C8645
Cinoxacin
Synonym(s):
1-Ethyl-1,4-dihydro-4-oxo-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C12H10N2O5
CAS Number:
Molecular Weight:
262.22
NACRES:
NA.85
PubChem Substance ID:
UNSPSC Code:
51102829
EC Number:
249-133-8
MDL number:
form
powder or crystals
Quality Level
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
Related Categories
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
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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
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
G Mendoza-Díaz et al.
Journal of inorganic biochemistry, 64(3), 207-214 (1996-11-15)
Studies of complexation equilibria of the antibiotic anions nalidixate and cinoxacinate with [Cu(phen)]2+ and [Cu(bipy)]2+ are reported. These studies indicate that the stability of this type of complex is strongly related to the metal environment. A correlation between the stability
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| C8645-5G | 04061833610329 |
| C8645-1G | 04061826754078 |
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