U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=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
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 Its use in human medicine has largely been replaced by the fluoroquinolone antibiotics.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
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
Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids.
1978 May
Assessment of temafloxacin neurotoxicity in rodents.
1991 Dec 30
[Drug-induced urolithiasis caused by N4-acetylsulfamethoxazole (Biseptol) and oxolinic acid (Desurol)].
1992 Nov
Anti-Mycobacterium avium activity of quinolones: in vitro activities.
1993 Sep
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 06:18:41 GMT 2023
Edited
by admin
on Sat Dec 16 06:18:41 GMT 2023
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
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 Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
NCI_THESAURUS C795
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
WHO-VATC QJ01MB05
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
Code System Code Type Description
ALANWOOD
oxolinic acid
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
DAILYMED
L0A22B22FT
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
CHEBI
138856
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
HSDB
3243
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
PUBCHEM
4628
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
WIKIPEDIA
OXOLINIC ACID
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
EVMPD
SUB09548MIG
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL416755
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
DRUG BANK
DB13627
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID1021089
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
NSC
110364
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
NCI_THESAURUS
C76921
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
INN
1866
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
DRUG CENTRAL
2024
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
RXCUI
7798
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m8314
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY Merck Index
MESH
D010093
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
FDA UNII
L0A22B22FT
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
CAS
14698-29-4
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
SMS_ID
100000083072
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
238-750-8
Created by admin on Sat Dec 16 06:18:41 GMT 2023 , Edited by admin on Sat Dec 16 06:18:41 GMT 2023
PRIMARY
Related Record Type Details
Structure of SODIUM OXOLINATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of OXOLINIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966