1-ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid

• ChemBase ID: 706
• Molecular Formular: C12H10N2O5
• Molecular Mass: 262.2182
• Monoisotopic Mass: 262.05897143
• SMILES: O1c2cc3n(nc(c(=O)c3cc2OC1)C(=O)O)CC
• Canonical SMILES: CCn1nc(C(=O)O)c(=O)c2c1cc1OCOc1c2
• InChI: 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)
• InChIKey: VDUWPHTZYNWKRN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
• IUPAC Traditional name: cinoxacin
• Brand Name: Cinobac
• Synonyms: Cinoxacin; Cinoxacin

Database IDs

• CAS Number: 28657-80-9
• EC Number: 249-133-8
• MDL Number: MFCD00056776
• PubChem SID: 24278343; 160964169; 46507547
• PubChem CID: 2762

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.930532
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.0434979
• LogD (pH = 7.4): -0.71855384
• Log P: 1.7161168
• Molar Refractivity: 73.6022 cm^3
• Polarizability: 23.858301 Å^3
• Polar Surface Area: 88.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.25
• LOG S: -2.44
• Solubility (Water): 9.61e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.5

Safety Information

• RTECS: JI4640000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00827

• Drug Groups: approved
• Description: Synthetic antimicrobial related to oxolinic acid and nalidixic acid and used in urinary tract infections. [PubChem]
• Indication: For the treatment of initial and recurrent urinary tract infections in adults caused by the following susceptible microorganisms: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella species (including K. pneumoniae), and Enterobacter species.
• Pharmacology: Cinoxacin is a synthetic antibacterial agent with in vitro activity against many gram-negative aerobic bacteria, particularly strains of the Enterobacteriaceae family. Cinoxacin inhibits bacterial deoxyribonucleic acid (DNA) synthesis, is bactericidal, and is active over the entire urinary pH range. Cross resistance with nalidixic acid has been demonstrated.
• Toxicity: Oral, subcutaneous, and intravenous LD₅₀ in the rat is 3610 mg/kg, 1380 mg/kg, and 860 mg/kg, respectively. Oral, subcutaneous, and intravenous LD₅₀ in the mouse is 2330 mg/kg, 900 mg/kg, and 850 mg/kg, respectively.Symptoms following an overdose of cinoxacin may include anorexia, nausea, vomiting, epigastric distress, and diarrhea. The severity of the epigastric distress and the diarrhea are dose related. Headache, dizziness, insomnia, photophobia, tinnitus, and a tingling sensation have been reported in some patients.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic, with approximately 30-40% metabolized to inactive metabolites.
• Absorption: Rapidly absorbed after oral administration. The presence of food delays absorption but does does not affect total absorption.
• Half Life: The mean serum half-life is 1.5 hours. Half-life in patients with impaired renal function may exceed 10 hours.
• Protein Binding: 60 to 80%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - C8645

Application
Cinoxacin is a synthetic antimicrobial commonly used in urinary tract infections that are caused by Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella species, and Enterobacter species.. It is a quinolone gyrase inhibitor. It is used to study the rat renal organic anion transporter 1 (OAT1)1. It is used to study fluoroquinolone-resistant Streptococcus pyogenes2.
Biochem/physiol Actions
Cinoxacin interferes with DNA replication by inhibiting DNA gyrase and topoisomerase IV (topo IV) through tight DNA binding. Cinoxacin allows for proper replicated DNA separation. Therefore, the inhibition of Cinoxacin inhibits DNA replication and cell division.
Cinoxacin interferes with DNA replication by inhibiting DNA gyrase and topoisomerase IV (topo IV) through tight DNA binding.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8645.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.