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Details

Stereochemistry ACHIRAL
Molecular Formula C13H11NO5
Molecular Weight 261.2301
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXOLINIC ACID

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1C=C3OCOC3=C2

InChI

InChIKey=KYGZCKSPAKDVKC-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C13H11NO5
Molecular Weight 261.2301
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Oxolinic acid is a synthetic quinolone antibiotic related to nalidixic acid. It is authorized in veterinary medicine for use in finfish, calves, pigs, and poultry. It acts by inhibiting bacterial type II topoisomerase activity. Oxolinic acid has been used in human medicine in several countries in the past. Its use in human medicine has largely been replaced by the fluoroquinolone antibiotics.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
3.6 μg/mL
750 mg 2 times / day multiple, oral
OXOLINIC ACID plasma
Salmo salar

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
750 mg 2 times / day multiple, oral
OXOLINIC ACID plasma
Salmo salar

Funbound

ValueDoseCo-administeredAnalytePopulation
19%
750 mg 2 times / day multiple, oral
OXOLINIC ACID plasma
Salmo salar

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended doses are for fin fish: 12 mg/kg bw/day for up to 7 days; for pigs and poultry: 20 mg/kg bw/day for up to 5 days and for calves: 20 mg/kg bw/day for up to 10 days.
Route of Administration: Oral
In Vitro Use Guide
In a synaptosomal fraction prepared from striatum of rats, oxolinic acid inhibited the [3H]dopamine uptake with an IC50=4.3+/-0.6×10^-6 M.
Substance Class Chemical
Record UNII
L0A22B22FT
Record Status Validated (UNII)
Record Version