Nadifloxacin

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H21FN2O4
Molecular Weight	360.3794
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1CCC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N4CCC(O)CC4

InChI

InChIKey=JYJTVFIEFKZWCJ-UHFFFAOYSA-N

InChI=1S/C19H21FN2O4/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21/h8-11,23H,2-7H2,1H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula	C19H21FN2O4
Molecular Weight	360.3794
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/15795123
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/15452398

Nadifloxacin (INN, brand names Acuatim, Nadiflox, Nadoxin, Nadixa, activon) is a topical fluoroquinolone antibiotic for the treatment of acne vulgaris. It is also used to treat bacterial skin infections. In vitro studies of nadifloxacin showed potent and broad-spectrum antibacterial activity against aerobic Gram-positive, Gram-negative and anaerobic bacteria, including Propionibacterium acnes and Staphylococcus epidermidis. Nadifloxacin inhibits the enzyme DNA gyrase that is involved in bacterial DNA synthesis and replication, thus inhibiting the bacterial multiplication. In some European countries, the drug has been approved for the treatment of acne vulgaris. In a 2013 multicenter, randomized clinical study with a total of 184 Japanese patients with moderate to severe acne, adapalene 0.1% gel plus nadifloxacin 1% cream (combination therapy) showed a significant efficacy in decrement of inflammatory papulopustular lesions. Despite this it should be noted that in patients with skin lesions, topical application of nadifloxacin can result in plasma concentrations of 1 to 3 ng/ml. During the treatment some patients may develop some adverse effects predominantly of the skin and subcutaneous tissue: burning and itching (in absolute the most common side effect), contact dermatitis, dryness and skin irritation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase 26 Target ID: CHEMBL3038482 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11810583	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acne vulgaris 34 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21342170	Curative		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
4 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/17020421/	600 mg single, intravenous dose: 600 mg route of administration: Intravenous experiment type: SINGLE co-administered:		LEVONADIFLOXACIN unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 h REVIEW https://pubmed.ncbi.nlm.nih.gov/17020421/	600 mg single, intravenous dose: 600 mg route of administration: Intravenous experiment type: SINGLE co-administered:		LEVONADIFLOXACIN unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.tandfonline.com/doi/abs/10.3109/09546639709160277 https://pubmed.ncbi.nlm.nih.gov/17020421/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.tandfonline.com/doi/abs/10.3109/09546639709160277 https://pubmed.ncbi.nlm.nih.gov/17020421/	Disc. AE: Itching, Erythema... AEs leading to discontinuation/dose reduction: Itching (grade 3, 0.01%) Erythema (grade 3, 0.01%) Sources: https://www.tandfonline.com/doi/abs/10.3109/09546639709160277 https://pubmed.ncbi.nlm.nih.gov/17020421/

AEs

AE	Significance	Dose	Population
Erythema	grade 3, 0.01% Disc. AE	1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.tandfonline.com/doi/abs/10.3109/09546639709160277 https://pubmed.ncbi.nlm.nih.gov/17020421/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.tandfonline.com/doi/abs/10.3109/09546639709160277 https://pubmed.ncbi.nlm.nih.gov/17020421/
Itching	grade 3, 0.01% Disc. AE	1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.tandfonline.com/doi/abs/10.3109/09546639709160277 https://pubmed.ncbi.nlm.nih.gov/17020421/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.tandfonline.com/doi/abs/10.3109/09546639709160277 https://pubmed.ncbi.nlm.nih.gov/17020421/

