Danofloxacin mesylate

Danofloxacin mesylate	Last updated: 06/09/2025
(Not known by any other names)

GENERAL INFORMATION

Description

A synthetic fluoroquinolone broad spectrum antibacterial and antimicrobial veterinary treatment

Examples of veterinary uses

Used to control infections of the respiratory tract and intestinal tract including bovine respiratory disease associated with Mannheimia (Pasteurella) haemolytica and Pasteurella multocida

Examples of species treated

Cattle; Pigs; Domestic fowl

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V)

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Danofloxacin mesylate exhibits stereoisomerism, specifically chirality, due to the presence of multiple chiral centres in its molecular structure. The key stereocentres are located within the diazabicyclo[2.2.1]heptane ring system and the cyclopropyl group attached to the quinolone core. These chiral centres give rise to distinct enantiomers. The biologically active form used in veterinary medicine is the (1S)-enantiomer, which has been shown to possess optimal antibacterial activity by effectively inhibiting DNA gyrase, a critical bacterial enzyme. The mesylate salt form enhances solubility and stability but does not alter the stereochemistry of the danofloxacin molecule itself.

Chemical formula

C₂₀H₂₄FN₃O₆S

Canonical SMILES

CN1CC2CC1CN2C3=C(C=C4C(=C3)N(C=C(C4=O)C(=O)O)C5CC5)F.CS(=O)(=O)O

Isomeric SMILES

CN1C[C@@H]2C[C@H]1CN2C3=C(C=C4C(=C3)N(C=C(C4=O)C(=O)O)C5CC5)F.CS(=O)(=O)O

International Chemical Identifier key (InChIKey)

APFDJSVKQNSTKF-FXMYHANSSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H20FN3O3.CH4O3S/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10;1-5(2,3)4/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26);1H3,(H,2,3,4)/t11-,12-;/m0./s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
danafoxacin dihydrate	Parent hydrate

General status

Veterinary substance type

Antibacterial, Antimicrobial

Substance groups

Fluoroquinolone

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibits DNA gyrase and triggers induction of the SOS response and temperate bacteriophages

Molecular targets

[DNA gyrase subunit A, Antagonist]

CAS RN

119478-55-6

EC number

CIPAC number

US EPA chemical code

PubChem CID

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for systemic use

ATCvet Code

QJ01MA92

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: All food producing species)

Molecular mass

453.48

PIN (Preferred Identification Name)

IUPAC name

(1S)-1-cyclopropyl-6-fluoro-1,4-dihydro-7-(5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-4-oxo-3-quinoline carboxylic acid methanesulphonate

CAS name

Forever chemical

Other status information

Relevant Environmental Water Quality Standards

Physical state

White to off-white crystalline powder

Related substances & organisms

danofloxacin

Commercial

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Availability status

Current

Introduction & key dates

Example products (past and present) using this active

Advocin 180 mg/ml Solution for Injection for Cattle

Zeotis UK Ltd

GB National authorisation

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

Advosin 2.5% solution for Injection

Zeotis UK Ltd

UK National authorisation

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

Formulation and application details

Usually formulated as a solution for injection

Commercial production

The production of danofloxacin mesylate involves a multi-step chemical synthesis beginning with the condensation of N-methyl bridged piperazine and cyclopropanecarboxylic acid in the presence of an acid-binding agent at elevated temperatures, forming the danofloxacin base. This intermediate is then dissolved in water and reacted with methanesulfonic acid to form the mesylate salt. The solution is refluxed to promote salification, followed by crystallisation and drying to yield the final danofloxacin mesylate product.

Impact on climate of production and use

Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

65.6

Moderate

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

100

Ethanol

100

Acetone

Melting point (°C)

328

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

2.45 X 10⁰⁰

Calculated

Log P

0.39

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

6.22

PKa(2)=9.43

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

pH 5: 208nm=12090, 234nm=8553, 282nm=47796, 310nm=9957, 350nm=10682
pH7: 234nm=10612, 276nm=43268, 336nm=13244
pH9: 234nm=11392, 277nm=41978, 328nm=13877

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Released intermittently into the environment via faeces and urine of medicated animals as well as via the spreading of manure

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

115

Persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Literature values DT₅₀ range 87-143 mL g⁻¹

Manure DT₅₀ (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)

2837

Non-mobile

K_oc (mL g⁻¹)

284533

Notes and range

USEPA data K_d range 2280-3800 mL g⁻¹, K_oc range 75600-644000 mL g⁻¹, Soils=3; Data for faecal adsorption; K_d range 138-541 mL g⁻¹, K_oc range 323-1036 mL g⁻¹

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

-3.00

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-desmethyldanofloxacin

Cattle

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

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)

> 1200

Lumbricus terrestris

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

Vegetative vigour ER₅₀ (g ha⁻¹)

Seedling emergence ER₅₀ (g ha⁻¹)

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)

> 100

Cyprinodon variegatus marine species

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)

> 63.5

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)

> 100

Americamysis bahia

Low

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, fonds growth, fresh) - 7 day (mg l⁻¹)

Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)

Algae - Acute (growth rate, fresh; mg l⁻¹)

Algae - Chronic (growth rate, fresh; 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)

> 2000

Rat

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

In rats, dogs and pigs it is excreted in the unchanged form in the urine

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 gastrointestinal problems

Handling issues

Property

Value and interpretation

General

Not compatible with oxidising agents
May emit hamful gases when heated

CLP classification 2013

Health: H373
Environment: H412

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

danofloxacin mesylate

French

mesilate de danofloxacine

German

Danish

Italian

mesilato de danofloxacino

Spanish

mesilato de danofloxacino

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	06/09/2025
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