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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 of Nadifloxacin

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Current issues in antimicrobial therapy for the treatment of acne.
2001
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.
2001 Sep
In vitro and in vivo antibacterial activity of T-3912, a novel non-fluorinated topical quinolone.
2002 Mar
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.
2004 Oct
[Antibacterial activity of nadifloxacin against Staphylococcus and Propionibacterium isolated from patients with dermatological infections].
2006 Aug
Simultaneous determination of (fluoro)quinolones antibacterials residues in bovine milk using ultra performance liquid chromatography-tandem mass spectrometry.
2009 Feb 20
Topical nadifloxacin 1% cream vs. topical erythromycin 4% gel in the treatment of mild to moderate acne.
2010 Dec
A modified surgical technique for steatocystoma multiplex.
2010 Jan
Cetuximab-induced skin exanthema: Improvement by a reactive skin therapy.
2010 Sep-Oct
Patents

Patents

Sample Use Guides

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
Name Type Language
Nadifloxacin
INN   JAN   MART.   MI   WHO-DD  
INN  
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
ACUATIM
Brand 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
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Code System Code Type Description
FDA UNII
6CL9Y5YZEQ
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PRIMARY
DRUG BANK
DB12447
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CHEBI
31889
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WIKIPEDIA
Nadifloxacin
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INN
6702
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ChEMBL
CHEMBL363449
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SMS_ID
100000084408
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DRUG CENTRAL
1864
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PUBCHEM
4410
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MERCK INDEX
m7700
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PRIMARY Merck Index
EVMPD
SUB09110MIG
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CAS
124858-35-1
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NCI_THESAURUS
C166927
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EPA CompTox
DTXSID5046483
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NSC
759622
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