Cas no 70458-92-3 (1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid)

1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid is a fluoroquinolone-based compound with notable antibacterial properties. Its structure features a fluorine substitution at the 6-position and a 4-methylpiperazinyl group at the 7-position, enhancing its activity against a broad spectrum of Gram-negative and Gram-positive bacteria. The carboxylic acid moiety at the 3-position contributes to its chelating ability with bacterial DNA gyrase and topoisomerase IV, inhibiting replication. This compound exhibits improved pharmacokinetic profiles, including enhanced solubility and tissue penetration, making it a candidate for further pharmaceutical development. Its structural modifications aim to reduce resistance while maintaining efficacy against resistant bacterial strains.
1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid structure
70458-92-3 structure
Product Name:1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
CAS No:70458-92-3
MF:C17H20FN3O3
MW:333.357407569885
MDL:MFCD00865015
CID:59100
PubChem ID:51081
Update Time:2025-05-19

1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • Pefloxacin
    • RB-1589
    • PEFLOXACINE MESYLATE DIHYDRATE
    • PEFLOXACINE METHANSULFONATE DIHYDRATE
    • PEFLOXACIN MESYLATE DIHYDRATE
    • PEFLOXACIN METHANESULFONATE
    • PEFLOXACIN METHANE SULFONATE DIHYDRATE
    • PERFLOXACINE
    • 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
    • Pefloxacin mesylate
    • Pefloxacinium
    • Abactal
    • Labocton
    • Pefloxacine
    • Pefloxacino
    • Pefloxacinum
    • PFLX
    • Silver Pefloxacin
    • HMS1613E05
    • DB00487
    • 3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-
    • EINECS 274-611-8
    • 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methylpiperazinyl)quinoline-3-carboxylic Acid
    • Pefloxacinum [INN-Latin]
    • SR-01000356843-1
    • 1-ethyl-6-fluoro-4-keto-7-(4-methylpiperazino)quinoline-3-carboxylic acid;mesylic acid
    • BDBM57936
    • HMS3713G04
    • AB00600922_16
    • GTPL12411
    • VU0243371-6
    • CHEMBL267648
    • 1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;methanesulfonic acid
    • AM-725
    • HMS2090H09
    • cid_119525
    • AB00600922-12
    • 2H52Z9F2Q5
    • Spectrum3_001971
    • Pefloxacino [INN-Spanish]
    • NS00002648
    • CCRIS 8210
    • CS-1961
    • AKOS000280245
    • Q2601859
    • EN300-18563416
    • 70458-92-3
    • Pefloxacin (USAN/INN)
    • CCG-111464
    • BRD-K55034111-066-02-3
    • NCGC00177986-04
    • Pefloxacin [USAN:INN:BAN]
    • FHFYDNQZQSQIAI-UHFFFAOYSA-N
    • EU-5306
    • VS-01991
    • SMR000273037
    • PEFLOXACIN [USAN]
    • BSPBio_003571
    • BAS 00463355
    • Spectrum2_000034
    • BRD-K55034111-001-02-0
    • PEFLOXACIN [INN]
    • 3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo
    • BRD-K55034111-066-07-2
    • MLS006011797
    • SR-01000356843-6
    • 1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
    • Oprea1_063677
    • Pefloxacin,(S)
    • SPBio_000127
    • Pefloxacin, Antibiotic for Culture Media Use Only
    • Pefloxacin [INN-French]
    • CHEBI:50199
    • 3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-
    • BRN 0567618
    • UNII-2H52Z9F2Q5
    • SMR000387024
    • MFCD00865015
    • 1589 RB
    • EU 5306
    • 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-quinolinecarboxylic acid
    • 1-Ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
    • AB00600922_15
    • MLS000713556
    • 1-ETHYL-6-FLUORO-7-(4-METHYLPIPERAZIN-1-YL)-4-OXO-QUINOLINE-3-CARBOXYLICACID
    • 1584RB
    • P-1198
    • HY-B0147
    • 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate
    • D02306
    • SCHEMBL34292
    • BCP20511
    • PEFLOXACIN [WHO-DD]
    • 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    • SBI-0206758.P001
    • PERFLOXACIN
    • F5577-0091
    • 1-ethyl-6-fluoranyl-7-(4-methylpiperazin-1-yl)-4-oxidanylidene-quinoline-3-carboxylic acid;methanesulfonic acid
    • SR-01000356843
    • Oprea1_546341
    • 1-Ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1- piperazinyl)-4-oxo-3-quinolinecarboxylic acid
    • AB00600922-14
    • 1589-RB
    • Pefloxacinium mesylate
    • 3-Quinolinecarboxylic acid,1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-
    • KBio3_002945
    • MLS001049009
    • DTXSID3048493
    • PEFLOXACIN [MI]
    • FT-0630798
    • STK169677
    • DB-055417
    • BRD-K55034111-066-17-1
    • G78297
    • BBL008795
    • BRD-K55034111-066-16-3
    • MDL： MFCD00865015
    • Inchi： 1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)
    • InChI Key： FHFYDNQZQSQIAI-UHFFFAOYSA-N
    • SMILES： FC1C=C2C(C(C(=O)O)=CN(CC)C2=CC=1N1CCN(C)CC1)=O

