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Tylosin
Last updated: 24/02/2024
(Also known as: tylosin A)

GENERAL INFORMATION
Description
A macrolide broad spectrum natural antibiotic licensed for use in livestock
Availability status
Current
Introduction & key dates
1961, early use record
Examples of veterinary uses
Used for the treatment of various infections e.g. pneumonia, foot rot and shipping fever in cattle. Banned in EU as growth promotor; Not approved as a feed additive in EU
Examples of species treated
Cattle; Pigs; Poultry
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved
EU Regulatory approval status
Approved
Chemical structure
Isomerism
Isomeric
Chemical formula
C₄₆H₇₇NO₁₇
Canonical SMILES
CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC
Isomeric SMILES
CC[C@@H]1C(/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H](C([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)\C)COC4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
International Chemical Identifier key (InChIKey)
WBPYTXDJUQJLPQ-TZNGNTBMSA-N
International Chemical Identifier (InChI)
InChI=1S/C46H77NO17/c1-13-33-30(22-58-45-42(57-12)41(56-11)37(52)26(5)60-45)18-23(2)14-15-31(49)24(3)19-29(16-17-48)39(25(4)32(50)20-34(51)62-33)64-44-38(53)36(47(9)10)40(27(6)61-44)63-35-21-46(8,55)43(54)28(7)59-35/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3/b15-14+,23-18+/t24-,25+,26-,27-,28+,29+,30-,32-,33-,35+,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46-/m1/s1
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Antibiotic, Antibacterial, Feed additive, Growth promotor
Substance groups
Macrolide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Natural
Mode of action
Inhibits bacterial protein synthesis
Molecular targets
[50S ribosomal protein L10, Antagonist]
CAS RN
1401-69-0
EC number
215-754-8
CIPAC number
-
US EPA chemical code
-
PubChem CID
5280440
Therapeutic Class
Antiinfectants for systemic use: Antibacterials for systemic use, Antibacterials for intramammary use
ATCvet Code
QJ01FA90; QJ51FA90
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: All food producing species)
Molecular mass
916.10
PIN (Preferred Identification Name)
-
IUPAC name
2-[(4R,6S,7R,9R,11E,13E,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
CAS name
-
Other status information
Possible groundwater contaminant
Relevant Environmental Water Quality Standards
-
Physical state
White or off-white coloured powder
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Bilosin 200 mg/ml injection Bimeda Chemicals Ltd UK National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Pharmasin Granules for drinking water Huvepharma N.V. GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Tylan Solution for Injection Elanco Europe Ltd UK National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Tylucyl Solution for Injection Vetoquinol UK Ltd GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details
Usually formulated as a solution for injection or as granules for use as a drinking water additive
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
5000
R4 R = Peer reviewed scientific publications
4 = Verified data
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
130
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.57 X 1003 Calculated -
Log P
3.41
R4 R = Peer reviewed scientific publications
4 = Verified data
High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
13.0
R4 R = Peer reviewed scientific publications
4 = Verified data
-
-
Vapour pressure at 20 °C (mPa)
2.63 X 10-29
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
2.0 X 10-26
R4 R = Peer reviewed scientific publications
4 = Verified data
Non-volatile
Volatilisation as max % of applied dose lost
From plant surface
- - -
From soil surface
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
UV max: approx 282nm
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
-
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Environmental release
Monitoring studies have identified this substance in livestock slurries
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
96
R4 R = Peer reviewed scientific publications
4 = Verified data
Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
General literature varies: DT₅₀ >5 days to 95-97 days
Manure DT₅₀ (days)
5.0
R4 R = Peer reviewed scientific publications
4 = Verified data
DT₅₀ 4.2 days in slurry/sand & 5.7 days slurry/sandy loam;
-
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)
- - -
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)
52.4
R4 R = Peer reviewed scientific publications
4 = Verified data
Slightly mobile
Koc (mL g⁻¹)
3744
Notes and range
Literatue data: Kd range 8.3-128 mL g⁻¹, Koc values range 553-7988 mL g⁻¹, soils=4
Freundlich
Kf (mL g⁻¹)
4.4
R4 R = Peer reviewed scientific publications
4 = Verified data
Moderately mobile
Kfoc (mL g⁻¹)
323.7
1/n
1.15
Notes and range
Literatue data: Kf range 2.3-7.0 mL g⁻¹, Kfoc range 153.3-518.2 mL g⁻¹, 1/n range 1.06-1.20, soils=4
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
2.95 Calculated High leachability
Bio-concentration factor
BCF (l kg⁻¹)
4
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Low potential
CT₅₀ (days)
Not available -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
dihydrodesmycosin - Animal -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
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)
> 2122
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Gallus domesticus
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
4710 mg kg feed⁻¹
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Colinus virginianus
-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
4530
R4 R = Peer reviewed scientific publications
4 = Verified data
Aporrectodea caliginosa
Low
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)
483
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna
Low
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
90
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna
Low
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)
45.0
R4 R = Peer reviewed scientific publications
4 = Verified data
Lemna gibba NOEC 7 day
Low
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
1.38
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Pseudokirchneriella subcapitata
Moderate
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)
> 5000
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
Intraperitoneal LD₅₀ = 600 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat
-
Intravenous LD₅₀ = 600 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
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
Occupational exposure may occur through inhalation and dermal contact
Mammalian dose elimination route and rate
Excreted rapidly in urine. Also found in milk
R3 R = Peer reviewed scientific publications
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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
XNo, known not to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
?Possibly, status not identified
No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
No data found  
General human health issues
May cause diarrhoea and gastrointestinal disturbance
Handling issues
Property
Value and interpretation
General
When heated to decomposition it emits toxic fumes of nitrogen oxide
CLP classification 2013
-
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
tylosin
French
tylosine
German
-
Danish
-
Italian
-
Spanish
tilosina
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-

Record last updated: 24/02/2024
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