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1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
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ChemBase ID:
1214
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Molecular Formular:
C21H18F3N3O3
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Molecular Mass:
417.3811296
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Monoisotopic Mass:
417.13002611
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SMILES and InChIs
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
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Cite this record
CBID:1214 http://www.chembase.cn/molecule-1214.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
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IUPAC Traditional name
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temafloxacin hcl
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temafloxacin
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Brand Name
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Synonyms
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Temafloxacin hydrochloride
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Temafloxacina [spanish]
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Temafloxacine [french]
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Temafloxacinum [latin]
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Temafloxacin
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CAS Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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5.6024737
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H Acceptors
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6
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H Donor
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2
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LogD (pH = 5.5)
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0.82024103
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LogD (pH = 7.4)
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1.0817627
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Log P
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1.0832037
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Molar Refractivity
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104.5341 cm3
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Polarizability
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38.341084 Å3
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Polar Surface Area
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72.88 Å2
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Rotatable Bonds
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3
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Lipinski's Rule of Five
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true
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Log P
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0.94
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LOG S
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-4.46
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Solubility (Water)
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1.44e-02 g/l
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PROPERTIES
PROPERTIES
Physical Property
Product Information
Bioassay(PubChem)
Hydrophobicity(logP)
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-0.20 [BIOBYTE (1995)]
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Show
data source
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Purity
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97%
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Show
data source
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DETAILS
DETAILS
DrugBank
DrugBank -
DB01405
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Item |
Information |
Drug Groups
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withdrawn |
Description
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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 |
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Enteric bacteria and other eubacteria |
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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 |
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PATENTS
PATENTS
PubChem Patent
Google Patent