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28657-80-9

Basic Information
CAS No.: 28657-80-9
Name: CINOXACIN
Article Data: 3
Molecular Structure:
Molecular Structure of 28657-80-9 (CINOXACIN)
Formula: C12H10 N2 O5
Molecular Weight: 262.222
Synonyms: 1-Ethyl-3-carboxy-6,7-methylenedioxy-4-cinnolone;Cinobac; Cinobactin; Cinoxacin; Compound 64716; NSC 304467; Noxigram; Uronorm
Density: 1.64g/cm3
Melting Point: 261-262° (dec)
Boiling Point: 517.2°Cat760mmHg
Flash Point: 266.6°C
Safety: Moderately toxic by ingestion, subcutaneous and intravenous routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
PSA: 90.65000
LogP: 0.84330
Synthetic route
74-96-4

ethyl bromide

90447-46-4

6,7-methylenedioxy-4(1H)-oxo-cinnolin-3-carboxylic acid ethylester

5137-55-3

Aliquat 336

28657-80-9

cinoxacin

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate In water; toluene
28657-80-9

cinoxacin

sodium hexaflorophosphate

64-17-5

ethanol

[Ru([9]aneS3)(dmso)3](PF6)2

[Ru([9]aneS3)(dmso-κS)(cin-κ2O,O)](PF6)*EtOH

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Reflux;92.9%
28657-80-9

cinoxacin

nickel(II) sulfate heptahydrate

67-68-5

dimethyl sulfoxide

{Ni(1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylate)2(dimethyl sulfoxide)2}*4H2O

B

151933-03-8

{Ni(1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylate)2(H2O)2}

Conditions
ConditionsYield
With NaOH; H2O In dimethyl sulfoxide mixing DMSO soln. of cinoxacin and of the Ni salt, slow addn. of 5 ml of aq. NaOH with stirring, crystn. of Ni(cinoxacinate)2*2H2O after 1 d; filtration, washing (water), drying at 90°C, crystn. of the Ni complex contg. dimethyl sulfoxide ligands after 2-3 months from the remaining soln., filtration, drying at room temp., elem. anal.;A 10%
B 80%
28657-80-9

cinoxacin

95-14-7

1,2,3-Benzotriazole

1173208-74-6

3-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-1-ethyl-[1,3]dioxolo[4,5-g]cinnolin-4(1H)-one

Conditions
ConditionsYield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 25℃; for 0.5h;
Stage #2: cinoxacin In dichloromethane at 25℃; for 2h;
80%
28657-80-9

cinoxacin

67-68-5

dimethyl sulfoxide

7646-85-7

zinc(II) chloride

A

{Zn(1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylate)2}*4H2O

{Zn(1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylate)2(dimethyl sulfoxide)2}*4H2O

Conditions
ConditionsYield
With NaOH; H2O In dimethyl sulfoxide mixing of a DMSO soln. of cinoxacin and of ZnCl2, addn. of 1 ml of aq. NaOH with stirring, pptn. of Zn(cinoxacinate)2*4H2O after 12-14 d; filtration, washing (water), drying at 90°C, remaining soln. standing at room temp., crystn. of the Zn complex (contg. additionally DMSO ligands) after a few d, filtration, drying at room temp., elem. anal.;A 75%
B 6%
28657-80-9

cinoxacin

1429439-48-4

1-ethyl-5-nitro-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnolin-3-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid; potassium nitrate at 0 - 20℃; for 13h; Inert atmosphere;75%
28657-80-9

cinoxacin

67-56-1

methanol

1429438-89-0

methyl 1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnolin-3-carboxylate

Conditions
ConditionsYield
Stage #1: cinoxacin With boron tribromide In dichloromethane at -30 - 20℃; for 41h; Inert atmosphere;
Stage #2: methanol In dichloromethane at -30 - 20℃; Inert atmosphere;
74.5%
28657-80-9

