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Details

Stereochemistry ACHIRAL
Molecular Formula C13H11NO5
Molecular Weight 261.2306
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXOLINIC ACID

SMILES

CCn1cc(c(=O)c2cc3c(cc21)OCO3)C(=O)O

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 261.2306
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Its use in human medicine has largely been replaced by the fluoroquinolone antibiotics.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07065
Gene ID: 1258768.0
Gene Symbol: 52.0
Target Organism: Enterobacteria phage T4 (Bacteriophage T4)
Conditions

Conditions

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.6 μg/mL
750 mg 2 times / day multiple, oral
dose: 750 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
OXOLINIC ACID plasma
Salmo salar
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
750 mg 2 times / day multiple, oral
dose: 750 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
OXOLINIC ACID plasma
Salmo salar
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
19%
750 mg 2 times / day multiple, oral
dose: 750 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
OXOLINIC ACID plasma
Salmo salar
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
750 mg 2 times / day multiple, oral
Dose: 750 mg, 2 times / day
Route: oral
Route: multiple
Dose: 750 mg, 2 times / day
Sources:
unhealthy, 35.7 years (range: 16- 77 years)
n = 30
Health Status: unhealthy
Condition: urinary tract infection
Age Group: 35.7 years (range: 16- 77 years)
Sex: M+F
Population Size: 30
Sources:
Disc. AE: Insomnia, Nausea...
AEs leading to
discontinuation/dose reduction:
Insomnia (1 patient)
Nausea (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Insomnia 1 patient
Disc. AE
750 mg 2 times / day multiple, oral
Dose: 750 mg, 2 times / day
Route: oral
Route: multiple
Dose: 750 mg, 2 times / day
Sources:
unhealthy, 35.7 years (range: 16- 77 years)
n = 30
Health Status: unhealthy
Condition: urinary tract infection
Age Group: 35.7 years (range: 16- 77 years)
Sex: M+F
Population Size: 30
Sources:
Nausea 1 patient
Disc. AE
750 mg 2 times / day multiple, oral
Dose: 750 mg, 2 times / day
Route: oral
Route: multiple
Dose: 750 mg, 2 times / day
Sources:
unhealthy, 35.7 years (range: 16- 77 years)
n = 30
Health Status: unhealthy
Condition: urinary tract infection
Age Group: 35.7 years (range: 16- 77 years)
Sex: M+F
Population Size: 30
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids.
1978 May
Anti-Mycobacterium avium activity of quinolones: in vitro activities.
1993 Sep
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000 Oct
Patents

Sample Use Guides

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
Created
by admin
on Fri Jun 25 21:13:42 UTC 2021
Edited
by admin
on Fri Jun 25 21:13:42 UTC 2021
Record UNII
L0A22B22FT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXOLINIC ACID
EP   HSDB   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
W-4565
Code English
OXOLINIC ACID [HSDB]
Common Name English
5-ETHYL-5,8-DIHYDRO-8-OXO-1,3-DIOXOLO(4,5-G)QUINOLINE-7-CARBOXYLIC ACID
Systematic Name English
OXOLINIC ACID [MART.]
Common Name English
NSC-110364
Code English
OXOLINIC ACID [MI]
Common Name English
AQUALINIC
Brand Name English
OXOLINATE
Common Name English
OXOLINIC ACID [INN]
Common Name English
5-ETHYL-5,8-DIHYDRO-8-OXO(1,3)DIOXOLO(4,5-G)QUINOLINE-7-CARBOXYLIC ACID
Systematic Name English
W 4565
Code English
OXOLINIC ACID [WHO-DD]
Common Name English
UTIBID
Brand Name English
OXOLINIC ACID [USAN]
Common Name English
1,3-DIOXOLO(4,5-G)QUINOLINE-7-CARBOXYLIC ACID, 5-ETHYL-5,8-DIHYDRO-8-OXO-
Common Name English
OXOLINIC ACID [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
WHO-ATC J01MB05
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
NCI_THESAURUS C795
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
WHO-VATC QJ01MB05
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
Code System Code Type Description
HSDB
3243
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
PUBCHEM
4628
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
WIKIPEDIA
OXOLINIC ACID
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
EVMPD
SUB09548MIG
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL416755
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
DRUG BANK
DB13627
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
EPA CompTox
14698-29-4
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
NCI_THESAURUS
C76921
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
INN
1866
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
DRUG CENTRAL
2024
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
RXCUI
7798
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M8314
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY Merck Index
MESH
D010093
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
FDA UNII
L0A22B22FT
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
CAS
14698-29-4
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
ECHA (EC/EINECS)
238-750-8
Created by admin on Fri Jun 25 21:13:42 UTC 2021 , Edited by admin on Fri Jun 25 21:13:42 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY