OXOLINIC ACID

US Previously Marketed

First approved in 1975

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 Search

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12

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

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 Its use in human medicine has largely been replaced by the fluoroquinolone antibiotics.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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015338.pdf	Curative		Approved 8429	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) 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

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) 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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A 22

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A 22	substrate 3367 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
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

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

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

OXOLINIC ACID

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

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