Oxytetracycline	Last updated: 31/07/2024
(Also known as: terramycin; oxytracyl; oxytetrin; terramitsin; oxitetracycline; crop antibiotic; liquamycin)

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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	1974, first registered USA
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
Other bioactivity & uses	Antimicrobial
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	copper sulphate

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)		-	-	-
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
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. Monitoring studies have identified this substance in livestock manures.

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)		-	-	-
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)	-	-	-
	Koc (mL g⁻¹)	-
	Notes and range	-
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		-	-	-
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)		7200	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 Mouse	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)		> 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	-	-	-
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)		7200	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 Mouse	Low
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	-

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Record last updated:	31/07/2024
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