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Levamisole
Last updated: 24/06/2022
(Also known as: tetramisole ; levomysol; L-tetramisole)

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate Ecotoxicity Human health
Environmental fate
Low alert:
Drainflow: Non-mobile
Warning:
Significant data are missing
Ecotoxicity
Low alert:
Fish acute ecotoxicity: Low
Warning:
Significant data are missing
Human health
Moderate alert:
Mammals acute toxicity: Moderate; Possible Reproduction/development effects; Neurotoxicant
GENERAL INFORMATION
Description
Used mainly as a dewormer in livestock and for freshwater tropical fish
Availability status
-
Introduction & key dates
1966, discovered
Examples of species treated
Cattle, Pigs, Sheep, Freshwater tropical fish, Elephants
Chemical structure
Isomerism
Levamisole is the biologically active isomer of the isomeric tetramisole
Chemical formula
C₁₁H₁₂N₂S
Canonical SMILES
C1CSC2=NC(CN21)C3=CC=CC=C3
Isomeric SMILES
C1CSC2=N[C@H](CN21)C3=CC=CC=C3
International Chemical Identifier key (InChIKey)
HLFSDGLLUJUHTE-SNVBAGLBSA-N
International Chemical Identifier (InChI)
InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
levamisole -
levamisole hydrochloride Variant
General status
Veterinary substance type
Dewormer, Antiparasitic, Anthelmintic
Substance groups
Imidazothiazole
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Works by causing parasitic paralysis allowing it to be expelled. Nicotinic receptor agonist.
Molecular targets
[Neuronal acetylcholine receptor subunit alpha-3, agonist], [Alkaline phosphatase, placental-like, antagonist]
CAS RN
14769-73-4
EC number
238-836-5
CIPAC number
-
US EPA chemical code
-
PubChem CID
-
ATCvet Code
QP52AE01
Therapeutic Class
Antiparasitic products, insecticides & repellents: Anthelmintics
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: Bovine, Ovine, Porcine, Poultry)
Molecular mass
204.29
PIN (Preferred Identification Name)
-
IUPAC name
(S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
CAS name
-
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
White solid
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
UK Legal Class
Example products using this active
Charnaverm 7.5% oral solution Chanelle Animal Health Ltd UK National authorisation Prescription only medicine to be authorised by suitably qualified person (POM-VPS)
Combinex oral solution Novartis Animal Health UK Ltd UK National authorisation Prescription only medicine to be authorised by suitably qualified person (POM-VPS)
Levafas diamand oral suspension Norbrook labs UK National authorisation Prescription only medicine to be authorised by suitably qualified person (POM-VPS)
Levitape oral suspension for sheep Merial Animal Health Ltd UK National authorisation Prescription only medicine to be authorised by suitably qualified person (POM-VPS)
Formulation and application details
Available in a variety of formulations including topically applied solutions, oral solutions and solutions for injection
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
1120
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
60
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
6.92 X 1001 Calculated -
Log P
1.84
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.31
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
14.76
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Highly volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
-
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
R4 R = Peer reviewed scientific publications
4 = Verified data
Non-mobile
Koc
8652
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
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
Metabolising enzymes
Ref: R92535 - Rat; Dog, Monkey (Urine) - -
4-[(6S)-2,3,5,6-tetrahydroimidazol[2,1-b)thiazol-6-yl]phenol (Ref: R9313) p-hydroxylevamisole; p-OH-levamisole Humans; Rat; Dog; Monkey (Urine) - -
Ref: R43837 - Dog; Monkey (Urine) - -
Ref: R43037 - Dog (Urine) - -
Ref: R8418 - Dog - -
Ref: R9280 - Dog - -
Ref: R45714 - - - -
(RS)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
Note: Pharmaceutically active
Aminorex Horse (Urine) - -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
180
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
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)
- - -
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)
- - -
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)
- - -
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 pollinators (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other pollinators (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
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 1750
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Anguilla spp.
Low
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic invertebrates - Chronic 21 day NOEC (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 - 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)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
180
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
Subcutaneous LD₅₀ = 120 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
Intravenous LD₅₀ = 24 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
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
High level of metabolism, less than 6% excreted unchanged in urine, metabolites excreted in both urine and faeces
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
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
;
E2 E = Unspecified genotoxicity type (miscellaneous data source)
2 = Mixed/ambiguous results
XNo, known not to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
No data found
?Possibly, status not identified
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
Yes, known to cause a problem
No data found
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
Possible immune system and blood toxicant
May cause stomatitis, nausea, vomiting and adbominal pain
Handling issues
Property
Value and interpretation
General
IMDG Transport Code is usually 6.1
CLP classification 2013
-
WHO Classification
None - not a ppp
UN Number
2811
Waste disposal & packaging
Packaging Group III (minor danger)
TRANSLATIONS
Language
Name
English
levamisole
French
-
German
-
Danish
-
Italian
-
Spanish
levamisol
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 24/06/2022
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