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
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)
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/15795123Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/15452398
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 |
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Target ID: CHEMBL3038482 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11810583 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Current issues in antimicrobial therapy for the treatment of acne. | 2001 |
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Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus. | 2001 Sep |
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In vitro and in vivo antibacterial activity of T-3912, a novel non-fluorinated topical quinolone. | 2002 Mar |
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Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections. | 2004 Oct |
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[Antibacterial activity of nadifloxacin against Staphylococcus and Propionibacterium isolated from patients with dermatological infections]. | 2006 Aug |
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Simultaneous determination of (fluoro)quinolones antibacterials residues in bovine milk using ultra performance liquid chromatography-tandem mass spectrometry. | 2009 Feb 20 |
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Topical nadifloxacin 1% cream vs. topical erythromycin 4% gel in the treatment of mild to moderate acne. | 2010 Dec |
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A modified surgical technique for steatocystoma multiplex. | 2010 Jan |
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Cetuximab-induced skin exanthema: Improvement by a reactive skin therapy. | 2010 Sep-Oct |
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/15452398
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
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D10AF05
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124858-35-1
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ACTIVE MOIETY