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
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
Forever chemical	-
Other status information	PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards	-
Physical state	Pale yellow to orange crystalline solid

Commercial

Property	Product	Manufacturer	Authorisation Route	Legal Class (GB/UK)
Availability status	Current
Introduction & key dates	1989 discovered, 1995 launched
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	Vegetative vigour ER₅₀ (g ha⁻¹)	-	-	-
	Seedling emergence ER₅₀ (g ha⁻¹)	-	-	-
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, fonds growth, fresh) - 7 day (mg l⁻¹)		-	-	-
Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)		-	-	-
Algae - Acute (growth rate, fresh; mg l⁻¹) (EC₅₀)		26.0	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Raphidocelis subcapitata	Low
Algae - Chronic (growth rate, fresh; 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