cinoxacin

Also known as Cinobac, 64716, 1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid, 5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylic acid, Cinoxacine, Cinoxacino, Cinoxacinum

Cinoxacin is a quinolone antibiotic that has been discontinued in the U.K. as well the United States, both as a branded drug or a generic. The marketing authorization of cinoxacin has been suspended throughout the EU.

In the Vinony graph

Within Vinony's link graph, cinoxacin is referenced by 117 other articles, and connects out to sulfamethazine, fidaxomicin and International Standard Book Number.

Vinony files it under Antimicrobials, Benzodioxoles and Cinnolines.

Its subject is documented across 12 Wikipedia language editions.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 460039276
Drug.IUPAC_name: 1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
Drug.image: Cinoxacin.svg
Drug.image_class: skin-invert-image
Drug.width: 260
Drug.MedlinePlus: a601013
Drug.legal_UK_comment: discontinued
Drug.legal_US_comment: discontinued
Drug.protein_bound: 60 to 80%
Drug.CAS_number: 28657-80-9
Drug.ATC_prefix: J01
Drug.ATC_suffix: MB06
Drug.PubChem: 2762
Drug.DrugBank: DB00827
Drug.ChemSpiderID: 2660
Drug.UNII: LMK22VUH23
Drug.KEGG: D00872

via Wikipedia infobox

Chemical data

Formula: C12H10N2O5
Molecular weight: 262.22 g/mol
IUPAC name: 1-ethyl-4-oxo-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
SMILES: CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
InChIKey: VDUWPHTZYNWKRN-UHFFFAOYSA-N
XLogP: 2.1
Polar surface area: 88.4 Å²
H-bond donors: 1
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1980
Admin. routes: oral
Indications: osteomyelitis, bacterial disease

via ChEMBL · EBI

Research

241 papers

Cinoxacin (Cinobac, Eli Lilly & Co.).Drug intelligence & clinical pharmacy · 1982
Cinoxacin: mechanism of action, spectrum of activity, pharmacokinetics, adverse reactions, and therapeutic indications.Pharmacotherapy · 1982
Cinoxacin. A review of its pharmacological properties and therapeutic efficacy in the treatment of urinary tract infections.Drugs · 1983
Cinoxacin: an overview.Urology · 1981
Influence of urinary pH on the pharmacokinetics of cinoxacin in humans and on antibacterial activity in vitro.Antimicrobial agents and chemotherapy · 1982

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 262.058971
Has use: medication

Show 6 more facts

chemical formula: C₁₂H₁₀N₂O₅
Commons category: Cinoxacin
medical condition treated: urinary tract infection
World Health Organisation international non-proprietary name: cinoxacin
canonical SMILES: CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
defined daily dose: 1

Sources (3)

via Wikidata · CC0

~6 min read

Encyclopedic overview

13 sections

Contents

History
Licensed uses
Availability
Mode of action
Contraindications
Adverse reactions
Overdose
Pharmacokinetics
Dosing
Impaired renal function
Susceptible bacteria
References
External links

Cinoxacin was an older synthetic antimicrobial related to the quinolone class of antibiotics with activity similar to oxolinic acid and nalidixic acid. It was commonly used thirty years ago to treat urinary tract infections in adults. There are reports that cinoxacin had also been used to treat initial and recurrent urinary tract infections and bacterial prostatitis in dogs. however this veterinary use was never approved by the United States Food and Drug Administration (FDA). In complicated UTI, the older gyrase-inhibitors such as cinoxacin are no longer indicated.

Excerpted from Wikipedia’s “cinoxacin” article, available under the CC BY-SA 4.0 licence.