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Oxolinic acid
Last updated: 11/01/2024
(Also known as: dioxacin; crop antibiotic)
GENERAL INFORMATION
Description
A synthetic fluoroquinolone antibacterial veterinary drug active against gram-negative bacteria
Availability status
-
Introduction & key dates
1989, first introduced Japan
Examples of veterinary uses
Used to treat urinary tract and other infections
Examples of species treated
Fish; Cattle; Pigs; Poultry; Shrimps; Turtles
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
None
Chemical formula
C₁₃H₁₁NO₅
Canonical SMILES
CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
KYGZCKSPAKDVKC-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
oxolinic acid -
General status
Veterinary substance type
Antibiotic, Antibacterial, Antimicrobial, Antifungal, Medicinal drug
Substance groups
Quinolone compound
Minimum active substance purity
>98%
Known relevant impurities
8-hydroxy-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid, ethyl 5-ethyl-8-oxo-5,8-dihydro-1,3-ioxolo(4,5-gquinoline-7-carboxylate, 5-methyl-8-oxo-5,8-dihydro-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid
Substance origin
Synthetic
Mode of action
Works via two routes, by inhibiting the enzyme DNA gyrase and also acts as a dopamine reuptake inhibitor.
Molecular targets
[DNA gyrase subunit A, Antagonist]
CAS RN
14698-29-4
EC number
238-750-8
CIPAC number
None allocated
US EPA chemical code
-
PubChem CID
-
CLP index number
No data found
Therapeutic Class
Antiinfectants for systemic use: Antibacterials for systemic use
ATCvet Code
QJ01MB05
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: All food producing species)
Molecular mass
261.23
PIN (Preferred Identification Name)
-
IUPAC name
5-ethyl- 8-oxo- 5,8-dihydro [1,3] dioxolo [4,5-g] quinoline- 7-carboxylic acid
CAS name
5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid
Other status information
Annex 1 EC Reg. 2377/90
Relevant Environmental Water Quality Standards
-
Physical state
White to pale yellow crystalline solid
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
- - - -
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
3.2
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
10000
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Hexane		 -
10000
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Xylene		 -
10000
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Methanol		 -
Melting point (°C)
315
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
4.68 X 1001 Calculated -
Log P
1.67
R4 R = Peer reviewed scientific publications
4 = Verified data
 Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.55
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
6.3
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
 -
-
Vapour pressure at 20 °C (mPa)
0.147
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable
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
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
550
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
 Very persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
Data for superficial sediments DT₅₀ 150-1000 days, various sediment depths
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
88% degraded after 9 days
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
-
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
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)
-
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
 Slightly mobile
Koc (mL g⁻¹)
2260
Notes and range
Literature range for Koc is 14 to 4510
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
1.77 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Oxolinoyl-beta-D-glucuronic acid
Note: Biologically active		 - Rat (Uriinary); Rabbit (Urine); Dog (Urinary) -
5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo-[4,5,g]quinoline-7-carboxylic acid - Human -
1-ethyl-1,4-dihydro-7-hydroxy-6-methoxy-6-oxoquinoline-3-carboxylic acid - Rat; Rabbit; Dog -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 525
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
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)
> 2000
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Colinus virginianus		 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)
> 1000
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Eisenia foetida		 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)
> 20
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
 Moderate
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)
> 10
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Cyprinus carpio		 Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
35.0
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Oncorhynchus mykiss 29 day		 Low
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
4.6
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna		 Moderate
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.38
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna		 Moderate
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)
16
R4 R = Peer reviewed scientific publications
4 = Verified data
Selenastrum capricornutum		 Low
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)
> 525
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
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
1.7
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Rat		 -
Other Mammal toxicity endpoints
Intravenous LD₅₀ = 177 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Mouse		 -
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
Metabolised and excreted as metabolites in urine and faeces
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
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
No data found No data found
✓Yes, known to cause a problem
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
✓Yes, known to cause a problem
  
General human health issues
Harmfull if swallowed
May cause visual disturbances, fever, anorexia, urticaria, and photosensitivity reactions
May cause gastrointestinal tract problems
CNS toxicant
May damage vital organs
Handling issues
Property
Value and interpretation
General
Corrosive
Not explosive
Not expected to auto-ignite; Not highly flammable
CLP classification 2013
Health: H302, H371
Environment: H411
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
oxolinic acid
French
acide oxolinique
German
-
Danish
-
Italian
-
Spanish
acido oxolinico
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 11/01/2024
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