| Version |
2.5 |
| Creation Date |
2005-06-13 13:24:05 |
| Update Date |
2009-06-23 18:07:19 |
| Primary Accession Number |
DB00827 |
| Secondary Accession Number |
|
| Name |
Cinoxacin |
| Drug Type |
|
| Description |
Synthetic antimicrobial related to oxolinic acid and nalidixic acid and used in urinary tract infections. [PubChem] |
| Synonyms |
Not Available |
| Brand Names |
- Cinobac
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
1-ethyl-4-oxo-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid |
| Chemical Formula |
C12H10N2O5 |
| Chemical Structure |
 |
| CAS Registry Number |
28657-80-9 |
| InChI Identifier |
InChI=1/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)/f/h16H |
| InChI Key |
VDUWPHTZYNWKRN-WYUMXYHSCG |
| KEGG Drug |
D00872  |
| KEGG Compound |
C08052  |
| PubChem Compound |
2762  |
| PubChem Substance |
10252  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA449007  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available |
| RxList Link |
http://www.rxlist.com/cgi/generic3/cinobac.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Cinoxacin  |
| FDA Label |
|
| Material Safety Data Sheet (MSDS) |
|
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
262.2182 |
| Monoisotopic Molecular Weight |
262.0590 |
| State |
Solid |
| Melting Point |
261 oC |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
9.61e-01 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
1.5
Source: PhysProp
|
| Predicted LogP |
1.25
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-2.44
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
Not Available |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12 |
| Canonical SMILES |
CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12 |
| Drug Category |
|
| ATC Codes |
|
| AHFS Codes |
Not Available |
| 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. |
| Mechanism of Action |
Evidence exists that cinoxacin binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis. |
| Absorption |
Rapidly absorbed after oral administration. The presence of food delays absorption but does does not affect total absorption. |
| 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. |
| Protein Binding |
60 to 80% |
| Biotransformation |
Hepatic, with approximately 30-40% metabolized to inactive metabolites. |
| Half Life |
The mean serum half-life is 1.5 hours. Half-life in patients with impaired renal function may exceed 10 hours. |
| Dosage Forms |
|
| Patient Information |
Show  |
| Contraindications |
Show  |
| Interactions |
Show  |
| Drug Interactions |
Not Available
|
| Food Interactions |
Not Available
|
| Pathways |
Not Available
|
| General References |
- Wikipedia

- RxList

|
| Organisms Affected |
- Enteric bacteria and other eubacteria
|
| Targets |
- DNA
|
|
Drug Target 1
[top]
|
| Target 1 ID |
874 |
| Target 1 Name |
DNA |
| Target 1 Synonyms |
- Deoxyribonucleic acid
|
| Target 1 Gene Name |
Not Available |
| Target 1 Protein Sequence |
Not Available |
| Target 1 Number of Residues |
0 |
| Target 1 Molecular Weight |
7656 (double strand) |
| Target 1 Theoretical pI |
Not Available |
| Target 1 GO Classification |
|
Function
|
information storage
information transfer
|
|
Process
|
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
|
|
Component
|
cell
intracellular
nucleus
mitochondria |
|
| Target 1 General Function |
Biological information storage and information transfer |
| Target 1 Specific Function |
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes. |
| Target 1 Pathways |
|
| Target 1 Reactions |
- DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
|
| Target 1 Pfam Domain Function |
Not Available |
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
|
| Target 1 Essentiality |
Essential |
| Target 1 GenBank ID Protein |
Not Available |
| Target 1 UniProtKB/Swiss-Prot ID |
Not Available |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
Not Available |
| Target 1 PDB ID |
1BNA  |
| Target 1 PDB File |
Show |
| Target 1 3D Structure |
|
| Target 1 Cellular Location |
|
| Target 1 Gene Sequence |
>Example: Dickerson dodecamer
CGCGAATTCGCG
|
| Target 1 GenBank Gene ID |
|
| Target 1 GeneCard ID |
Not Available |
| Target 1 GenAtlas ID |
Not Available |
| Target 1 HGNC ID |
Not Available |
| Target 1 Chromosome Location |
Not Available |
| Target 1 Locus |
All loci |
| Target 1 SNPs |
Not Available |
| Target 1 General References |
- Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed
]
|
| Target 1 Drug References |
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed
]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed
]
|