Lomefloxacin

Base Information

• Chemical Name: Lomefloxacin
• CAS No.: 98079-51-7
• Molecular Formula: C17H19F2N3O3
• Molecular Weight: 387.814
• Hs Code.: 29419000
• UNII: L6BR2WJD8V
• DSSTox Substance ID: DTXSID4040680
• Nikkaji Number: J135.046C
• Wikipedia: Lomefloxacin
• Wikidata: Q203618
• NCI Thesaurus Code: C61814
• Metabolomics Workbench ID: 43230
• ChEMBL ID: CHEMBL561
• Mol file: 98079-51-7.mol

Synonyms:1-ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;Décalogiflox;Logiflox;lomefloxacin;lomefloxacin hydrochloride;lomenfloxacin;Maxaquin;NY 198;NY-198;Ocacin;Okacin;Okacyn;SC 4711;SC-4711

Chemical Property of Lomefloxacin

Chemical Property:

• Appearance/Colour: off-white to yellow crystals
• Vapor Pressure: 4.87E-14mmHg at 25°C
• Melting Point: 239-240 °C
• Refractive Index: 1.547
• Boiling Point: 542.7 °C at 760 mmHg
• PKA: -0.25±0.20(Predicted)
• Flash Point: 282 °C
• PSA: 74.57000
• Density: 1.342 g/cm³
• LogP: 2.99170
• Storage Temp.: −20°C
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 351.13944780
• Heavy Atom Count: 25
• Complexity: 586

Purity/Quality:

99% ^*data from raw suppliers

Lomefloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1C=C(C(=O)C2=CC(=C(C(=C21)F)N3CCNC(C3)C)F)C(=O)O
• Description: Lomefloxacin is a kind of fluoroquinolone antibiotics used for the treatment of bacterial infections such as bronchitis and urinary tract infection. It can also used to prevent the urinary tract infections prior surgery. It has bactericidal effect against a wide range of gram-negative and gram-positive organisms. It takes effect through interfering with the normal function of the bacteria enzyme DNA gyrase and topoisomerase IV, further inhibiting the transcription and replication of bacterial DNA. This effect results in strand breakage of bacterial chromosome, supercoiling and resealing, further causing bacteria death. Lomefloxacin is a once-daily, third-generation quinolone antibiotic useful in the treatment of bacterial infections. The new fluorinated quinolone does not interfere with the metabolism of theophylline; it is efficacious against pathogens resistant to cephalosporins, penicillins and aminoglycosides.
• Uses: Anti bacterial.
• Therapeutic Function: Antibacterial
• Clinical Use: 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (Maxaquin) is adifluorinated quinolone with a longer elimination half-life(7–8 hours) than other members of its class. It is the onlyquinolone for which once-daily oral dosing suffices. The oralbioavailability of lomefloxacin is estimated to be 95% to98%. Food slows, but does not prevent, its oral absorption.The extent of biotransformation of lomefloxacin is only about5%, and high concentrations of unchanged drug, rangingfrom 60% to 80%, are excreted in the urine. The comparativelylong half-life of lomefloxacin is apparently because ofits excellent tissue distribution and renal reabsorption and not because of plasma protein binding (only ～10%) or enterohepaticrecycling (biliary excretion is estimated to be ～10%).Lomefloxacin has been approved for two primary indications. First, it is indicated for acute bacterial exacerbations of chronic bronchitis caused by H. influenzae or Moraxella (Branhamella) catarrhalis, but not if Streptococcus pneumoniae is the causative organism. Second, it is used for prophylaxis of infection following transurethral surgery. Lomefloxacin also finds application in the treatment of acute cystitis and chronic urinary tract infections caused by Gram-negative bacilli.

Technology Process of Lomefloxacin

There total 6 articles about Lomefloxacin 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: 96.0%

(RS)-2-methylpiperazine (109-07-9) + ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (100501-62-0) → lomefloxacin (98079-51-7)

Guidance literature:

(RS)-2-methylpiperazine; ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate; With potassium carbonate; In water; at 90 - 95 ℃; for 10h;

With hydrogenchloride; water; at 20 ℃; for 3h; pH=7.5;

Reference yield: 89.0%

lomefloxacin hydrochloride ethyl ester → Lomefloxacin hydrochloride (98079-51-7,98079-52-8)

Guidance literature:

With sulfuric acid; acetic acid; In water; for 2h;

Reference yield: 85.0%

1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (75338-42-0) + (RS)-2-methylpiperazine (109-07-9) → lomefloxacin (98079-51-7)

Guidance literature:

In acetonitrile; Heating;

DOI:10.1021/jm00107a039

upstream raw materials:

1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

(RS)-2-methylpiperazine

ethyl 1-ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylate

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

Downstream raw materials:

7-(2-aminoethylamino)-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

8-Fluoro-9-(3-methyl-piperazin-1-yl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

8-desfluoro-lomefloxacin

8-chloro-1-ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid

Refernces

• 1、 -. "Preparation method of lomefloxacin hydrochloride". Paragraph 0025-0029. . Retrieved 2019/12/25.
• 2、 Hermecz, Istvan,Vasvari-Debreczy, Lelle,Podanyi, Benjamin,Kereszturi, Geza,Balogh, Maria,Horvath, Agnes,Varkonyi, Peter. "Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids". . p. 1111 - 1116. Retrieved 2007/10/03.