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

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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	tylosin tartrate tylosin phosphate

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 – Acute EC₅₀ development (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)		> 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	-

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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