Nitenpyram (Ref: CGA 246916)	Last updated: 24/07/2024
(Also known as: (E)-nitenpyram ; TI 204; niterndipoine)

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GENERAL INFORMATION

Description	A systemic insecticide used mainly to kill external parasites in livestock and domestic pets
Availability status	Current
Introduction & key dates	1989 discovered, 1995 launched
Examples of veterinary uses	Mainly used to treat adult flea infestations in mammals and maggot infestations on reptiles as off-label
Examples of species treated	Cats; Dogs; Reptiles

Approval status

VMR 2013/2033 approval status (GB/UK)	Approved
EU Regulatory approval status	Approved

Chemical structure

Isomerism	Isomeric - molecule has one E/Z centre
Chemical formula	C₁₁H₁₅ClN₄O₂
Canonical SMILES	CCN(CC1=CN=C(C=C1)Cl)C(=C[N+](=O)[O-])NC
Isomeric SMILES	CCN(CC1=CN=C(C=C1)Cl)/C(=C/[N+](=O)[O-])/NC
International Chemical Identifier key (InChIKey)	CFRPSFYHXJZSBI-DHZHZOJOSA-N
International Chemical Identifier (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+
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
nitenpyram	-

General status

Veterinary substance type	Insecticide, Antiparasitic
Substance groups	Neonicotinoid insecticide
Minimum active substance purity	>98%
Known relevant impurities	-
Substance origin	Semi-synthetic
Mode of action	Systemic with translaminar activity, stomach and contact action affecting insects nervous system. No long term activity. Nicotinic acetylcholine receptor (nAChR) channel blocker.
Molecular targets	[Nicotinic acetylcholine receptors, Binder]
CAS RN	150824-47-8
EC number	634-900-5
CIPAC number	None allocated
US EPA chemical code	-
PubChem CID	3034287
CLP index number	No data found
Therapeutic Class	Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents
ATCvet Code	QP53BX02
Controlled Drug?	No
Regulation 37/2010 MRL Classification	-
Molecular mass	270.72
PIN (Preferred Identification Name)	(1E)-N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-N'-methyl-2-nitroethene-1,1-diamine
IUPAC name	(E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N'-methyl-2-nitrovinylidenediamine
CAS name	(1E)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N'-methyl-2-nitro-1,1-ethenediamine
Other status information	PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards	-
Physical state	Pale yellow to orange crystalline solid

Formulations

Property	Product	Manufacturer	Authorisation Route	Legal Class (GB/UK)
Example products (past and present) using this active	Bob Martin Flea Tablets	Elanco Europe Ltd	UK National authorisation (IC)	Authorised veterinary medicine for general sale (AVM-GSL)
	Capstar 11.4mg Tablets for Cats and Small Dogs	Elanco Europe Ltd	GB National authorisation	Authorised veterinary medicine for general sale (AVM-GSL)
	Johnsons 4Fleas 57mg Tables for Dogs	Elanco Europe Ltd	UK National authorisation (IC)	Authorised veterinary medicine for general sale (AVM-GSL)
Formulation and application details	Usually supplied in tablet form for oral administration

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		570000	E4 E = Manufacturers safety data sheets 4 = Verified data	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		1000000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Methanol	-
		700000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Chloroform	-
		290000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Acetone	-
		4500	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Xylene	-
Melting point (°C)		72	E4 E = Manufacturers safety data sheets 4 = Verified data	-
Boiling point (°C)		417.2	E4 E = Manufacturers safety data sheets 4 = Verified data	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	2.19 X 10-01	Calculated	-
	Log P	-0.66	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source at 25 °C	Low
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		1.254	E4 E = Manufacturers safety data sheets 4 = Verified data	-
Dissociation constant pKa) at 25 °C		3.1	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
		-
Vapour pressure at 20 °C (mPa)		0.0011	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		3.54 X 10-13	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Non-volatile
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
Surface tension (mN m⁻¹)		-	-	-
Refractive Index		-	-	-
Environmental release		-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
Soil degradation (days) (aerobic)	DT₅₀ (typical)	8	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Non-persistent
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	Note	General literature states DT₅₀ 1-15 days
Manure DT₅₀ (days)		-	-	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	Stable	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Stable
	Note	Stable pH 3-7 at 25 °C; pH9 DT₅₀ = 2.9 days
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		-	-	-
Sediment phase only DT₅₀ (days)		-	-	-
Air degradation		As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source	Mobile
	Koc (mL g⁻¹)	60
	Notes and range	Estimated
Freundlich	Kf (mL g⁻¹)	-	-	-
	Kfoc (mL g⁻¹)	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		2.01	Calculated	Transition state
Bio-concentration factor	BCF (l kg⁻¹)	Low risk	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source Based on LogP < 3	Low risk
	CT₅₀ (days)	-		-

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction
2-(N-(6-chloro-3-pyridylmethyl)-N-ethyl-N-methylformamidine	3-CPMF	Plant	-
2-(N-(6-chloro-3-pyridylmethyl)-N-ethyl)amino-2-methyliminoacetic acid	2-CPMA	Plant	-

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		1575	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	-	-
	(ppm diet)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		1124	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Anas platyrhynchos	Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		32.2	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Soil micro-organisms		-	-	-
Collembola	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Non-target plants		-	-	-
		-	-	-
Honeybees (Apis spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	0.138	R4 R = Peer reviewed scientific publications 4 = Verified data	High
	Chronic	-	-	-
	Notes	-
Bumblebees (Bombus spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
		-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
		-
Mason bees (Osmia spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
Other bee species (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other bee species (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Beneficial insects (Ladybirds)		-	-	-
Beneficial insects (Lacewings) as Mortality, Contact LC₅₀ ppm		> 0.33	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data Chrysoperla carnea Larva	-
Beneficial insects (Parasitic wasps)		-	-	-
Beneficial insects (Predatory mites)		-	-	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		10	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Oncorhynchus mykiss	Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		10000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Daphnia magna	Low
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		-	-	-
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)		-	-	-
Aquatic plants (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)		-	-	-
Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		26	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Pseudokirchneriella subcapitata	Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-
Marine bivalves		-	-	-

HUMAN HEALTH AND PROTECTION

General

Property		Value	Source; quality score; and other information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		1575	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		2000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		5.8	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		-	-	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		-	-	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Routes	Public	-
	Occupational	-
Mammalian dose elimination route and rate		In mammals it is excreted mostly unchanged in the urine	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor No data found A0 A = Chromosome aberration (EFSA database) 0 = No data ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant XNo, known not to cause a problem No data found No data found Respiratory tract irritant Skin irritant Skin sensitiser ✓Yes, known to cause a problem XNo, known not to cause a problem No data found Eye irritant Phototoxicant   ✓Yes, known to cause a problem No data found
General human health issues		No further information available

Handling issues

Property	Value and interpretation
General	Corrosive
CLP classification 2013	Health: H302, H315, H319, H335 Environment: H400, H410
WHO Classification	II (Moderately hazardous)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	Limited shelf-life. Store at -20 DegC

TRANSLATIONS

Language	Name
English	nitenpyram
French	-
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	24/07/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242