CINOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H10N2O5
Molecular Weight	262.2182
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1N=C(C(O)=O)C(=O)C2=C1C=C3OCOC3=C2

InChI

InChIKey=VDUWPHTZYNWKRN-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/18067s29lbl.pdf

Cinoxacin is a synthetic antibacterial agent for oral administration. Cinoxacin mode of action involves the inhibiting of DNA gyrase, a type II topoisomerase, and topoisomerase IV. Adverse effects are nausea, anorexia, vomiting, abdominal cramps/pain, perverse taste, diarrhea, headache, dizziness, rash, urticaria, pruritus, edema and other.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://ptfarm.pl/pub/File/Acta_Poloniae/1999/1/011.pdf	Inhibitor 8297
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: ISBN-13: 978-0896038424	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/18067s29lbl.pdf	Curative		Not Provided 504	CINOBAC Approved Use Cinobac is indicated 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. Launch Date 1980

C_max

Value	Dose	Analyte	Population
15.27 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3665628	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
15.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6653617	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CINOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3665628	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/507797	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
80.62 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3665628	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
45.19 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6653617	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CINOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
78.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3665628	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3665628	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6653617	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CINOXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.27 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3665628	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/507797	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CINOXACIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3716	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3716
ChemicalBook	CB3200706	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3200706
MolPort	MolPort-001-794-447	https://www.molport.com/shop/molecule-link/MolPort-001-794-447
ZINC	ZINC000000032350	http://zinc15.docking.org/substances/ZINC000000032350
eMolecules	536545	https://www.emolecules.com/cgi-bin/more?vid=536545

PubMed

Title	Date	PubMed
A clinical comparison of cinoxacin and nalidixic acid in the treatment of urinary tract infection.	1981 Jun	7017171
[A comparison of cinoxacin and nalidixic acid in the treatment of chronic urinary tract infections].	1982	7129643
Review of adverse reactions associated with cinoxacin and other drugs used to treat urinary tract infections.	1984 Jan	6362163
Repeated treatment with quinolones potentiates the seizures induced by aminophylline in genetically epilepsy-prone rats.	1992 Sep	1426928
Only some anticonvulsants protect against seizures induced by aminophylline in quinolone-treated genetically epilepsy prone rats.	1993 Nov	8112511
Effects of some quinolones on imipenem-induced seizures in DBA/2 mice.	1994 Mar	8026738
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000 Oct	10991859
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.	2000 Oct	10991858
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
On the effect of covalently appended quinolones on termini of DNA duplexes.	2002 Apr 24	11960452
Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry.	2002 Apr 5	12064523
Transformation of cinoxacin by Beauveria bassiana.	2002 Aug 27	12204384
Separation of levofloxacin, ciprofloxacin, gatifloxacin, moxifloxacin, trovafloxacin and cinoxacin by high-performance liquid chromatography: application to levofloxacin determination in human plasma.	2002 May 25	12016015
Validation of a liquid chromatography-tandem mass spectrometry method for the simultaneous quantification of 11 (fluoro)quinolone antibiotics in swine kidney.	2002 Nov 8	12462610
Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin). Spectroscopic and X-ray structural characterization. Antibacterial studies.	2002 Sep 30	12230989
Photo-induced interaction of antibacterial quinolones with human serum albumin.	2003	20021162
Corneal and scleral permeability of quinolones--a pharmacokinetics study.	2003 Dec	14733712
Anaphylactic reaction to cinoxacin: report of one case associated with inferior acute myocardial infarction.	2003 Feb	12674041
Novel thrombin inhibitors incorporating non-basic partially saturated heterobicyclic P1-arginine mimetics.	2003 Mar 10	12617892
Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin.	2004 Dec	15909943
Endosymbiotic alga from green hydra under the influence of cinoxacin.	2005	16295658
Selective action of fluoroquinolones against intracellular amastigotes of Leishmania (Viannia) panamensis in vitro.	2005 Dec	16539034
Acute ST-segment elevation myocardial infarction after amoxycillin-induced anaphylactic shock in a young adult with normal coronary arteries: a case report.	2005 Feb 25	15733315
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.	2005 May	16004377
Vibrational spectroscopic characterization of fluoroquinolones.	2005 May	15820884
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).	2006 Apr 19	16608195
Structure and medium effects on the photochemical behavior of nonfluorinated quinolone antibiotics.	2007 May-Jun	17132068
UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs.	2007 Nov 11	19662185
Phenotypic and genotypic antimicrobial resistance patterns of Escherichia coli isolated from dairy cows with mastitis.	2007 Oct 6	17544234
Antimicrobial resistance patterns of Shiga toxin-producing Escherichia coli O157:H7 and O157:H7- from different origins.	2007 Spring	17536933
Synthesis, primary photophysical and antibacterial properties of naphthyl ester cinoxacin and nalidixic acid derivatives.	2008 Aug 21	18562206
Trace analysis of quinolone and fluoroquinolone antibiotics from wastewaters by liquid chromatography-electrospray tandem mass spectrometry.	2008 Dec 19	19007934
Gradient HPLC of antibiotics in urine, ground water, chicken muscle, hospital wastewater, and pharmaceutical samples using C-18 and RP-amide columns.	2008 Feb	18183552
Allergic reactions to oral drugs: A case/non-case study from an Italian spontaneous reporting database (GIF).	2008 Sep-Oct	18692136
Synthesis, characterization, antibacterial and anti-inflammatory activities of enoxacin metal complexes.	2009	19657456
Synthesis, characterization, and biological activity studies of copper(II) mixed compound with histamine and nalidixic acid.	2009	19557138
Synthesis of amino acid derivatives of quinolone antibiotics.	2009 Jun 7	19462046
Protection Afforded by Fluoroquinolones in Animal Models of Respiratory Infections with Bacillus anthracis, Yersinia pestis, and Francisella tularensis.	2010 Jun 3	21127743
Quantitation of fluoroquinolones in honey using tandem mass spectrometry (LC-MS/MS): nested validation with two mass spectrometers.	2010 Sep-Oct	21140677
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage for the treatment of urinary tract infections is 1 g daily, administered orally in 2 or 4 divided doses (500 mg b.i.d. or 250 mg q.i.d. respectively) for 7 to 14 days.

Route of Administration: Oral

In Vitro Use Guide

MIC for Proteus mirabilis and E. coli = 0.5 to 32 ug/ml

Name

Type

Language

CINOXACIN

Official Name

English

1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid

Systematic Name

English

CINOXACIN [MART.]

Common Name

English

64716

Code

English

NSC-304467

Code

English

CINOXACIN [USAN]

Common Name

English

(1,3)DIOXOLO(4,5-G)CINNOLINE-3-CARBOXYLIC ACID, 1-ETHYL-1,4-DIHYDRO-4-OXO

Common Name

English

CINOXACIN [ORANGE BOOK]

Common Name

English

CINOBAC

Brand Name

English

CINOXACIN [JAN]

Common Name

English

cinoxacin [INN]

Common Name

English

CINOXACIN [MI]

Common Name

English

CINOXACIN [VANDF]

Common Name

English

CINOXACIN [USP IMPURITY]

Common Name

English

Cinoxacin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795