PubMed

Title	Date	PubMed
Topical nadifloxacin 1% cream vs. topical erythromycin 4% gel in the treatment of mild to moderate acne.	2010-12	21091683
Besifloxacin: a novel anti-infective for the treatment of bacterial conjunctivitis.	2010-04-26	20463787
Pseudomonas fingernail infection successfully treated with topical nadifloxacin in HIV-positive patients: report of two cases.	2010-04-24	20386383
Cetuximab-induced skin exanthema: Improvement by a reactive skin therapy.	2010-04-09	21472315
A modified surgical technique for steatocystoma multiplex.	2010-01	20606990
Topical therapy with nadifloxacin cream and prednicarbate cream improves acneiform eruptions caused by the EGFR-inhibitor cetuximab - A report of 29 patients.	2009-10-03	19797039
In vitro activity of nadifloxacin against several Gram-positive bacteria and analysis of the possible evolution of resistance after 2 years of use in Germany.	2009-03	19095414
Simultaneous determination of (fluoro)quinolones antibacterials residues in bovine milk using ultra performance liquid chromatography-tandem mass spectrometry.	2009-02-20	19162423
[Effect of the admixture of tetracycline and nadifloxacin ointments on their stability and their antibacterial activity].	2008-08	18670189
A primer on topical antibiotics for the skin and eyes.	2008-04	18459527
Polyamidoamine (PAMAM) dendrimers as biocompatible carriers of quinolone antimicrobials: an in vitro study.	2007-07	17336426
[Therapy of severe cetuximab-induced acneiform eruptions with oral retinoid, topical antibiotic and topical corticosteroid].	2007-07	17146641
Antimicrobial susceptibility of strains of Propionibacterium acnes isolated from inflammatory acne.	2007-03-16	17357569
[Anti-microbial therapies for acne vulgaris: anti-inflammatory actions of anti-microbial drugs and their effectiveness].	2007-03-01	17380730
Nadifloxacin: a quinolone for topical treatment of skin infections and potential for systemic use of its active isomer, WCK 771.	2006-10	17020421
[Antibacterial activity of nadifloxacin against Staphylococcus and Propionibacterium isolated from patients with dermatological infections].	2006-08	17111596
Nadifloxacin downmodulates antigen-presenting functions of epidermal Langerhans cells and keratinocytes.	2006-05	16431082
Clinical and bacteriological evaluation of nadifloxacin 1% cream in patients with acne vulgaris: a double-blind, phase III comparison study versus erythromycin 2% cream.	2005-08-31	16436342
A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus.	2005-08-11	16078842
Nadifloxacin, an antiacne quinolone antimicrobial, inhibits the production of proinflammatory cytokines by human peripheral blood mononuclear cells and normal human keratinocytes.	2005-04	15795123
Modulation of androgen receptor transcriptional activity by anti-acne reagents.	2004-11	15519139
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.	2004-10	15452398
Susceptibility change to antibiotics of Staphylococcus aureus strains isolated from skin infections between July 1994 and November 2000.	2002-06	12111576
In vitro and in vivo antibacterial activity of T-3912, a novel non-fluorinated topical quinolone.	2002-03	11864945
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.	2001-09	11810583
Phenotypic and genotypic characterization of antibiotic-resistant Propionibacterium acnes isolated from acne patients attending dermatology clinics in Europe, the U.S.A., Japan and Australia.	2001-02	11251569
Current issues in antimicrobial therapy for the treatment of acne.	2001	11843235

Patents

Sample Use Guides

In Vivo Use Guide

a small amount of cream, gently massage it into the skin, and leave the area uncovered to allow any excess medication to evaporate

Route of Administration: Topical

In Vitro Use Guide

Nadifloxacin was active against all aerobic and anaerobic isolates. MIC(90) (MIC at which 90% of the isolates are inhibited) was 0.1 microg/ml for S. aureus, 0.78 microg/ml for both Streptococcus spp. and CNS, and 0.39 microg/ml for Propionibacterium spp

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:39:38 GMT 2025` Edited by `admin` on `Mon Mar 31 19:39:38 GMT 2025`
Record UNII	6CL9Y5YZEQ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ACUATIM

Preferred Name

English

Nadifloxacin

Official Name

English

Nadifloxacin [JAN]

Common Name

English

(±)-9-Fluoro-6,7-dihydro-8-(4-Hydroxypiperidino)-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid

Systematic Name

English

1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-

Systematic Name

English

OPC-7251

Code

English

OPC 7251

Code

English

Nadifloxacin [MI]

Common Name

English

Nadifloxacin [WHO-DD]

Common Name

English

Nadifloxacin [INN]

Common Name

English

NSC-759622

Code

English

1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (±)-

Common Name

English

Jinofloxacin

Common Name

English

Nadifloxacin [MART.]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D10AF05