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O0877

Sigma-Aldrich

Oxolinic acid

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
Beilstein:
620635
EC Number:
238-750-8
MDL number:
MFCD00056775
UNSPSC Code:
51282935
PubChem Substance ID:
24278604
NACRES:
NA.85

Quality Level

200

solubility

0.5 M NaOH: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

2-8°C

SMILES string

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

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)

InChI key

KYGZCKSPAKDVKC-UHFFFAOYSA-N

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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.

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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
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
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
Takashi Aoki et al.
Marine biotechnology (New York, N.Y.), 13(4), 629-638 (2010-04-16)
Shrimp aquaculture is one of the major foodproducing industries in the world. However, it is being impacted by several problems including diseases, antibiotic use, and environmental factors. The extent of the effects of these problems in the immune system of
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