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Merck

O0877

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
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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Quality Level

200

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

signalword

Warning

hcodes

H302

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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Certificates of Analysis (COA)

Lot/Batch Number
078K1608
018K1272
127H1189
115K1782
112K1257

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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
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.
Kalliopi C Skyrianou et al.
Journal of inorganic biochemistry, 104(2), 161-170 (2009-11-27)
The mononuclear nickel(II) complexes with the first-generation quinolone antibacterial agent oxolinic acid in the presence or absence of nitrogen-donor heterocyclic ligands (2,2'-bipyridine, 1,10-phenanthroline or pyridine) have been synthesized and characterized. The experimental data suggest that oxolinic acid acts as deprotonated
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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