Tetracycline	Last updated: 02/05/2024
(Also known as: omegamycin ; abramycin ; anhydrotetracycline)

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GENERAL INFORMATION

Description	Broad spectrum antibiotic compound synthesised or derived from certain microorganisms of the genus Streptomyces used in veterinary products and for aquaculture
Availability status	Current
Introduction & key dates	-
Examples of veterinary uses	Used to treat certain bacterial infections and inflammatory skin conditions
Examples of species treated	Pigs; Chickens; Cattle; Poultry; Fish; Sheep

Approval status

VMR 2013/2033 approval status (GB/UK)	Approved
EU Regulatory approval status	Approved

Chemical structure

Isomerism	Isomeric
Chemical formula	C₂₂H₂₄N₂O₈
Canonical SMILES	CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
Isomeric SMILES	C[C@@]1([C@H]2C[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
International Chemical Identifier key (InChIKey)	OFVLGDICTFRJMM-WESIUVDSSA-N
International Chemical Identifier (InChI)	InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
2D structure diagram/image available?	Yes

General status

Veterinary substance type	Antimicrobial, Feed additive
Substance groups	Tetracycline substance
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Natural
Mode of action	Protein synthesis inhibitor
Molecular targets	[30S ribosomal protein S7, Antagonist], [30S ribosomal protein S14, Antagonist], [30S ribosomal protein S3, Antagonist], [30S ribosomal protein S8, Antagonist], [30S ribosomal protein S19, Antagonist], [16S rRNA, anatogonist], [Major prion protein, Antagonist]
CAS RN	60-54-8
EC number	200-481-9
CIPAC number	-
US EPA chemical code	-
PubChem CID	54675776
Therapeutic Class	Antiinfectants for systemic use; Dermatologicals; Genito urinary system & sex hormones; Sensory organs
ATCvet Code	QJ01AA07;QJ51AA07; QD06AA04; QG01AA90; QG51AA02; QS01AA09; QS02AA08; QS03AA02
Controlled Drug?	No
Regulation 37/2010 MRL Classification	Allowed substance (Table 1: All food producing species)
Molecular mass	444.4
PIN (Preferred Identification Name)	-
IUPAC name	(4S,4αS,5αS,6S,12αR)-4-(dimethylamino)-1,6,10,11,12α-pentahydroxy-6-methyl-3,12-dioxo-4,4α,5,5aα-tetrahydrotetracene-2-carboxamide
CAS name	6-methyl-1,11-dioxy-2-naphthacenecarboxamide
Other status information	PAN Bad Actor chemical, Possible groundwater contaminant
Relevant Environmental Water Quality Standards	-
Physical state	Yellow crystalline solid

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)
	Animedazon Cutaneous Spray	antiMedica GmbH	GB National authorisation	Prescription only medicine to be authorised by a veterinarian (POM-V)
	Aquatet Premix Medicted feeding stuff	Pharmaq Ltd	UK National authorisation	Prescription only medicine to be authorised by a veterinarian (POM-V)
	Bovocycline Pessary IntrauterineTablet	Eurovet Animal Health B.V.	GB National authorisation	Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details	Available in a wide range of formulations including solutions for injection, cutaneous sprays, pesseries and medicated feeding stuffs

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		1700	R4 R = Peer reviewed scientific publications 4 = Verified data	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		20	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Ethanol	-
Melting point (°C)		172.5	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	5.01 X 10-02	Calculated	-
	Log P	-1.3	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source	Low
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		-	-	-
Dissociation constant pKa) at 25 °C		3.3	R4 R = Peer reviewed scientific publications 4 = Verified data	-
		pKa(2)=7.8; pKa(3)=9.6
Vapour pressure at 20 °C (mPa)		4.11 X 10-18	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)		-	-	-
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 urine 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)	30	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	Moderately persistent
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	Note	-
Manure DT₅₀ (days)		4.5	R4 R = Peer reviewed scientific publications 4 = Verified data Aerated pig manure DT₅₀ 9 days non-aerated; Other data 9-17 days in liquid manure	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	0.1	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	Fast
	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)	-	R4 R = Peer reviewed scientific publications 4 = Verified data	Non-mobile
	Koc (mL g⁻¹)	40000
	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		-0.89	Calculated	Low leachability
Bio-concentration factor	BCF (l kg⁻¹)	-	-	-
	CT₅₀ (days)	-		-

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		807	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 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)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		-	-	-
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)		260.5	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 Danio rerio 1 day	Low
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		29.4	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	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)		1.0	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 Lemna gibba	Moderate
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		2.2	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	-	-	-

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)		807	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 Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		-	-	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		-	-	-
Other Mammal toxicity endpoints		Intraperitoneal LD₅₀ = 310 mg kg⁻¹	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source rat	-
		Intravenous LD₅₀ = 129 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	-
Mammalian dose elimination route and rate		Excreted unchanged in urine and to a lesser extent, in bile. Also identified in milk.	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	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor ?Possibly, status not identified 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 ; E1 E = Unspecified genotoxicity type (miscellaneous data source) 1 = Positive No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ✓Yes, known to cause a problem XNo, known not to cause a problem No data found Respiratory tract irritant Skin irritant Skin sensitiser ✓Yes, known to cause a problem ✓Yes, known to cause a problem No data found Eye irritant Phototoxicant   ✓Yes, known to cause a problem No data found
General human health issues		May cause produce nausea, abdominal pain and burning and vomiting May cause renal dysfunction or failure Acts as co-carcinogen with UV radiation and increases the risk of skin cancer

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	-
WHO Classification	Not listed (Not listed)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	tetracycline
French	tetracycline
German	-
Danish	-
Italian	-
Spanish	tetraciclina
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	02/05/2024
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