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

Molecular Formula	C12H10N2O5
Molecular Weight	262.2182
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
Corneal and scleral permeability of quinolones--a pharmacokinetics study.	2003 Dec	14733712
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
Structure and medium effects on the photochemical behavior of nonfluorinated quinolone antibiotics.	2007 May-Jun	17132068
Antimicrobial resistance patterns of Shiga toxin-producing Escherichia coli O157:H7 and O157:H7- from different origins.	2007 Spring	17536933
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:22:45 GMT 2023` Edited by `admin` on `Fri Dec 15 15:22:45 GMT 2023`
Record UNII	LMK22VUH23
Record Status	`Validated (UNII)`
Record Version

Download

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