Ceftiofur

Ceftiofur	Last updated: 31/05/2024
(Not known by any other names)

GENERAL INFORMATION

Description

Broad spectrum third generation cephalosporin drug used to treat bacterial infections of the respiratory tract. It is often formulated using the hydrochloride salt.

Availability status

Current

Introduction & key dates

1987, first described

Examples of veterinary uses

Typically used to treat bovine respiratory disease caused by Pasteurella spp. and for urinary tract infections in dogs

Examples of species treated

Cattle; Pigs; Horses; Goats; Chickens; Turkeys

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Isomeric

Chemical formula

C₁₉H₁₇N₅O₇S₃

Canonical SMILES

CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)O

Isomeric SMILES

CO/N=C(\C1=CSC(=N1)N)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)O

International Chemical Identifier key (InChIKey)

ZBHXIWJRIFEVQY-IHMPYVIRSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-/t12-,16-/m1/s1

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Antibacterial, Antibiotic, Medicinal drug

Substance groups

Cephalosporin

Minimum active substance purity

Known relevant impurities

Substance origin

Semi-synthetic

Mode of action

Inhibition of the bacteria cell wall synthesis

Molecular targets

[Beta-lactamase, Agonist]

CAS RN

80370-57-6

EC number

CIPAC number

US EPA chemical code

PubChem CID

6328657

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for systemic use, Antibacterials for intramammary use

ATCvet Code

QJ01DD90; QJ51DA91

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: All mammalian food producing species)

Molecular mass

523.56

PIN (Preferred Identification Name)

IUPAC name

(6R,7R)-7-[ [(2Z)-2-(2-amino-1,3-thiazol-4-yl)- 2-methoxyiminoacetyl]amino]-3-(furan-2- carbonylsulfanylmethyl)-8-oxo-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CAS name

3-[(2-furylcarbonyl)thio]methyl]-7-[2-(2-amino-4-thiazolyl)-2- (methoxyiminoacetamido)-3-cephem-4-carboxylic acid

Other status information

Relevant Environmental Water Quality Standards

Physical state

Solid

Related substances & organisms

ceftiofur hydrochloride

ceftiofur sodium

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Formulation and application details

Usually formulated, using the hydrochloride salt, as a solution for injection

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

249

Moderate

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

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

3.47 X 10⁰⁰

Calculated

Log P

0.54

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

2.62

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

Absorb at wavelengths >290nm

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Environmental release may occur via direct deposition of faeces and urine in the field from treated animals or via the spreading of manures and slurry.

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

37.5

Moderately persistent

DT₅₀ (lab at 20 °C)

37.5

Moderately persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

General literature values: in clay loam at pH 5 DT₅₀ 22.2 days; sand at pH 7 DT₅₀ 49 days; silty clay loam at pH 9 DT₅₀ 41.1 days; Other studies DT₅₀ range 0.76-4.31 days

Manure DT₅₀ (days)

1.0

In poultry litter DT₅₀ for ceftiofur was 25 hours; Other data DT₅₀ 1.7-41 days

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)

Sediment 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)

Slightly mobile

K_oc (mL g⁻¹)

3700

Notes and range

Estimated

Freundlich

K_f (mL g⁻¹)

90.0

K_foc (mL g⁻¹)

¹/_n

Notes and range

Literature data K_f range 57.63-122.44 μg l⁻¹

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.68

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

3.0

Low potential

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

desfuroylceftiofur

DFC

Rat (Urine)

ceftiofur sulfoxide

Rat (Urine)

desfuroylceftiofur

Cattle

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 7760

Rat

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)

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

Notes

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)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

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 (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)

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

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)

> 7760

Rat

Low

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 8.3

Rat 4 hr

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

May occur through dermal contact

Mammalian dose elimination route and rate

Rapidly metabolised and eliminated, 60-80% with urine, remainder in faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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

May cause diarrhoea, colitis, depression in body-weight gain and in serum glucose, and acidification of urine

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

Shelf-life as packaged for sale: 3 years. Store in a refrigerator (2ºC - 8ºC) and protect from light.

TRANSLATIONS

Language

Name

English

ceftiofur

French

German

Danish

Italian

Spanish

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Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	31/05/2024
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