SODIUM OXOLINATE

US Previously Marketed

First approved in 1975

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 Search

SMILES

[Na+].CCN1C=C(C([O-])=O)C(=O)C2=C1C=C3OCOC3=C2

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

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68010093 | https://www.ncbi.nlm.nih.gov/pubmed/9928913 | http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015338.pdf

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 Its use in human medicine has largely been replaced by the fluoroquinolone antibiotics.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 Target	Pharmacology	Condition	Potency
DNA topoisomerase medium subunit 2 Target ID: P07065 Gene ID: 1258768.0 Gene Symbol: 52.0 Target Organism: Enterobacteria phage T4 (Bacteriophage T4) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12069589	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015338.pdf	Curative		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A 26

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A 26	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/10.1111/are.12197 Page: 6.0	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004-04	15047530
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000-10	10991859
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.	2000-10	10991858
Anti-Mycobacterium avium activity of quinolones: in vitro activities.	1993-09	8239587
[Drug-induced urolithiasis caused by N4-acetylsulfamethoxazole (Biseptol) and oxolinic acid (Desurol)].	1992-11	1480987
Assessment of temafloxacin neurotoxicity in rodents.	1991-12-30	1662895
The proconvulsive activity of quinolone antibiotics in an animal model.	1991-09	1897004
The calcium entry blockers: anti-manic drugs?	1986	3809523
Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids.	1978-05	660597

Patents

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.

Name

Type

Language

1,3-DIOXOLO(4,5-G)QUINOLINE-7-CARBOXYLIC ACID, 5-ETHYL-5,8-DIHYDRO-8-OXO-, SODIUM SALT

Preferred Name

English

SODIUM OXOLINATE

Systematic 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