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Monepantel
Last updated: 18/05/2024
(Not known by any other names)

GENERAL INFORMATION
Description
A broad spectrum anthelmintic veterinary drug
Availability status
Current
Introduction & key dates
2009, Switzerland
Examples of veterinary uses
Used to control and treat gastro-intestinal roundworms
Examples of species treated
Sheep; Goats
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved
EU Regulatory approval status
Approved
Chemical structure
Isomerism
Isomeric
Chemical formula
C₂₀H₁₃F₆N₃O₂S
Canonical SMILES
CC(COC1=C(C=CC(=C1)C#N)C(F)(F)F)(C#N)NC(=O)C2=CC=C(C=C2)SC(F)(F)F
Isomeric SMILES
C[C@@](COC1=C(C=CC(=C1)C#N)C(F)(F)F)(C#N)NC(=O)C2=CC=C(C=C2)SC(F)(F)F
International Chemical Identifier key (InChIKey)
WTERNLDOAPYGJD-GOSISDBHSA-N
International Chemical Identifier (InChI)
InChI=1S/C20H13F6N3O2S/c1-18(10-28,11-31-16-8-12(9-27)2-7-15(16)19(21,22)23)29-17(30)13-3-5-14(6-4-13)32-20(24,25)26/h2-8H,11H2,1H3,(H,29,30)/t18-/m1/s1
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
monepantel -
General status
Veterinary substance type
Nematicide, Antiparasitic, Anthelmintic, Medicinal drug
Substance groups
Amino-acetonitrile derivative
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Paralyses worms by attacking a previously undiscovered receptor - Hco-MPTL-1 - only present in nematodes
Molecular targets
[Nicotinic acetylcholine receptor, Blocker]
CAS RN
887148-69-8
EC number
-
CIPAC number
-
US EPA chemical code
-
PubChem CID
-
Therapeutic Class
Antiparasitic products, insecticides & repellents: anthelmintics
ATCvet Code
QP52AX09
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: Ovine, Caprine)
Molecular mass
473.39
PIN (Preferred Identification Name)
-
IUPAC name
N-(2-cyano-1[(2S)-5-cyano-2-(trifluoromethyl)phenoxy)propan-2-yl)-4-(trifluoromethylsulfanyl)benzamide
CAS name
N-[(1S)-1-cyano-2-(5-cyano-2-fluoromethylphenoxy)-1-methylethyl]-4-trifluoromethylsulfanylbenzamid
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
White powdery solid
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Zolvix 25 mg/ml Oral Solution for Sheep Elanco GmbH GB National authorisation Prescription only medicine to be authorised by a registered, qualified person (POM-VPS)
Formulation and application details
Usually formulated as oral solutions
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.08
E4 E = Manufacturers safety data sheets
4 = Verified data
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
6900
E4 E = Manufacturers safety data sheets
4 = Verified data
Propylene glycol
-
7300
E4 E = Manufacturers safety data sheets
4 = Verified data
n-Octanol
-
60700
E4 E = Manufacturers safety data sheets
4 = Verified data
Ethanol
-
175000
E4 E = Manufacturers safety data sheets
4 = Verified data
Dichloromethane
-
Melting point (°C)
145
E4 E = Manufacturers safety data sheets
4 = Verified data
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.82 X 1004 Calculated -
Log P
4.45
E4 E = Manufacturers safety data sheets
4 = Verified data
High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.468
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
2.8 X 10-06
E4 E = Manufacturers safety data sheets
4 = Verified data
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
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)
92
E4 E = Manufacturers safety data sheets
4 = Verified data
Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
DT₅₀ ranges 38-146 days, rate depends on sand fraction in soil: less sand = faster degradation
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
Stable
E4 E = Manufacturers safety data sheets
4 = Verified data
Stable
Note
Stable under normal environmental conditions
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
E4 E = Manufacturers safety data sheets
4 = Verified data
Stable
Note
Stable under normal environmental conditions
Water-sediment DT₅₀ (days)
- - -
Water 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)
-
E4 E = Manufacturers safety data sheets
4 = Verified data
Non-mobile
Koc (mL g⁻¹)
7481
Notes and range
Koc range 6082-8880 mL g⁻¹, Soils=5
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
0.25 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
monepantel sulfone - - -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 2000
E4 E = Manufacturers safety data sheets
4 = Verified data
Rat
Low
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)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
2.4
E4 E = Manufacturers safety data sheets
4 = Verified data
Eisenia foetida 56 day
Moderate
Soil micro-organisms
[No impact up to 0.3 mg kg⁻¹ soil]
E4 E = Manufacturers safety data sheets
4 = Verified data
-
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)
- - -
Chronic
- - -
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)
- - -
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)
-
E2 E = Manufacturers safety data sheets
2 = Unverified data of unknown source
Non-toxic
-
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)
-
E2 E = Manufacturers safety data sheets
2 = Unverified data of unknown source
Non-toxic
-
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)
-
E2 E = Manufacturers safety data sheets
2 = Unverified data of unknown source
Non-toxic
-
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 - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
- - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 2000
E4 E = Manufacturers safety data sheets
4 = Verified data
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
E4 E = Manufacturers safety data sheets
4 = Verified data
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
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
May be absorbed through the skin
Mammalian dose elimination route and rate
Excretion was mainly via the faeces as metabolites following intravenous administration, but over 50% remains in unchanged form following oral administration
E4 E = Manufacturers safety data sheets
4 = Verified data
-
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
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
No data found
Yes, known to cause a problem
?Possibly, status not identified
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
Possible liver and kidney toxicant
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
-
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
monepantel
French
monepantel
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-

Record last updated: 18/05/2024
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