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

• ChemBase编号: 706
• 分子式: C12H10N2O5
• 平均质量: 262.2182
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
• IUPAC传统名: cinoxacin
• 商标名: Cinobac
• 别名: Cinoxacin; Cinoxacin

登记号

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

理论计算性质

JChem

• Acid pKa: 4.930532
• 质子受体: 7
• 质子供体: 1
• LogD (pH = 5.5): 1.0434979
• LogD (pH = 7.4): -0.71855384
• Log P: 1.7161168
• 摩尔折射率: 73.6022 cm^3
• 极化性: 23.858301 Å^3
• 极化表面积: 88.43 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.25
• LOG S: -2.44
• 溶解度: 9.61e-01 g/l

分子性质

理化性质

• 疏水性(logP): 1.5

安全信息

• RTECS编号: JI4640000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: Others

产品相关信息

• 成盐信息: Free Base

详细说明

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.