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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Inhibitor 8,297
Topoisomerase IV 62	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205	Curative		Not Provided 504	CINOBAC

C_max

Value	Dose	Analyte	Population
15.27 μg/mL	500 mg 1 times / day steady-state, oral	CINOXACIN serum	Homo sapiens
15.1 μg/mL	500 mg single, oral	CINOXACIN serum	Homo sapiens
14 μg/mL	500 mg single, oral	CINOXACIN serum	Homo sapiens
12.7 μg/mL	500 mg 2 times / day steady-state, oral	CINOXACIN serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
80.62 μg × h/mL	500 mg 1 times / day steady-state, oral	CINOXACIN serum	Homo sapiens
45.19 μg × h/mL	500 mg single, oral	CINOXACIN serum	Homo sapiens
78.4 μg × h/mL	500 mg single, oral	CINOXACIN serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
2.23 h	500 mg 1 times / day steady-state, oral	CINOXACIN serum	Homo sapiens
2.08 h	500 mg single, oral	CINOXACIN serum	Homo sapiens
2.27 h	500 mg single, oral	CINOXACIN serum	Homo sapiens
1.1 h	500 mg 2 times / day steady-state, oral	CINOXACIN serum	Homo sapiens

Sourcing

Sourcing

Show entries

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

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PubMed

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Title	Date	PubMed
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000 Oct	10991859
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry.	2002 Apr 5	12064523
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.	2005 May	16004377
Structure and medium effects on the photochemical behavior of nonfluorinated quinolone antibiotics.	2007 May-Jun	17132068

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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
Record UNII	LMK22VUH23
Record Status	`Validated (UNII)`
Record Version

Show entries

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

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Classification Tree

Code System

Code

Antibiotic

NCI_THESAURUS

C795

Other quinolones

WHO-ATC

J01MB06

Other quinolones

WHO-VATC

QJ01MB06

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Code System

Code

Type

Description

PUBCHEM

2762

PRIMARY

EVMPD

SUB06309MIG

PRIMARY

DRUG BANK

DB00827

PRIMARY

DRUG CENTRAL

657

PRIMARY

ChEMBL

CHEMBL1208

PRIMARY

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Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

[60 to 80] % (average)

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Related Record

Type

Details


					LMK22VUH23

CINOXACIN

ACTIVE MOIETY

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Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC	[1 to 1.5] hours (average)

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2