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:
InChI key
VDUWPHTZYNWKRN-UHFFFAOYSA-N
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)
SMILES string
CCN1N=C(C(O)=O)C(=O)c2cc3OCOc3cc12
form
powder or crystals
antibiotic activity spectrum
Gram-negative bacteria
mode of action
DNA synthesis | interferes, enzyme | inhibits
Quality Level
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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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
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
S Jariyawat et al.
The Journal of pharmacology and experimental therapeutics, 290(2), 672-677 (1999-07-20)
In the present study, we investigated the interactions between antibiotics, especially beta-lactam antibiotics, and rat renal organic anion transporter 1 (OAT1). [(14)C]p-Aminohippurate (PAH) uptake via OAT1 expressed in Xenopus laevis oocytes was inhibited by all of the penicillins and cephalosporins
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 =
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