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
EC Number:
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
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 Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
A De Sarro et al.
General pharmacology, 24(6), 1393-1401 (1993-11-01)
1. The effects of some anticonvulsant drugs against seizures induced by a combined treatment with aminophylline and quinolone in genetically epilepsy-prone rat have been investigated. 2. Animals were intraperitoneally pretreated with carbamazepine, diazepam, phenobarbital, CPPene and dizocilpine or saline and
H S Brand et al.
Clinical and experimental rheumatology, 8(4), 393-395 (1990-07-01)
Explants of immature bovine articular cartilage were exposed to nalidixic acid, pipemidic acid and cinoxacin at one and ten times the human therapeutic plasma level for 7 days. Only nalidixic acid had significant effects on the chondrocyte metabolism. 20 micrograms/ml
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 P López-Gresa et al.
Journal of inorganic biochemistry, 92(1), 65-74 (2002-09-17)
Several novel metal-quinolone compounds have been synthesized and characterized by analytical, spectroscopic and X-ray diffraction methods. The crystal structure of the four compounds, Na(2)[(Cd(Cx)3)(Cd(Cx)3(H2O))].12H2O, [Co(Cp)2(H2O)2].9H2O, [Zn(Cp)2(H2O)2].8H2O and [Cd(HCp)2(Cl)2].4H2O, is presented and discussed: HCx=1-ethyl-1,4-dihydro-4-oxo(1,3)-dioxolo(4,5-g)cinnoline-3-carboxylic acid and HCp=1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid. In all
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