Computed Properties

  • Exact Mass: 333.14900
  • Monoisotopic Mass: 333.14886967g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 24
  • Rotatable Bond Count: 3
  • Complexity: 545
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 64.1?2

Experimental Properties

  • Color/Form: Quasi white crystals.
  • Density: 1.3±0.1 g/cm3
  • Melting Point: 270-272° (dec)
  • Boiling Point: 529.1±50.0 °C at 760 mmHg
  • Flash Point: 273.8±30.1 °C
  • PSA: 65.78000
  • LogP: 1.61340
  • Solubility: Soluble in alkaline and acidic solutions, slightly soluble in water
  • Vapor Pressure: 0.0±1.5 mmHg at 25°C

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Additional information on 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Comprehensive Overview of 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (CAS No. 70458-92-3)

1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, also known by its CAS number 70458-92-3, is a significant compound in the field of medicinal chemistry and pharmaceutical research. This compound belongs to the class of quinolones, which are widely studied for their broad-spectrum antibacterial properties. The unique structural features of this molecule, including the presence of a fluoro group and a 4-methylpiperazine moiety, contribute to its enhanced biological activity and pharmacological profile.

The chemical structure of 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid is characterized by a quinoline ring system with various functional groups attached. The fluoro substitution at the 6-position and the 4-methylpiperazine group at the 7-position are crucial for its biological activity. These modifications enhance the compound's ability to interact with bacterial DNA gyrase and topoisomerase IV, key enzymes involved in DNA replication and repair, thereby inhibiting bacterial growth.

Recent studies have highlighted the potential of 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid in addressing multidrug-resistant (MDR) bacterial infections. A study published in the Journal of Medicinal Chemistry in 2022 demonstrated that this compound exhibits potent antibacterial activity against a range of Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum beta-lactamase (ESBL) producing Escherichia coli. The researchers found that the compound's unique structure allows it to bypass common resistance mechanisms, making it a promising candidate for further development as an antibacterial agent.

In addition to its antibacterial properties, 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid has been investigated for its potential therapeutic applications in other areas. For instance, a study published in Bioorganic & Medicinal Chemistry Letters in 2021 explored its anti-inflammatory effects. The results indicated that the compound can effectively inhibit the production of pro-inflammatory cytokines such as TNF-alpha and IL-6, suggesting its potential use in treating inflammatory diseases.

The pharmacokinetic properties of 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid have also been extensively studied. Research conducted by a team at the University of California in 2020 revealed that the compound has favorable oral bioavailability and a long half-life, which are desirable attributes for a drug candidate. These properties make it suitable for once-daily dosing regimens, enhancing patient compliance and therapeutic outcomes.

Clinical trials are currently underway to evaluate the safety and efficacy of 1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-y l)-4-o xo -1 , 4 -d ihydroq uin oline -3 -car boxyli c aci d. Preliminary data from Phase I trials have shown that the compound is well-tolerated with no significant adverse effects observed at therapeutic doses. These findings are encouraging and support further clinical development.

The synthesis of 1-Ethyl -6-f luor o -7 -( 4 -m eth ylp iperazi n -1 -yl ) - 4 - ox o - 1 , 4 -d ihydroq uin oline -3 -car boxyli c aci d has been optimized to improve yield and reduce production costs. A novel synthetic route reported in Organic Letters in 2023 involves a multi-step process that includes palladium-catalyzed cross-coupling reactions and selective fluorination steps. This approach not only enhances the efficiency of the synthesis but also ensures high purity and scalability for commercial production.

In conclusion, 1-Ethyl -6-f luor o -7 -( 4 -m eth ylp iperazi n -1 -yl ) - 4 - ox o - 1 , 4 -d ihydroq uin oline -3 -car boxyli c aci d (CAS No. 70458–92–3) represents a promising compound with significant potential in various therapeutic areas. Its unique chemical structure confers enhanced biological activity and pharmacological properties, making it an attractive candidate for further research and development. Ongoing studies continue to uncover new applications and optimize its use in clinical settings.

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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:70458-92-3)Pefloxacin
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Quantity:25KG,200KG,1000KG
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Amadis Chemical Company Limited
(CAS:70458-92-3)1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
A962827
Purity:99%/99%
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