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

• ChemBase ID: 370
• Molecular Formular: C17H20FN3O3
• Molecular Mass: 333.3574032
• Monoisotopic Mass: 333.14886974
• SMILES: Fc1c(N2CCN(CC2)C)cc2n(CC)cc(c(=O)c2c1)C(=O)O
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1cc(N1CCN(CC1)C)c(c2)F
• InChI: 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)
• InChIKey: FHFYDNQZQSQIAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: pefloxacin
• Brand Name: PFLX; Pefloxacin mesylate; Pefloxacin methanesulfonate; Pefloxacin [INN-French]; Pefloxacine; Pefloxacino [INN-Spanish]; Pefloxacinum [INN-Latin]
• Synonyms: Pefloxacin

Database IDs

• CAS Number: 70458-92-3
• PubChem SID: 160963833; 46507338
• PubChem CID: 51081

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.6647615
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.72274345
• LogD (pH = 7.4): 0.16012752
• Log P: 0.8768126
• Molar Refractivity: 90.7715 cm^3
• Polarizability: 32.979492 Å^3
• Polar Surface Area: 64.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.2
• LOG S: -2.43
• Solubility (Water): 1.23e+00 g/l

PROPERTIES

Physical Property

• Solubility: 11.4 mg/mL at 25 oC
• Hydrophobicity(logP): 2.4

DETAILS

DrugBank - DB00487

• Drug Groups: approved
• Description: A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria. [PubChem]
• Indication: For the treatment of uncomplicated gonococcal urethritis in males and for gram-negative-bacterial infections in the gastrointestinal system and the genitourinary tract.
• Pharmacology: Pefloxacin is a fluoroquinolone antibiotic. Flouroquinolones such as pefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.
• Toxicity: Adverse reactions include peripheral neuropathy, nervousness, agitation, anxiety, and phototoxic events (rash, itching, burning) due to sunlight exposure.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic. Primary metabolites are pefloxacin N-oxide and norfloxacin.
• Absorption: Well absorbed by the oral route.
• Half Life: 8.6 hours
• Protein Binding: 20-30%
• External Links: Wikipedia