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Tilmicosin
Last updated: 20/03/2024
(Also known as: 20-deoxy-20-(3,5-dimethylpiperidin-1-yl)-desmycosin ; AH0230 / AH0470; tilmicosina)
GENERAL INFORMATION
Description
A semi-synthetic macrolide antibiotic
Availability status
Current
Introduction & key dates
-
Examples of veterinary uses
Used for the treatment and prevention of pneumonia associated with Pasteurella haemolytica, P. multocida, Actinobacillus pleuropneumoniae, mycoplasma species and other microorganisms
Examples of species treated
Cattle; Sheep; Pigs; Poultry; Rabbits; Fish
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved
EU Regulatory approval status
Approved
Chemical structure
Isomerism
Isomeric - available in both the cis- and trans-forms
Chemical formula
C₄₆H₈₀N₂O₁₃
Canonical SMILES
CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)O)N(C)C)O)CCN3CC(CC(C3)C)C)C)C)COC4C(C(C(C(O4)C)O)OC)OC
Isomeric SMILES
CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](C(CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)N(C)C)O)CCN3CC(CC(C3)C)C)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
International Chemical Identifier key (InChIKey)
JTSDBFGMPLKDCD-SWSPHLSKSA-N
International Chemical Identifier (InChI)
InChI=1S/C46H80N2O13/c1-13-36-33(24-57-46-44(56-12)43(55-11)40(53)31(8)59-46)19-25(2)14-15-34(49)28(5)20-32(16-17-48-22-26(3)18-27(4)23-48)42(29(6)35(50)21-37(51)60-36)61-45-41(54)38(47(9)10)39(52)30(7)58-45/h14-15,19,26-33,35-36,38-46,50,52-54H,13,16-18,20-24H2,1-12H3/b15-14+,25-19+/t26-,27+,28-,29+,30-,31-,32+,33-,35-,36-,38+,39-,40-,41-,42-,43-,44-,45+,46-/m1/s1
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Antibiotic, Antibacterial, Antimicrobial, Medicinal drug, Medicated feed additive
Substance groups
Macrolide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Semi-synthetic
Mode of action
Interferes with protein synthesis
Molecular targets
[50S rRNA, Antagonist]
CAS RN
108050-54-0
EC number
-
CIPAC number
-
US EPA chemical code
-
PubChem CID
5282521
Therapeutic Class
Antiinfectants for systemic use: Antibacterials for systemic use
ATCvet Code
QJ01FA91
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: All food producing species)
Molecular mass
869.15
PIN (Preferred Identification Name)
-
IUPAC name
(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-7-[2-[(3R,5S)-3,5-dimethylpiperidin-1-yl]ethyl]-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-1-oxacyclohexadeca-11,13-diene-2,10-dione
CAS name
4A-O-de(2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl)-20-deoxy-20-(3,5-dimethyl-1-piperidinyl)-(20(cis: trans)) tylosin
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
-
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Apotil Solution for Injection Nimrod Veterinary Products Ltd UK National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Hymantil solution for injection Industrial Veterinaria S.A. GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Tilmovet Oral Granules Huvepharma N.V. GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details
A wide variety of formulations are available including solutions for injection, granules and premixed medicated feeds
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
566000
R4 R = Peer reviewed scientific publications
4 = Verified data
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
107
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
1.23 X 1005 Calculated -
Log P
5.09
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
13.16
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
-
Vapour pressure at 20 °C (mPa)
- - -
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
UV max: 283nm = 22643
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 -
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Environmental release
Substance may enter the environment via the faeces of treated animals or by leaching from spilt medicated feed.
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
64
R4 R = Peer reviewed scientific publications
4 = Verified data
 Moderately persistent
DT₅₀ (lab at 20 °C)
730
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Very persistent
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
USEPA data: suggests soil DT₅₀ >2 years; Literature variable & sparse (i) 45.9% decline in loam soil after 1 year, no decline in clay loam after 1 year (E3); (ii) >64 days (R3)
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
0.82
E4 E = Manufacturers safety data sheets
4 = Verified data
 Fast
Note
Not pH sensitive
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
E4 E = Manufacturers safety data sheets
4 = Verified data
 Stable
Note
Stable at pH 5 & 7, DT₅₀ 156 days at pH 9
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)
178.5
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Non-mobile
Koc (mL g⁻¹)
16319
Notes and range
USEPA data: Kd range 86-318 mL g⁻¹, Koc range 4244-36150 mL g⁻¹, Soils=4
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
-0.61 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
450
V1 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
1 = Estimated data with little or no verification
Estimated		 Threshold for concern
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
tilmicosin sulphate - Rat -
N-desmethyl tilmicosin - Animal -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 800
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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)
> 4710 mg kg feed⁻¹
E4 E = Manufacturers safety data sheets
4 = Verified data
Anas platyrhynchos		 -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
> 918
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Eisenia foetida 28 day		 Moderate
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)
851
E4 E = Manufacturers safety data sheets
4 = Verified data
Oncorhynchus mykiss		 Low
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)
57.3
E4 E = Manufacturers safety data sheets
4 = Verified data
Daphnia magna		 Moderate
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)
0.35
E4 E = Manufacturers safety data sheets
4 = Verified data
Selenastrum capricornutum Growth		 Moderate
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)
> 800
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Rat		 Moderate
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
Very little metabolism, excreted unchanged predominately in the faeces
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
 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
Severe allergen
Cardiovascular toxicant
Handling issues
Property
Value and interpretation
General
May emit toxic fumes when heated to decomposition
CLP classification 2013
-
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
tilmicosin
French
tilmicosine
German
-
Danish
-
Italian
-
Spanish
tilmicosina
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 20/03/2024
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