude of the current recorded in response to each challenge was normalized to the maximum amplitude of the current response to ACh
Substance Class Chemical
Record UNII
3A837VZ81Y
Record Status Validated (UNII)
Record Version