Cinoxacin

Base Information

• Chemical Name: Cinoxacin
• CAS No.: 28657-80-9
• Molecular Formula: C12H10 N2 O5
• Molecular Weight: 262.222
• Hs Code.: 2934999090
• European Community (EC) Number: 249-133-8
• NSC Number: 756695,304467
• UNII: LMK22VUH23
• DSSTox Substance ID: DTXSID8022822
• Nikkaji Number: J3.169K
• Wikipedia: Cinoxacin
• Wikidata: Q1639588
• NCI Thesaurus Code: C65333
• Metabolomics Workbench ID: 43115
• ChEMBL ID: CHEMBL1208
• Mol file: 28657-80-9.mol

Synonyms:Acid, Azolinic;Azolinic Acid;Cinobac;Cinoxacin;Clinoxacin;Compound 64716

Chemical Property of Cinoxacin

Chemical Property:

• Vapor Pressure: 1.61E-11mmHg at 25°C
• Melting Point: 261-262° (dec)
• Refractive Index: 1.6660 (estimate)
• Boiling Point: 517.2°Cat760mmHg
• PKA: pKa 5.38(H2O t=25.0 I=0.025) (Uncertain)
• Flash Point: 266.6°C
• PSA: 90.65000
• Density: 1.64g/cm³
• LogP: 0.84330
• Storage Temp.: 2-8°C
• Solubility.: 1 M NaOH: soluble50mg/mL
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 262.05897142
• Heavy Atom Count: 19
• Complexity: 449

Purity/Quality:

99% ^*data from raw suppliers

Cinoxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
• Uses: antibacterial Cinoxacin is an antibacterial quinolone previously known for its use in the treatment of urinary tract infections.
• Therapeutic Function: Antibacterial
• Clinical Use: 1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5g]cinnoline-3-carboxylic acid (Cinobac) is a close congener (isostere) ofoxolinic acid (no longer marketed in the United States) andhas antibacterial properties similar to those of nalidixic andoxolinic acids. It is recommended for the treatment of urinary tract infectionscaused by strains of Gram-negative bacteria susceptibleto these agents. Early clinical studies indicate that thedrug possesses pharmacokinetic properties superior to thoseof either of its predecessors. Thus, following oral administration,higher urinary concentrations of cinoxacin thanof nalidixic acid or oxolinic acid are achieved. Cinoxacinappears to be more completely absorbed and less proteinbound than nalidixic acid.

Technology Process of Cinoxacin

There total 2 articles about Cinoxacin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

→ cinoxacin (28657-80-9)

Guidance literature:

Reference yield:

ethyl bromide (74-96-4) + 6,7-methylenedioxy-4(1H)-oxo-cinnolin-3-carboxylic acid ethylester (90447-46-4) + Aliquat 336 (5137-55-3,76925-99-0) → cinoxacin (28657-80-9)

Guidance literature:

With sodium hydroxide; potassium carbonate; In water; toluene;

Reference yield: 55.0%

cinoxacin (28657-80-9) + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + water (7732-18-5) + toluene (108-88-3,15644-74-3,16713-13-6) → chlorido(η6-p-cymene)(cinoxacinato-κ2O,O')ruthenium(II)*water*0.5toluene

Guidance literature:

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.;

DOI:10.1021/om101180c

upstream raw materials:

ethyl bromide

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

Aliquat 336

Downstream raw materials:

1-ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carbonitrile

1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)cinnolin-4(1H)-one

1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydrocinnolin-3-carboxamide

1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(piperidin-1-ylmethyl)cinnolin-4(1H)-one

Refernces