Chlortetracycline hydrochloride

Chlortetracycline hydrochloride	Last updated: 24/05/2024
(Also known as: chlortetracycline HCl)

GENERAL INFORMATION

Description

Broad spectrum antibiotic and antimicrobial substance isolated from the microorganism (treptomyces aureofaciens) used in veterinary products and for aquaculture

Availability status

Current

Introduction & key dates

1945, first discovered

Examples of veterinary uses

Mainly used for the prevention of infections of superficial traumatic or surgical wounds

Examples of species treated

Agricultural livestock including: Poultry, Pigs, Cattle and Fish

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Isomeric

Chemical formula

C₂₂H₂₄Cl₂N₂O₈

Canonical SMILES

CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl

Isomeric SMILES

C[C@@]1(C2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl

International Chemical Identifier key (InChIKey)

QYAPHLRPFNSDNH-LYNLVHCPSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26-27,30,32-33H,6H2,1-3H3,(H2,24,31);1H/t7?,8-,15-,21-,22-;/m0./s1

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Medicinal drug, Bactericide, Antimicrobial, Medicated feed additive

Other bioactivity & uses

Wood preservative, Antimicrobial, Bactericide

Substance groups

Amide pesticide; Tetracycline compound

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

Protein synthesis inhibitor

Molecular targets

[16S ribosomal RNA, Inhibitor], [30S ribosomal proteins, Inhibitor], [ADP-ribosylation factor 1, Inhibitor], [Catalase, Inhibitor], [Ephrin type-B receptor 1, Inhibitor], [Pancreatic triacylglycerol lipase, Inhibitor], [Protein-arginine deiminase type-4, Inhibitor]

CAS RN

64-72-7

Alternative/old CAS RN

3671-08-7

EC number

200-591-7

CIPAC number

US EPA chemical code

006301

PubChem CID

54684459

Therapeutic Class

Dermatologicals: Antibiotics & chemotherapeutics for dermatological use

ATCvet Code

QD06AA52

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: All food producing species)

Molecular mass

515.3

PIN (Preferred Identification Name)

IUPAC name

(4S,4aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride

CAS name

Other status information

Possible groundwater contaminant

Relevant Environmental Water Quality Standards

Physical state

Related substances & organisms

chlortetracycline

chlortetracycline calcium complex

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Aurofac Granular 100mg/g premix medicated feed

Zoetis UK Ltd

UK National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Animedazon Spray

aniMedica GmbH

GB National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Chlorsol Powder

Vetoquinon UK Ltd

UK National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Ophtocycline Eye Ointment

LeVet Beheer B.V

GB National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Formulation and application details

Available in a variety of formulations including medicated premix feed, cutaneous sprays, ointments, cutaneous sprays and powders for oral administration

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

630

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

168.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

2.40 X 10^-01

Calculated

Log P

-0.62

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

4.5

Vapour pressure at 20 °C (mPa)

2.09 X 10^-23

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

4.8 X 10^-22

Non-volatile

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.

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

General literature DT₅₀ range >30 days (R3)

Manure DT₅₀ (days)

44% lost after 30 days

Soil and poultry manure at 30°C decreases with decreasing temp

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

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (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)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 1500

Mouse

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)

> 0.89

Unknown species

Moderate

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)

128

Daphnia magna

Low

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)

1.62

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

3.1

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

> 1500

Mouse

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Intraperitoneal LDLo = 335 mg kg⁻¹

Rat

Intravenous LD₅₀ = 118 mg kg⁻¹

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

Mainly eliminated in the faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

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

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English

chlortetracycline hydrochloride

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Record last updated:	24/05/2024
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