1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 1214
• Molecular Formular: C21H18F3N3O3
• Molecular Mass: 417.3811296
• Monoisotopic Mass: 417.13002611
• SMILES: Fc1c(N2CC(NCC2)C)cc2n(cc(c(=O)c2c1)C(=O)O)c1c(F)cc(F)cc1
• Canonical SMILES: CC1NCCN(C1)c1cc2n(cc(c(=O)c2cc1F)C(=O)O)c1ccc(cc1F)F
• InChI: InChI=1S/C21H18F3N3O3/c1-11-9-26(5-4-25-11)19-8-18-13(7-16(19)24)20(28)14(21(29)30)10-27(18)17-3-2-12(22)6-15(17)23/h2-3,6-8,10-11,25H,4-5,9H2,1H3,(H,29,30)
• InChIKey: QKDHBVNJCZBTMR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: temafloxacin hcl; temafloxacin
• Brand Name: Omniflox
• Synonyms: Temafloxacin hydrochloride; Temafloxacina [spanish]; Temafloxacine [french]; Temafloxacinum [latin]; Temafloxacin

Database IDs

• CAS Number: 108319-06-8
• PubChem SID: 160964674; 46508032
• PubChem CID: 60021

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.6024737
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.82024103
• LogD (pH = 7.4): 1.0817627
• Log P: 1.0832037
• Molar Refractivity: 104.5341 cm^3
• Polarizability: 38.341084 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.94
• LOG S: -4.46
• Solubility (Water): 1.44e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.20 [BIOBYTE (1995)]

Product Information

• Purity: 97%

DETAILS

DrugBank - DB01405

• Drug Groups: withdrawn
• Description: Temafloxacin is a fluoroquinolone antibiotic drug which was withdrawn from sale in the U.S. shortly after its approval in 1992 because of serious adverse reactions resulting in three deaths. [Wikipedia]
• Indication: For the treatment of lower respiratory tract infections, genital and urinary infections like prostatitis, and skin infections.
• Pharmacology: Temafloxacin (marketed by Abbott Laboratories as Omniflox), is a fluoroquinolone antibiotic drug which was withdrawn from sale in the U.S. shortly after its approval in 1992 because of serious adverse reactions resulting in three deaths. Flouroquinolones such as lomefloxacin 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: Severe adverse reactions, including allergic reactions and hemolytic anemia, developed in about fifty patients during the first four months of its use, leading to three patient deaths
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic.
• Absorption: Studies in healthy volunteers indicate that the average bioavailability of temafloxacin exceeds 90%, with little intersubject variability.
• Half Life: Approximately 8 hours in patients with normal renal function.
• External Links: Wikipedia