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C8645

Sigma-Aldrich

Cinoxacin

Sinónimos:

1-Ethyl-1,4-dihydro-4-oxo-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid

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About This Item

Fórmula empírica (notación de Hill):
C12H10N2O5
Número de CAS:
28657-80-9
Peso molecular:
262.22
EC Number:
249-133-8
MDL number:
MFCD00056776
UNSPSC Code:
51102829
PubChem Substance ID:
24278343
NACRES:
NA.85

form

powder or crystals

antibiotic activity spectrum

Gram-negative bacteria

mode of action

DNA synthesis | interferes
enzyme | inhibits

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

17850

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Danofloxacin VETRANAL®, analytical standard

Supelco

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Levofloxacin 98.0-102.0% anhydrous basis (HPLC)

Sigma-Aldrich

28266

Levofloxacin

Sulfanilamide ≥98%

Sigma-Aldrich

S9251

Sulfanilamide

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
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
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 =
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
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
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