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)
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 | ( + / - ) |
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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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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Nadifloxacin downmodulates antigen-presenting functions of epidermal Langerhans cells and keratinocytes. | 2006 May |
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[Therapy of severe cetuximab-induced acneiform eruptions with oral retinoid, topical antibiotic and topical corticosteroid]. | 2007 Jul |
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[Effect of the admixture of tetracycline and nadifloxacin ointments on their stability and their antibacterial activity]. | 2008 Aug |
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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
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 19:14:28 GMT 2023
by
admin
on
Fri Dec 15 19:14:28 GMT 2023
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Record UNII |
6CL9Y5YZEQ
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Record Status |
Validated (UNII)
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D10AF05
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Nadifloxacin
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m7700
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SUB09110MIG
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124858-35-1
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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