C19H22F2N4O3

Base Information

• Chemical Name: C19H22F2N4O3
• CAS No.: 110871-86-8
• Molecular Formula: C19H22F2N4O3
• Molecular Weight: 392.405
• Hs Code.: 29339900
• Mol file: 110871-86-8.mol

Synonyms:C19H22F2N4O3;5-Amino-1-cyclopropyl-7-[(3S,5R)-3,5-dimethylpiperazin-4-ium-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylate

Chemical Property of C19H22F2N4O3

Chemical Property:

• Appearance/Colour: Light yellow powder
• Vapor Pressure: 4.2E-14mmHg at 25°C
• Melting Point: 265 °C
• Refractive Index: 1.611
• Boiling Point: 640.368 °C at 760 mmHg
• PKA: pKa1 6.25, pKa2 9.30(at 25℃)
• Flash Point: 341.082 °C
• PSA: 100.59000
• Density: 1.436 g/cm³
• LogP: 3.05660
• Storage Temp.: Store at 0-5°C
• Water Solubility.: Soluble in DMSO at 9mg/ml. Sparingly soluble in water
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 392.16599690
• Heavy Atom Count: 28
• Complexity: 685

Purity/Quality:

99% ^*data from raw suppliers

Sparfloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CN(CC([NH2+]1)C)C2=C(C(=C3C(=C2F)N(C=C(C3=O)C(=O)[O-])C4CC4)N)F
• Isomeric SMILES: C[C@@H]1CN(C[C@@H]([NH2+]1)C)C2=C(C(=C3C(=C2F)N(C=C(C3=O)C(=O)[O-])C4CC4)N)F
• Description: Sparfloxacin is the most potent fluoroquinolone antibiotic introduced for the treatment of community acquired infections. It has superior and broad in vitro activity against members of family Enterobacferiaceae and anaerobic bacteria, some of which are resistant toβ-lactam antibiotics or to aminoglycosides. In patients with surgical infections, sparfloxacin shows excellent activity against resistant pathogens. It is effective in treating patients with bladder irritability and is reported to have potential in the treatment of leprosy and Mycobacterium tuberculosis in mice. Favorable pharmacokinetic properties, good intracellular penetration and a lack of transferable resistance have been reported.
• Uses: antifungal A fluorianted quinolone antibacterial A fluorianted quinolone antibacterial.
• Therapeutic Function: Antibacterial
• Clinical Use: Sparfloxacin, (cis)-5-amino-1-cyclopropyl-7-(3,5-dimethyl)-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylicacid, is a newer fluoroquinolone.This compound exhibits higher potency against Grampositivebacteria, especially staphylococci and streptococci,than the fluoroquinolones currently marketed. It is also moreactive against chlamydia and the anaerobe Bacteroides fragilis.The activity of sparfloxacin against Gram-negative bacteriais also very impressive, and it compares favorably withciprofloxacin and ofloxacin in potency against Mycoplasmaspp., Legionella spp., Mycobacteria spp., and Listeria monocytogenes.Sparfloxacin has a long elimination half-life of18 hours, which permits once-a-day dosing for most indications.The drug is widely distributed into most fluidsand tissues. Effective concentrations of sparfloxacin areachieved for the treatment of skin and soft tissue infections,lower respiratory infections (including bronchitis and bacterialpneumonias), and pelvic inflammatory disease causedby gonorrhea and chlamydia. Sparfloxacin has also beenrecommended for the treatment of bacterial gastroenteritisand cholecystitis. The oral bioavailability of sparfloxacinis claimed to be good, and sufficient unchanged drug isexcreted to be effective for the treatment of urinary tract infections.Nearly 20% of an orally administered dose is excretedas an inactive glucuronide.

Technology Process of C19H22F2N4O3

There total 4 articles about C19H22F2N4O3 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: 63.0%

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (103772-14-1) + cis-2,6-dimethylpiperazine (21655-48-1,1013625-96-1) → sparfloxacin (110871-86-8)

Guidance literature:

With pyridine; at 80 ℃; for 0.666667h;

DOI:10.1021/jm00168a018

Reference yield:

1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester (107564-02-3) → sparfloxacin (110871-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / triethylamine / toluene / 1 h / Heating

2: 96 percent / acetic acid, aq. H₂SO₄ / 0.17 h / 100 °C

3: 63 percent / pyridine / 0.67 h / 80 °C

With pyridine; sulfuric acid; acetic acid; triethylamine; In toluene;

DOI:10.1021/jm00168a018

Reference yield:

ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate (110872-04-3) → sparfloxacin (110871-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / acetic acid, aq. H₂SO₄ / 0.17 h / 100 °C

2: 63 percent / pyridine / 0.67 h / 80 °C

With pyridine; sulfuric acid; acetic acid;

DOI:10.1021/jm00168a018

upstream raw materials:

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

cis-2,6-dimethylpiperazine

1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester

ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Downstream raw materials:

chrysin-ethylidene-sparfloxacin

Refernces

• 1、 Miyamoto, Teruyuki,Matsumoto, Jun-ichi,Chiba, Katsumi,Egawa, Hiroshi,Shibamori, Koh-ichiro,et al.. "Synthesis and Structure-Activity Relationships of 5-Substituted 6,8-Difluoroquinolones, Including Sparfloxacin, a New Quinolone Antibacterial Agent with Improved Potency". . p. 1645 - 1656. Retrieved 2007/10/02.