Nadifloxacin

Base Information

• Chemical Name: Nadifloxacin
• CAS No.: 124858-35-1
• Deprecated CAS: 81962-84-7
• Molecular Formula: C19H21FN2O4
• Molecular Weight: 360.385
• European Community (EC) Number: 638-863-6
• NSC Number: 759622
• UNII: 6CL9Y5YZEQ
• DSSTox Substance ID: DTXSID5046483
• Nikkaji Number: J355.028A
• Wikipedia: Nadifloxacin
• Wikidata: Q426605
• NCI Thesaurus Code: C166927
• Metabolomics Workbench ID: 144343
• ChEMBL ID: CHEMBL363449
• Mol file: 124858-35-1.mol

Synonyms:9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidyl)-5-methyl-1-oxo-1H,5H-benzo(i,j)quinolizine-2-carboxylic acid;nadifloxacin;OPC 7251;OPC-7251;R-NDFX;S-NDFX

Chemical Property of Nadifloxacin

Chemical Property:

• Appearance/Colour: off-white crystalline solid
• Vapor Pressure: 1.77E-16mmHg at 25°C
• Melting Point: 245-247 °C
• Refractive Index: 1.668
• Boiling Point: 624.891 °C at 760 mmHg
• PKA: 5.55±0.40(Predicted)
• Flash Point: 331.722 °C
• PSA: 82.77000
• Density: 1.467 g/cm³
• LogP: 2.37210
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Sparingly, Heated)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 360.14853532
• Heavy Atom Count: 26
• Complexity: 631

Purity/Quality:

99% ^*data from raw suppliers

Nadifloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=C3N1C=C(C(=O)C3=CC(=C2N4CCC(CC4)O)F)C(=O)O
• Recent ClinicalTrials: Dalacin-T Gel Post Approval Study
• Recent NIPH Clinical Trials: Quantitative Determination of Nadifloxacin in Follicles of Acne Patients Treated by Topical Nadifloxacin With or Without Adapalene and Benzoyl Peroxide
• Description: Nadifloxacin is a fluoroquinolone antibiotic that is used topically. It is effective against the Gram-positive bacteria S. aureus and P. acnes, as well as Gram-negative bacteria. Nadifloxacin, one of the three new fluoroquinolone antibiotics launched in 1993 is indicated for topical treatment of acne vulgaris and other skin infections. Nadifloxacin has a potent and broad spectrum of activity against aerobic Gram-positive and -negative bacteria and against anaerobic bacteria. It produces significant improvement in patients with Propionibacterium acnes infection and does not appear to cause cross-resistance to other antibiotic agents. Its potent antimicrobial activity has also been demonstrated in the Pseudomonas aeruginosa burn wound infection model in mice. Nadifloxacin exerts its antibiotic activity by inhibiting the formation of supercoiled DNA by DNA gyrase.
• Uses: Fluorinated quinolone antibacterial (topical). Fluorinated quinolone antibacterial (topical) Calcium salt of polyacrylic acid crosslinked with divinyl glycol

Technology Process of Nadifloxacin

There total 5 articles about Nadifloxacin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 25.0%

4-HYDROXYPIPERIDINE (5382-16-1) + 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid (77483-92-2) → nadifloxacin (124858-35-1,81962-84-7)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; at 160 ℃; for 7h;

DOI:10.1248/cpb.37.2103

Reference yield:

6-fluoro-2-methyl-quinoline (1128-61-6) → nadifloxacin (124858-35-1,81962-84-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / Br₂, Ag₂SO₄, cc H₂SO₄, / 1 h

2: 68 percent / H₂, / PtO₂, / acetic acid / Ambient temperature

3: 2.) PPA, 3.) cc HCl, / 1.) 150 deg C, 1 h, 2.) 150 deg C, 30 min, 3.) AcOH, H₂O, reflux, 2 h,

4: 25 percent / hexamethylphosphoric acid triamide / 7 h / 160 °C

With hydrogenchloride; sulfuric acid; hydrogen; bromine; silver sulfate; platinum(IV) oxide; In N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid;

DOI:10.1248/cpb.37.2103

Reference yield:

5-bromo-6-fluoro-2-methylquinoline (80290-18-2) → nadifloxacin (124858-35-1,81962-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / H₂, / PtO₂, / acetic acid / Ambient temperature

2: 2.) PPA, 3.) cc HCl, / 1.) 150 deg C, 1 h, 2.) 150 deg C, 30 min, 3.) AcOH, H₂O, reflux, 2 h,

3: 25 percent / hexamethylphosphoric acid triamide / 7 h / 160 °C

With hydrogenchloride; hydrogen; platinum(IV) oxide; In N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid;

DOI:10.1248/cpb.37.2103

upstream raw materials:

4-HYDROXYPIPERIDINE

9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

6-fluoro-2-methyl-quinoline

5-bromo-6-fluoro-2-methylquinoline

Downstream raw materials:

R-(+)-9-fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid

S-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid

C₄₄H₄₅FN₂O₅S

Refernces

• 1、 -. "Pyrroloquinoline and benzoquinolizine compounds and antimicrobial compositions". . . Retrieved 2008/06/13.