oxolinic acid
** dioxacin ** Translations

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Further data may be found in the VSDB

GENERAL INFORMATION

Description: An antibacterial drug used to treat urinary tract and other infections. Also shows activity against plant-pathogenic bacteria

Introduction: 1989, first introduced Japan

EC Directive 1107/2009 (repealing 91/414):
Status Not applicable
Dossier rapporteur/co-rapporteur Not applicable
Date inclusion expires Not applicable

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

General status:
Pesticide type Veterinary treatment; Fungicide
Substance group Quinolone
Substance origin Synthetic
Mode of action Works via two routes, by inhibiting the enzyme DNA gyrase and also acts as a dopamine reuptake inhibitor.
CAS RN 14698-29-4
EC number 238-750-8
CIPAC number -
US EPA chemical code -
Chemical formula C13H11NO5
SMILES c12c(cc3OCOc3c2)c(c(C(O)=O)cn1CC)=O
International Chemical Identifier (InChI) InChI=1/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)
Structure diagram/image available? Yes
Molecular mass (g mol-1) 261.23
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
Herbicide Resistance Classification (HRAC) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Physical state White to pale yellow crystalline solid
Related substances & organisms

Formulations:
Property Value
Example manufacturers of products using this active -
Example products using this active
  • Starner 20% WP
UK LERAP status Not applicable
Formulation and application details Usually administered orally in feed, drinking water or as a bolus for animal health applications or as a spray for plant pathogenic uses.


ENVIRONMENTAL FATE

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 3.2 V3 Low
Solubility - In organic solvents at 20oC (mg l-1) 10000 Q3 - Hexane -
10000 Q3 - Xylene -
10000 Q3 - Methaol -
Melting Point (oC) 315 Q3 -
Boiling Point (oC) - - -
Degradation point (oC) - - -
Flashpoint (oC) - - -
Octanol-water partition coefficient at pH 7, 20oC P 4.68 X 1001 Calculated -
Log P 1.67 R4 Low
Bulk density (g ml-1)/Specific gravity 1.55 Q3 -
Dissociation constant (pKa) at 25oC - 6. - -
Note: R3
Vapour pressure at 25oC (mPa) 0.147 Q3 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) - - -
Henry's law constant at 20oC (dimensionless) 4.93 X 10-06 Calculated Moderately volatile
GUS leaching potential index - - -
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Value - - -
Note -
Potential for particle bound transport index - - -
Maximum UV-vis absorption L mol-1 cm-1 - - -
Surface tension (mN m-1) - - -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 550 R3 Very persistent
DT50 (lab at 20oC) - - -
DT50 (field) - - -
DT90 (lab at 20oC) - - -
DT90 (field) - - -
Note Data for superficial sediments DT50 150-1000 days, various sediment depths
Aqueous photolysis DT50 (days) at pH 7 Value - - -
Note 88% degraded after 9 days
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value - R4 -
Note -
Water-Sediment DT50 (days) - - -
Water phase only DT50 (days) - - -

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity -

Other known metabolites:
Metabolite name and reference Aliases Formation Medium / Rate Estimated Maximum Occurrence Fraction Metabolising Enzymes
1-ethyl-1,4-dihydro-7-hydroxy-6-methoxy-6-oxoquinoline-3-carboxylic acid - Rat, Rabbit, Dog - -
Oxolinoyl-beta-D-glucuronic acid
Note: Active metabolite 		- Rat (Uriinary), Rabbit (Urinary), Dog (Urinary) - -
5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo-[4,5,g]quinoline-7-carboxylic acid - Human - -
- - - - -


ECOTOXICOLOGY

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF - - -
CT50 (days) - -
Bioaccumulation potential - Calculated Low
Mammals - Acute oral LD50 (mg kg-1) > 525 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) - - -
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) - - -
Fish - Chronic 21 day NOEC (mg l-1) - - -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 4.6 R4 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.38 R4 Daphnia magna -
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 Selenastrum capricornutum Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees - Acute 48 hour LD50 (µg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) - - -
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50product ha
EC50product ha
NOECproduct ha
% Effect 		- - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect - - -
Other arthropod (2) LR50 g ha-1 - - -
% Effect - - -
Soil micro-organisms - - -
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

General:
Property Value Source/Quality Score/Other Information Interpretation
Mammals - Acute oral LD50 (mg kg-1) > 525 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 Q3 Rat -
Mammals - Inhalation LC50 (mg l-1) - - -
Other Mammal toxicity endpoints Intravenous LD50 = 177 mg kg-1 V3 Mice -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) - - -
ARfD - Acute Reference Dose (mg kg-1bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) - - -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public -
Occupational -
Examples of European MRLs (mg kg-1) Value -
Note For the EU pesticides database click here
Drinking Water MAC (µg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

-

-

General human health issues [Harmfull if swallowed], [May cause visual disturbances, fever, anorexia, urticaria, and photosensitivity reactions], [May cause gastrointestinal tract problems]

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General [Corrosive]
EC Risk Classification [Xn - Harmful: R22, R34], [Xi - Irritant: R36, R37, R38]
EC Safety Classification -
WHO Classification None - not a ppp - -
US EPA Classification (formulation) - - -
UN Number -
Waste disposal & packaging -


TRANSLATIONS

Language Name
English oxolinic acid
French acide oxolinique
German -
Danish -
Italian -
Spanish acido oxolinico
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -
Record last updated: Monday 26 December 2011
Contact: aeru@herts.ac.uk