O0877

Oxolinic acid

Name: Oxolinic acid
Brand: SIGMA

quinolone antibiotic

Synonym(s):

5,8-Dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₁NO₅

CAS Number:

14698-29-4

Molecular Weight:

261.23

UNSPSC Code:

51282935

NACRES:

NA.85

PubChem Substance ID:

24278604

EC Number:

238-750-8

Beilstein/REAXYS Number:

620635

MDL number:

MFCD00056775

Key Documents

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InChI key

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)

SMILES string

CCN1C=C(C(O)=O)C(=O)c2cc3OCOc3cc12

Quality Level

200

antibiotic activity spectrum

Gram-negative bacteria

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

2-8°C

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Antibiotics

Biochemicals

Cell Culture Supplements & Reagents

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Show Differences

1 of 4

This Item	67126	O0240000	C8645
Sigma-Aldrich O0877 Oxolinic acid	Supelco 67126 Oxolinic acid	O0240000 Oxolinic acid	Sigma-Aldrich C8645 Cinoxacin
antibiotic activity spectrum Gram-negative bacteria	antibiotic activity spectrum -	antibiotic activity spectrum -	antibiotic activity spectrum Gram-negative bacteria
mode of action DNA synthesis \| interferes, enzyme \| inhibits	mode of action -	mode of action -	mode of action DNA synthesis \| interferes, enzyme \| inhibits
Quality Level 200	Quality Level 100	Quality Level -	Quality Level 200
solubility 0.5 M NaOH: soluble 50 mg/mL	solubility -	solubility -	solubility -
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. -

General description

Chemical structure: quinolone

Application

Oxolinic acid is used to study new transmissible resistance mechanisms qnrA, qnrB, qnrS, and aac(6′)Ib-cr, in Escherichia coli and Salmonella enterica. Oxolinic acid is added to culture medium for the isolation of Gardnerella vaginalis[1].

Biochem/physiol Actions

Oxolinic acid is a quinolone antibiotic. It is a DNA-gyrase (topoisomerase II) inhibitor used for studies on DNA winding and coiling and acts as a dopamine reuptake inhibitor for studies on dopaminergic neurotransmission processes.

Other Notes

5g,25g

Keep container tightly closed in a dry and well-ventilated place.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Behavioural and neurochemical evidence that the antimicrobial agent oxolinic acid is a dopamine uptake inhibitor.

J Garcia de Mateos-Verchere et al.

European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, 8(4), 255-259 (1999-02-03)

The antimicrobial agent oxolinic acid, injected i.p. in mice, induced a dose dependent increase in locomotor activity. This stimulation culminated at the 32 mg/kg dose and became smaller for higher doses (64-128 mg/kg). When opposed to increasing doses (50-100-200 microg/kg

Colistin-oxolinic acid blood agar: a selective medium for the isolation of Gardnerella vaginalis.

J S Thompson

Journal of clinical microbiology, 21(5), 843-843 (1985-05-01)

Colistin-oxolinic acid medium is proposed as a selective isolation medium for Gardnerella vaginalis. The medium is effective in inhibiting staphylococci and gram-negative bacteria while allowing growth of G. vaginalis.

Contribution of reactive oxygen species to pathways of quinolone-mediated bacterial cell death.

Xiuhong Wang et al.

The Journal of antimicrobial chemotherapy, 65(3), 520-524 (2010-01-14)

Quinolone-mediated death of Escherichia coli has been proposed to occur by two pathways. One is blocked by inhibitors of protein synthesis; the other is not. It is currently unknown how these two pathways fit with the recent observation that hydroxyl

Suppression of pine wilt disease by an antibacterial agent, oxolinic acid.

Hyeok Ran Kwon et al.

Pest management science, 66(6), 634-639 (2010-02-13)

Pine wilt disease (PWD) is very complex and has been reported to be caused by pine wood nematode, Bursaphelenchus xylophilus (Steiner & Buhrer) Nickle, and its accompanying bacteria. However, there is no report on the control of PWD by antibacterial

Zinc complexes of the antibacterial drug oxolinic acid: structure and DNA-binding properties.

Alketa Tarushi et al.

Journal of inorganic biochemistry, 103(6), 898-905 (2009-04-28)

The neutral mononuclear zinc complexes with the quinolone antibacterial drug oxolinic acid in the absence or presence of a nitrogen donor heterocyclic ligand 2,2'-bipyridine or 1,10-phenanthroline have been synthesized and characterized. The experimental data suggest that oxolinic acid is on

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