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 Its use in human medicine has largely been replaced by the fluoroquinolone antibiotics.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

1975
63
Targets

Targets

Primary TargetPharmacologyConditionPotency
DNA topoisomerase medium subunit
2
Target ID: P07065
Gene ID: 1258768.0
Gene Symbol: 52.0
Target Organism: Enterobacteria phage T4 (Bacteriophage T4)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.6 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/384788/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/384788/
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%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/384788/
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:
https://pubmed.ncbi.nlm.nih.gov/4616804
unhealthy, 35.7 years (range: 16- 77 years)
Health Status: unhealthy
Age Group: 35.7 years (range: 16- 77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4616804
Disc. AE: Insomnia, Nausea...
AEs leading to
discontinuation/dose reduction:
Insomnia (1 patient)
Nausea (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4616804
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:
https://pubmed.ncbi.nlm.nih.gov/4616804
unhealthy, 35.7 years (range: 16- 77 years)
Health Status: unhealthy
Age Group: 35.7 years (range: 16- 77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4616804
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:
https://pubmed.ncbi.nlm.nih.gov/4616804
unhealthy, 35.7 years (range: 16- 77 years)
Health Status: unhealthy
Age Group: 35.7 years (range: 16- 77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4616804
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A
26
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A
26
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:138856
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:138856
ChemicalBook
CB8177186
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8177186
eMolecules
474328
https://www.emolecules.com/cgi-bin/more?vid=474328
MolPort
MolPort-000-885-505
https://www.molport.com/shop/molecule-link/MolPort-000-885-505
ZINC
ZINC000000001875
http://zinc15.docking.org/substances/ZINC000000001875
PubMed

PubMed

TitleDatePubMed
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004-04
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000-10
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000-10
Anti-Mycobacterium avium activity of quinolones: in vitro activities.
1993-09
[Drug-induced urolithiasis caused by N4-acetylsulfamethoxazole (Biseptol) and oxolinic acid (Desurol)].
1992-11
Assessment of temafloxacin neurotoxicity in rodents.
1991-12-30
The proconvulsive activity of quinolone antibiotics in an animal model.
1991-09
The calcium entry blockers: anti-manic drugs?
1986
Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids.
1978-05
Patents

Patents

JP2011201857A
12
JP2011509971A
151
JPH05310572A
2
JPH0717810A
2
JPS62273917A
2
US3287458
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Veterinary drug.
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 Mon Mar 31 21:36:11 GMT 2025
Edited
by admin
on Mon Mar 31 21:36:11 GMT 2025
Record UNII
L0A22B22FT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AQUALINIC
Preferred Name English
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
Oxolinic acid [WHO-DD]
Common 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
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 Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
NCI_THESAURUS C795
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
WHO-VATC QJ01MB05
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
Code System Code Type Description
ALANWOOD
oxolinic acid
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
DAILYMED
L0A22B22FT
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
CHEBI
138856
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PRIMARY
HSDB
3243
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PRIMARY
PUBCHEM
4628
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
WIKIPEDIA
OXOLINIC ACID
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
EVMPD
SUB09548MIG
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL416755
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PRIMARY
DRUG BANK
DB13627
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PRIMARY
EPA CompTox
DTXSID1021089
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PRIMARY
NSC
110364
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PRIMARY
NCI_THESAURUS
C76921
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PRIMARY
INN
1866
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PRIMARY
DRUG CENTRAL
2024
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PRIMARY
RXCUI
7798
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m8314
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PRIMARY Merck Index
MESH
D010093
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PRIMARY
FDA UNII
L0A22B22FT
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
CAS
14698-29-4
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
SMS_ID
100000083072
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PRIMARY
ECHA (EC/EINECS)
238-750-8
Created by admin on Mon Mar 31 21:36:11 GMT 2025 , Edited by admin on Mon Mar 31 21:36:11 GMT 2025
PRIMARY
Related Record Type Details
Structure of SODIUM OXOLINATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of OXOLINIC ACID
ACTIVE MOIETY
NIH
NCATS
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