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Temafloxacin

Temafloxacin structure

CAS No:
108319-06-8
Formula:
C21H18F3N3O3
Chemical Name:
Temafloxacin
Synonyms:
3-Quinolinecarboxylic acid,1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-;1-(2,4-Difluorophenyl)-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;Temafloxacin;T 1258;A 62254;(±)-Temafloxacin;Teflox;A 63004;Temac;108138-28-9
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid is a quinolone that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted at positions 1, 6, and 7 by 2,4-difluorophenyl, fluorine, and 3-methylpiperazin-1-yl groups, respectively. It is a quinolone, an amino acid, a monocarboxylic acid, an organofluorine compound, a secondary amino compound, a tertiary amino compound, a N-arylpiperazine and a quinolone antibiotic.|Temafloxacin is an antibiotic agent belonging to the fluoroquinolone drug class. It was first approved for use in the U.S. market in 1992, but was withdrawn shortly due to the reports of serious adverse reactions, such as allergic reactions and hemolyric anemia, resulting in three deaths.

Temafloxacin Basic Attributes

Molecular Weight：

417.38

Exact Mass：

417.38

DSSTox ID：

DTXSID7044132

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

72.9

XLogP3：

-0.2

Density：

1.3372 (estimate)

Boiling Point：

608.9ºC at 760mmHg

Flash Point：

322.1ºC

Refractive Index：

1.603

Toxicity

Toxicity Summary：

Severe allergic reactions and hemolytic anemia were observed during the first few months of use leading to fatalities and the drug's eventual withdrawal from the market.

Drug Information

Drug Indication：

For the treatment of lower respiratory tract infections, genital and urinary infections like prostatitis, and skin infections.

Pharmacology：

Temafloxacin is a fluoroquinolone antibiotic drug, marketed as Omniflox by Abbot Laboratories, which was withdrawn from the market in 1992 due to fatal adverse effects. 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.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

Absorption：

Studies in healthy volunteers indicate that the average bioavailability of temafloxacin exceeds 90%, with little intersubject variability.

Metabolism/Metabolites：

Hepatic.

Biological Half-Life：

Approximately 8 hours in patients with normal renal function.

Mechanism of Action：

The bactericidal action of temafloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.

MeSH Entry Terms：

1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(3-methyl-1-piperazinyl)quinoline-3-carboxylic acid, hydrochloride

Temafloxacin Use and Manufacturing

Antibacterial (microbial DNA topoisomerase inhibitor).

Computed Properties

Molecular Weight:417.4
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:3
Exact Mass:417.13002593
Monoisotopic Mass:417.13002593
Topological Polar Surface Area:72.9
Heavy Atom Count:30
Complexity:721
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Diethyl carbonate

1,2-Dimethoxyethane

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Temafloxacin

CAS No.: 108319-06-8

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