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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

Molecular Formula C19H21FN2O4
Molecular Weight 360.3794
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

PubMed

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
Record UNII
6CL9Y5YZEQ
Record Status Validated (UNII)
Record Version