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Key Documents

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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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Ciprofloxacin ≥98% (HPLC)

Sigma-Aldrich

17850

Ciprofloxacin

Danofloxacin VETRANAL®, analytical standard

Supelco

33700

Danofloxacin

Levofloxacin 98.0-102.0% anhydrous basis (HPLC)

Sigma-Aldrich

28266

Levofloxacin

Sulfanilamide ≥98%

Sigma-Aldrich

S9251

Sulfanilamide

M Ruíz et al.
Journal of inorganic biochemistry, 69(4), 231-239 (1998-07-09)
Several cinoxacin (HCx) complexes with divalent metal ions have been prepared and characterized by spectroscopic techniques. The crystal structure of [Cd2(Cx)4(H2O)2].10H2O has been determined by X-ray diffraction. The complex is triclinic, space group P1 with unit-cell dimensions: a = 10.412(2)
Kazuaki Arai et al.
The Journal of antimicrobial chemotherapy, 66(3), 494-498 (2010-12-22)
Streptococcus pyogenes causes various diseases in humans. While the prevalence of fluoroquinolone-resistant S. pyogenes isolates has been increasing since 2000 in the USA and Europe, it has remained very low in Japan. We isolated a fluoroquinolone-resistant S. pyogenes strain and
D R Guay
Drug intelligence & clinical pharmacy, 16(12), 916-921 (1982-12-01)
Cinoxacin, a synthetic organic acid antibacterial agent, related structurally to nalidixic and oxolinic acid, has been approved for the treatment of initial and recurrent urinary tract infections (UTIs) caused by susceptible gram-negative microorganisms. The role of cinoxacin in the treatment
Franklin Vargas et al.
Journal of photochemistry and photobiology. B, Biology, 92(2), 83-90 (2008-06-20)
We have synthesized two naphthyl ester quinolone derivates and determined their ability to generate reactive oxygen species (ROS) such as (1)O(2), ()OH, H(2)O(2) upon photolysis with UV-A light. The ability of cinoxacin (1) and nalidixic acid (2), and their naphthyl
Lucija Peterlin-Masic et al.
Bioorganic & medicinal chemistry letters, 13(5), 789-794 (2003-03-06)
The design, synthesis and biological activity of non-covalent thrombin inhibitors incorporating 4,5,6,7-tetrahydroindazole, 2-methyl-4,5,6,7-tetrahydroindazole, 4,5,6,7-tetrahydroisoindole, 5,6,7,8-tetrahydroquinazoline and 5,6,7,8-tetrahydroquinazolin-2-amine as novel, partially saturated, heterobicyclic P(1)-arginine side-chain mimetics is described. The binding mode of the most potent candidate in the series co-crystallized with
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