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Oxytetracycline
Last updated: 07/03/2024
(Also known as: terramycin; oxytracyl; oxytetrin; terramitsin; oxitetracycline; crop antibiotic; liquamycin)

GENERAL INFORMATION
Description
A highly active broad spectrum antibiotic used to control infection animals diseses and bacterial pathogens. Usually used as the hydrochloride salt.
Availability status
Current
Introduction & key dates
-
Examples of veterinary uses
Used to control gastrointestinal and respiratory diseases as well as some skin conditions including Rickettsial infections, Lupus
Examples of species treated
Calves; Non-lactating dairy cattle; Beef; Pigs; Fish; Poultry; Cats; Dogs
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved
EU Regulatory approval status
Approved
Chemical structure
Isomerism
A complex molecule with 6 chiral centres
Chemical formula
C₂₂H₂₄N₂O₉
Canonical SMILES
CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O
Isomeric SMILES
C[C@@]1([C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O
International Chemical Identifier key (InChIKey)
IWVCMVBTMGNXQD-PXOLEDIWSA-N
International Chemical Identifier (InChI)
InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
oxytetracycline -
General status
Veterinary substance type
Bactericide, Antimicrobial, Antiseptic, Medicated feed additive
Substance groups
Micro-organism derived substance
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Natural
Mode of action
Broad spectrum, protein synthesis inhibitor and binds to the 30S and 50S bacterial ribosomal subunits
Molecular targets
[30S ribosomal protein S9, Antagonist], [30S ribosomal protein S4, Antagonist], [16S rRNA, Antagonist]
CAS RN
79-57-2
Alternative/old CAS RN
2058-46-0; 6153-64-6 (dihydrate)
EC number
201-212-8
CIPAC number
316
US EPA chemical code
006308
PubChem CID
-
Therapeutic Class
Dermatologicals: Antibiotics and chemotherapeutics for dermatological use; Antiinfectants for systemic use: Antibacterials for systemic use
ATCvet Code
QD06AA03 for topical use; QJ01AA06 for systemic use; Others available
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: All food producing species)
Molecular mass
460.44
PIN (Preferred Identification Name)
-
IUPAC name
(4S,4aR,5S,5aR,6S,12aS)-4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxonaphthacene-2-carboxamide
CAS name
(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
Other status information
Possible groundwater contaminant
Relevant Environmental Water Quality Standards
-
Physical state
Pale yellow to tan coloured crystalline powder
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Alamycin Solution for Injection Norbrook Laboratories Ltd UK National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Engemycin DD Solution for Injection MSD Animal Health UK Ltd UK National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Hypersol Powder for Drinking Water Huvepharma SA GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Cyclosol LA 200mg/ml Solution for Injection Eurovet Animal Health B.V. GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details
Currently available formulations include solutions for injection, cutaneous sprays, powders for adding to drinking water and medicated premix feeds
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
600
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
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
Decomposes on melting
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)
179
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
-
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
- - -
Log P
- - -
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
- - -
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)
- - -
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)
43.8
R4 R = Peer reviewed scientific publications
4 = Verified data
Aerobic sediment slurry; Other data DT₅₀ (1) 79 days slurry; (2) 12,0-15.4 day slurry
-
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
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
Bio-concentration factor
BCF (l kg⁻¹)
0.6
J2 J = Pesticide Action Network database (click here )
2 = Unverified data of unknown source
Mollusca
Low potential
CT₅₀ (days)
Not available -
Known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
- - -
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)
> 5620
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
Anas platyrhynchos as HCl variant
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
1954
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
as HCl variant
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)
100
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
as HCl variant
Moderate
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)
116
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
Oncorhynchus mykiss as HCl variant
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)
102
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
Daphnia magna as HCl variant
Low
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
46.2
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Daphnia magna as HCl variant
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)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
0.342
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Selenastrum capricornutum as HCl variant
Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
0.183
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Selenastrum capricornutum as HCl variant
Moderate
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)
- - -
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
Systemically available oxytetracycline was primarily excreted in the urine and bile
Q3 Q = Miscellaneous data from online sources
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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
Yes, known to cause a problem
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
XNo, known not to cause a problem
Yes, known to cause a problem
Yes, known to cause a problem
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
May cause hypersensitivity reactions
May cause tooth discoloration
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H302, H312, H317, H332, H360d
Environment: H400, H410
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
oxytetracycline
French
oxytetracycline
German
Oxytetracyclin
Danish
oxytetracyclin
Italian
oxytetracicline
Spanish
oxitetraciclina
Greek
-
Polish
oksytetracyklina
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-

Record last updated: 07/03/2024
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