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Details

Stereochemistry ACHIRAL
Molecular Formula C13H10NO5.Na
Molecular Weight 283.212
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM OXOLINATE

SMILES

[Na+].CCN1C=C(C([O-])=O)C(=O)C2=CC3=C(OCO3)C=C12

InChI

InChIKey=WANXPWCBQXXPFK-UHFFFAOYSA-M
InChI=1S/C13H11NO5.Na/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);/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula C13H10NO5
Molecular Weight 260.2222
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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 Its use in human medicine has largely been replaced by the fluoroquinolone antibiotics.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
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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)
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:
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)
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:
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)
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:
https://pubmed.ncbi.nlm.nih.gov/4616804
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A
22
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A
22
 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
MolPort
MolPort-000-885-505
https://www.molport.com/shop/molecule-link/MolPort-000-885-505
ZINC
ZINC000000001875
http://zinc15.docking.org/substances/ZINC000000001875
eMolecules
474328
https://www.emolecules.com/cgi-bin/more?vid=474328
PubMed

PubMed

TitleDatePubMed
The calcium entry blockers: anti-manic drugs?
1986
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000 Oct
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
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 Sat Dec 16 07:50:45 UTC 2023
Edited
by admin
on Sat Dec 16 07:50:45 UTC 2023
Record UNII
8O78VP5TTM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM OXOLINATE
Systematic Name English
1,3-DIOXOLO(4,5-G)QUINOLINE-7-CARBOXYLIC ACID, 5-ETHYL-5,8-DIHYDRO-8-OXO-, SODIUM SALT
Common Name English
OXOLINIC ACID SODIUM SALT
Common Name English
1,3-DIOXOLO(4,5-G)QUINOLINE-7-CARBOXYLIC ACID, 5-ETHYL-5,8-DIHYDRO-8-OXO-, SODIUM SALT (1:1)
Common Name English
SODIUM 1-ETHYL-6,7-METHYLENEDIOXY-4-QUINOLONE-3-CARBOXYLATE
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
261-817-8
Created by admin on Sat Dec 16 07:50:45 UTC 2023 , Edited by admin on Sat Dec 16 07:50:45 UTC 2023
PRIMARY
PUBCHEM
23674254
Created by admin on Sat Dec 16 07:50:45 UTC 2023 , Edited by admin on Sat Dec 16 07:50:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID20208248
Created by admin on Sat Dec 16 07:50:45 UTC 2023 , Edited by admin on Sat Dec 16 07:50:45 UTC 2023
PRIMARY
SMS_ID
300000023728
Created by admin on Sat Dec 16 07:50:45 UTC 2023 , Edited by admin on Sat Dec 16 07:50:45 UTC 2023
PRIMARY
FDA UNII
8O78VP5TTM
Created by admin on Sat Dec 16 07:50:45 UTC 2023 , Edited by admin on Sat Dec 16 07:50:45 UTC 2023
PRIMARY
CAS
59587-08-5
Created by admin on Sat Dec 16 07:50:45 UTC 2023 , Edited by admin on Sat Dec 16 07:50:45 UTC 2023
PRIMARY
Related Record Type Details
Structure of OXOLINIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of OXOLINIC ACID
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