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Gliotoxin (Ref: SN 12879)
Last updated: 14/09/2023
(Also known as: aspergillin; Antibiotic SN 12870)

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
   
Human health
High alert:
Mammals acute toxicity: High
Warning:
Significant data are missing
GENERAL INFORMATION
Description
An obsolete mycotoxin with a range of applications including wood preservation, antibiotic and fungicide
Example pests controlled
Wood rot
Example applications
Wood structures
Efficacy & activity
-
Appearance and life cycle
-
Availability status
Considered obsolete but may be available in some countries
Introduction & key dates
-
Taxonomic classification
-
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
Approved for use (✓) under EC 1107/2009 in the following EU Member States
ATAustria
BEBelgium
BGBulgaria
CYCyprus
CZCzech Republic
DEGermany
DKDenmark
EEEstonia
ELGreece
                 
ESSpain
FIFinland
FRFrance
HRCroatia
HUHungary
IEIreland
ITItaly
LTLithuania
LULuxembourg
                 
LVLatvia
MTMalta
NLNetherlands
PLPoland
PTPortugal
RORomania
SESweden
SISlovenia
SKSlovakia
                 
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries
ISIceland
NONorway
                 
Additional information
Known to be used in the following countries
-
Chemical structure
Isomerism
Gliotoxin is a complex molecule with 4 chiral centres.
Chemical formula
C₁₃H₁₄N₂O₄S₂
Canonical SMILES
CN1C(=O)C23CC4=CC=CC(C4N2C(=O)C1(SS3)CO)O
Isomeric SMILES
CN1C(=O)[C@]23CC4=CC=C[C@@H]([C@H]4N2C(=O)[C@]1(SS3)CO)O
International Chemical Identifier key (InChIKey)
FIVPIPIDMRVLAY-RBJBARPLSA-N
International Chemical Identifier (InChI)
InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
gliotoxin Unstated isomer
General status
Biopesticide type
Fungicide, Other substance
Other constituent type
Wood preservative
Substance groups
Micro-organism
Minimum active substance purity
>99%
Known relevant impurities
-
Substance origin
Natural
Mode of action
Various mechanisms including inhibition of chymotrypsin-like activity of the 20S proteasome, Ca2+ release from mitochondria and activation of transcription factor NF-kB in response to a variety of stimuli in T and B cells. Proteasome inhibitor.
Substance source
A potent epithiodioxopiperazine mycotoxin produced by species in the genera Gliocladium, Aspergillus and Penicillium
Substance production
-
Uses
-
Target pests
-
Target host
-
Farming system suitability
-
CAS RN
67-99-2
EC number
636-170-3
CIPAC number
-
US EPA chemical code
-
PubChem CID
6223
CLP index number
No data found
Molecular mass
326.40
PIN (Preferred Identification Name)
-
IUPAC name
(3R,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino(1,2-a)indole-1,4-dione
CAS name
-
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Class (HRAC MoA class)
Not applicable
Herbicide Resistance Class (WSSA MoA class)
Not applicable
Insecticide Resistance Class (IRAC MoA class)
Not applicable
Fungicide Resistance Class (FRAC MOA class)
BM02
Examples of recorded resistance
-
Physical state
White to pale yellow powder
Formulations
Property
Product
Manufacturer
Example products
- -
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
700
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
at 30 °C
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
1000
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Chloroform
-
Melting point (°C)
Decomposes on melting
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Boiling point (°C)
221
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
7.94 X 1002 Calculated -
Log P
2.90
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Moderate
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.75
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
- - -
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)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
- - -
Note
-
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
- - -
Koc
-
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
67
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat
High
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 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)
- - -
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)
- - -
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 - 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)
67
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat
High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
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
-
Mammalian dose elimination route and rate
- - -
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
No data found No data found No data found
Respiratory tract irritant Skin irritant Skin sensitiser
No data found No data found No data found
Eye irritant Phototoxicant  
No data found No data found  
General human health issues
Has immunosuppressive properties
Handling issues
Property
Value and interpretation
General
IMDG Transport Hazard Class 6.1
CLP classification 2013
-
WHO Classification
Not listed (Not listed)
UN Number
UN2811
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
gliotoxin
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-

Record last updated: 14/09/2023
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