C8645

Sigma-Aldrich

Cinoxacin

Synonym(s):
1-Ethyl-1,4-dihydro-4-oxo-1,3dioxolo4,5-gcinnoline-3-carboxylic acid
Empirical Formula (Hill Notation):
C12H10N2O5
CAS Number:
Molecular Weight:
262.22
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85
Pricing and availability is not currently available.

form

powder or crystals

Mode of action

DNA synthesis | interferes
enzyme | inhibits

antibiotic activity spectrum

Gram-negative bacteria

SMILES string

CCN1N=C(C(O)=O)C(=O)c2cc3OCOc3cc12

InChI

1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)

InChI key

VDUWPHTZYNWKRN-UHFFFAOYSA-N

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General description

Chemical structure: quinolone

Application

Cinoxacin was used to study the rat renal organic anion transporter 1 (OAT1). It is used to study fluoroquinolone-resistant Streptococcus pyogenes.

Biochem/physiol Actions

Cinoxacin is a synthetic antimicrobial agent that interferes with DNA replication by inhibiting DNA gyrase and topoisomerase IV (topo IV) through tight DNA binding. The mechanism of action of cinoxacin is comparable to nalidixic acid. Cinoxacin is effective against Gram-negative bacteria and is often used to treat urinary tract infections caused by E. coli, Proteus mirabilis, Proteus vulgaris and Klebsiella sp.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8645.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
M Ruiz et al.
Journal of inorganic biochemistry, 59(4), 801-810 (1995-09-01)
The structural and spectroscopic properties of a new copper (II) complex of cinoxacin (HCx) have been investigated. The complex [Cu(Cx)2].2H2O crystallizes in the monoclinic system, space group P2(1)/c. The cell dimensions are: a = 7.998(2), b = 7.622(1), c =...
U Neugebauer et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 61(7), 1505-1517 (2005-04-12)
Quinolones are important gyrase inhibitors. Even though they are used as active agents in many antibiotics, the detailed mechanism of action on a molecular level is so far not known. It is of greatest interest to shed light on this...
J M Scavone et al.
Pharmacotherapy, 2(5), 266-272 (1982-09-01)
Cinoxacin, a chemotherapeutic agent that inhibits bacterial DNA synthesis, has recently been approved for the treatment of initial and recurrent bacterial urinary tract infections. Although closely related to nalidixic acid, cinoxacin possesses some distinct characteristics: rapid attainment of therapeutic urinary...
T S Sisca et al.
Drugs, 25(6), 544-569 (1983-06-01)
Cinoxacin is a urinary antibacterial drug closely related structurally to nalidixic acid. It has a spectrum of in vitro antibacterial activity which qualitatively resembles that of the latter agent, covering most common Gram-negative pathogens, excluding Pseudomonas. In acute or recurrent...
I Durán Merás et al.
The Analyst, 125(8), 1471-1476 (2000-09-26)
Nalidixic acid, 7-hydroxymethylnalidixic acid, oxolinic acid, pipemidic acid and cinoxacine form complexes with zinc(II) in the presence of acetate buffer of pH 5.5 and oxolinic acid, pipemidic acid and cinoxacine form complexes with aluminium(III) in the presence of chloroacetate buffer...

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