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

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
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.
2004 Oct
Nadifloxacin downmodulates antigen-presenting functions of epidermal Langerhans cells and keratinocytes.
2006 May
[Therapy of severe cetuximab-induced acneiform eruptions with oral retinoid, topical antibiotic and topical corticosteroid].
2007 Jul
[Effect of the admixture of tetracycline and nadifloxacin ointments on their stability and their antibacterial activity].
2008 Aug
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:14:28 GMT 2023
Edited
by admin
on Fri Dec 15 19:14:28 GMT 2023
Record UNII
6CL9Y5YZEQ
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
Code System Code Type Description
FDA UNII
6CL9Y5YZEQ
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
DRUG BANK
DB12447
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
CHEBI
31889
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
WIKIPEDIA
Nadifloxacin
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
INN
6702
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL363449
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
SMS_ID
100000084408
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
DRUG CENTRAL
1864
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
PUBCHEM
4410
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
MERCK INDEX
m7700
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY Merck Index
EVMPD
SUB09110MIG
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
CAS
124858-35-1
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
NCI_THESAURUS
C166927
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID5046483
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
NSC
759622
Created by admin on Fri Dec 15 19:14:28 GMT 2023 , Edited by admin on Fri Dec 15 19:14:28 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY