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C8645

Sigma-Aldrich

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:
28657-80-9
Molecular Weight:
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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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