cinoxacin

A

109773-20-8

1-Ethyl-1H-[1,3]dioxolo[4,5-g]cinnolin-4-one

B

1-Ethyl-3-hydroxy-1H-[1,3]dioxolo[4,5-g]cinnolin-4-one

Conditions
ConditionsYield
With oxygen In methanol for 12h; Ambient temperature; Irradiation; in PBS-solution (pH=8); Yields of byproduct given;A n/a
B 62%
With oxygen In methanol for 12h; Mechanism; Product distribution; Ambient temperature; Irradiation; Iin PBS-solution (pH=8);
With oxygen In methanol for 12h; Ambient temperature; Irradiation; in PBS-solution (pH=8); Yields of byproduct given;A 0.580 mol
B n/a
28657-80-9

cinoxacin

5'-monomethoxytrityl-protected 5'-amino-5'-deoxythymidine phosphoramidite

5'-monomethoxytrityl-protected 5'-amino-5'-deoxythymidine phosphoramidite

dGdCdGdCdA-resin

dGdCdGdCdA-resin

cinoxacin 5'-amino-5'-deoxydTdGdCdGdCdA

Conditions
ConditionsYield
Multistep reaction.;55%
28657-80-9

cinoxacin

52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

108-88-3

toluene

chlorido(η6-p-cymene)(cinoxacinato-κ2O,O')ruthenium(II)*water*0.5toluene

Conditions
ConditionsYield
With NaOCH3 In methanol; chloroform byproducts: NaCl; addn. of sodium methylate to soln. of ruthenium compd. and sodium nalidixicate in CHCl3/methanol (1/1), refluxing for 6 h; filtration through celite, addn. of toluene, keeping at room temp. with slow evapn. for 3 d, isolation of crystals, washing with hexane, elem. anal.;55%
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Chemistry

Product Name: Cinoxacin (CAS NO.28657-80-9)


Molecular Formula: C12H10N2O5
Molecular Weight: 262.22g/mol
Mol File: 28657-80-9.mol
Einecs: 249-133-8
Appearance: Light tan crystals
Boiling point: 517.2 °C at 760 mmHg
Density: 1.64 g/cm3
Surface Tension: 65.7 dyne/cm
Enthalpy of Vaporization: 83.11 kJ/mol
Vapour Pressure: 1.61E-11 mmHg at 25°C
XLogP3-AA: 2.1
H-Bond Donor: 1
H-Bond Acceptor: 7
Product Categories: Interferes with DNA SynthesisAntibiotics; Quinolones and FluoroquinolonesMore...Close...; A - KAntibiotics; Antibacterial; Antibiotics A to; Antibiotics A-FAntibiotics; Antibiotics by Application; Antineoplastic and Immunosuppressive AntibioticsAntibiotics; Chemical Structure Class; Inhibits an EnzymeAntibiotics; Mechanism of Action; Spectrum of Activity

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 850mg/kg (850mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 28(Suppl,
mouse LD50 oral 2330mg/kg (2330mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 28(Suppl,
mouse LD50 subcutaneous 900mg/kg (900mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 28(Suppl,
rat LD50 intravenous 860mg/kg (860mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 28(Suppl,
rat LD50 oral 3610mg/kg (3610mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 28(Suppl,
rat LD50 subcutaneous 1380mg/kg (1380mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 28(Suppl,

Safety Profile

Moderately toxic by ingestion, subcutaneous and intravenous routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Specification

 Cinoxacin ,its CAS NO. is 28657-80-9,the synonyms is 1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid;cinoxacin ; Timtec-bb sbb003082 ; 1-Ethyl-6,7-methylenedioxy-4(1h)-oxocinnoline-3-carboxylicacid ; 3)Dioxolo(4,5-g)cinnoline-3-carboxylicacid,1,4-dihydro-1-ethyl-4-oxo-( ; Cinobac ; 1-Ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid .