CID 6956357

Base Information

• Chemical Name: CID 6956357
• CAS No.: 100986-85-4
• Molecular Formula: C18H20FN3O4
• Molecular Weight: 361.373
• Hs Code.: 29349990
• Mol file: 100986-85-4.mol

Synonyms:

Chemical Property of CID 6956357

Chemical Property:

• Appearance/Colour: Slight yellow powder
• Vapor Pressure: 6.7E-14mmHg at 25°C
• Melting Point: 218 °C
• Refractive Index: 1.669
• Boiling Point: 571.495 °C at 760 mmHg
• PKA: 5.19±0.40(Predicted)
• Flash Point: 299.43 °C
• PSA: 75.01000
• Density: 1.48 g/cm³
• LogP: 1.54690
• Storage Temp.: Store at 0-5°C
• Sensitive.: Light Sensitive
• Solubility.: chloroform: soluble10mg/mL
• Water Solubility.: Slightly soluble in water or methanol. Soluble in glacial acetic acid or dichloromethane
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 361.14378429
• Heavy Atom Count: 26
• Complexity: 628

Purity/Quality:

99% ^*data from raw suppliers

Levofloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-42/43-68-20/21/22-64-63
• Safety Statements: 26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CC[NH+](CC4)C)F)C(=O)[O-]
• Isomeric SMILES: C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CC[NH+](CC4)C)F)C(=O)[O-]
• Description: Levofloxacin, the optically active S-isomer of the fluoroquinolone antibiotic ofloxacin, is two to four times more potent than ofloxacin with reportedly less side effects in treating infections of the lower respiratory and urinary tract, prostate infections and sexually transmitted diseases. It has broad and potent antibacterial activity over common Grampositive and -negative aerobic pathogens and obligate anaerobes. Different from the cephem antibiotics, levofloxacin is unique in its marked selectivity against members of the family Enterobacteriaceae and its negligible effect on predominant anaerobes. Levofloxacin also exhibits satisfactory antimicrobial effects in surgical infections and it may be used for treatment of gastrointestinal infections such as traveler’s diarrhea associated with the pathogenic Enterobacteriaceae.
• Uses: Levofloxacin is a broad-spectrum antibiotic used in pharmacokinetic?, antibiotic resistance?, and resistance prevention?studies. Levofloxacin is active against Gram-positive and Gram-negative bacteria. It inhibits DNA gyrase (type II topoisomerase) and topoisomerase IV, thereby inhibiting cell division. Antibacterial.
• Therapeutic Function: Antibacterial
• Clinical Use: Acute bacterial sinusitis Acute bacterial exacerbations of chronic bronchitis, community-acquired pneumonia Uncomplicated and complicated skin and skin structure infections Uncomplicated and complicated urinary infections including acute pyelonephritis Chronic bacterial prostatitis
• Drug interactions: Potentially hazardous interactions with other drugs Aminophylline and theophylline: possibly increased risk of convulsions. Analgesics: possibly increased risk of convulsions with NSAIDs. Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone - avoid. Anticoagulants: anticoagulant effect of coumarins and phenindione enhanced. Antimalarials: manufacturer advises avoid concomitant use with artemether and lumefantrine. Ciclosporin: half-life of ciclosporin increased by 33%; increased risk of nephrotoxicity. Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide. Tacrolimus: may increase tacrolimus concentration.

Technology Process of CID 6956357

There total 34 articles about CID 6956357 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: 97.1%

1-methyl-piperazine (109-01-3) + levofloxacin Q-acid (100986-89-8) → levofloxacin (100986-85-4,83380-47-6)

Guidance literature:

With potassium hydroxide; In water; at 55 ℃; for 24h; Reagent/catalyst; Time; Temperature; Solvent;

Reference yield: 92.0%

N-methylpiperazine dihydrochloride (50398-09-9,51545-09-6,34352-59-5) + levofloxacin Q-acid (100986-89-8) → levofloxacin (100986-85-4,83380-47-6)

Guidance literature:

N-methylpiperazine dihydrochloride; levofloxacin Q-acid; With boron trifluoride-tetrahydrofuran complex; triethylamine; In acetonitrile; at 20 ℃; for 24.5h;

With methanol; for 24h; Reflux;

In ethanol; at 20 ℃; for 16h;

Reference yield: 85.7%

1-methyl-piperazine (109-01-3) + ethyl (S)-(-)-9,10-Difluoro-3-Methyl-7-Oxo-2,3-Dihydro-7H-Pyrido[1,2,3-de]-[1,4]Benzoxazine-6-Carboxylate (106939-34-8) → levofloxacin (100986-85-4,83380-47-6)

Guidance literature:

With acetic acid; In water; N,N-dimethyl-formamide; at 70 - 105 ℃; for 10h; Temperature; Solvent; Reagent/catalyst;

upstream raw materials:

1-methyl-piperazine

(-)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid BF2-chelate

levofloxacin Q-acid

ofloxacin

Refernces

• 1、 Jiao, Feipeng,Yang, Weijie,Wang, Fen,Tian, Lingxing,Li, Lin,Chen, Xiaoqing,Mu, Kelang. "Enantioseparation of racemic mixtures based on solvent sublation". . p. 661 - 667. Retrieved 2012.
• 2、 Pal, Suman,Ramu, Vadde,Taye, Nandaraj,Mogare, Devraj G.,Yeware, Amar M.,Sarkar, Dhiman,Reddy, D. Srinivasa,Chattopadhyay, Samit,Das, Amitava. "GSH Induced Controlled Release of Levofloxacin from a Purpose-Built Prodrug: Luminescence Response for Probing the Drug Release in Escherichia coli and Staphylococcus aureus". . p. 2062 - 2070. Retrieved 2016.
• 3、 Zhao, Baojing,Li, Lan,Wang, Yuting,Zhou, Zhiming. "Preparation of polar group derivative β-cyclodextrin bonded hydride silica chiral stationary phases and their chromatography separation performances". . p. 643 - 649. Retrieved 2019.
• 4、 Nakhaei, Ahmad,Ramezani, Shirin,Shams-Najafi, Sayyed Jalal,Farsinejad, Sadaf. "Nano-Fe3 O4@ZrO2-SO3 H as highly efficient recyclable catalyst for the green synthesis of fluoroquinolones". . p. 739 - 746. Retrieved 2018.
• 5、 Ali, Imran,Suhail, Mohd,Asnin, Leonid. "Chiral separation and modeling of quinolones on teicoplanin macrocyclic glycopeptide antibiotics CSP". . p. 1304 - 1311. Retrieved 2018.
• 6、 Tian, Lingxing,Yang, Weijie,Chen, Xiaoqing,Xie, Yixi. "Enantioselective extraction of racemic ofloxacin by di(2-ethylhexyl) phosphoric acid and tartaric acid derivatives as mixed complex chiral selectors". . p. 642 - 645. Retrieved 2011.
• 7、 Li, Ling,Xue, Xuqi,Zhang, Huige,Lv, Wenjuan,Qi, Shengda,Du, Hongying,Manyande, Anne,Chen, Hongli. "In-situ and one-step preparation of protein film in capillary column for open tubular capillary electrochromatography enantioseparation". . p. 2139 - 2142. Retrieved 2021.
• 8、 -. "Preparation method of levofloxacin and intermediates thereof". . . Retrieved 2021/03/30.