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Temafloxacin

HCID 60021
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
108319-06-8
Standard-SMILES
CC1CN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)CCN1
InChIKey
QKDHBVNJCZBTMR-UHFFFAOYSA-N
Summenformel
C21H18F3N3O3
Durchschnittliche Molmasse
417,4 g/mol
Monoisotopische Masse
417,13002593

Überblick

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, a monocarboxylic acid, an amino acid, an organofluorine compound, a N-arylpiperazine, a secondary amino compound, a tertiary amino compound and a quinolone antibiotic.

Namen und Bezeichner

Bevorzugter Name
Temafloxacin
IUPAC
1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
Englischer Name
TEMAFLOXACIN
Summenformel
C21H18F3N3O3
Molmasse
417.38

Namen und Synonyme

Temafloxacin108319-06-8TemafloxacineOmnifloxTemafloxacinum1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidA 62254TemafloxacinoDTXSID7044132T 1258A-622541WZ12GTT67
Weitere Namen anzeigen
TefloxA-63004AKOS 92085TeMafloxacin HClTEMAFLOXACIN USP/EP/BPTemafloxacin (Omniflox)6-Fluoro-1-(2,4-difluorophenyl)-7-(3-methylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
DTXCID5024132RefChem:891341CHEBI:77788J01MA05(+-)-1-(2,4-DIFLUOROPHENYL)-6-FLUORO-1,4-DIHYDRO-7-(3-METHYL-1-PIPERAZINYL)-4-OXO-3-QUINOLINECARBOXYLIC ACIDAbbott 62254MFCD008648281-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

Datenbank-Bezeichner

CAS
108319-06-8
PubChem CID
60021
DTXSID
DTXSID7044132
ChEMBL
CHEMBL277100
ChEBI
CHEBI:77796
UNII
1WZ12GTT67
Nikkaji
J345.988H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,6
Polarare Oberfläche (TPSA)
72,9 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
3
Schwere Atome
30
Formalladung
0
Komplexität
721

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use

Pharmaceuticals -> Antibiotics

Collision Cross Section193.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7044132]

Physikochemische Eigenschaften

Schmelzpunkt
200 °C · >200°C (dec.)
Siedepunkt
608.9 · 608.9±55.0 °C(Predicted)
Dichte
1.3372 · 1.3372 (estimate)
storage temp.
2 · 2-8°C(protect from light)
Löslichkeit
Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
6.02 · 6.02±0.41(Predicted)
Farbe
White to Off-White
Stabilität
Hygroscopic
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
SMILES
N1(C2=CC=C(F)C=C2F)C2=C(C=C(F)C(N3CCNC(C)C3)=C2)C(=O)C(C(O)=O)=C1

Sicherheit und Regulatorisches

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Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

temafloxacin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Pharmacodynamics · 1 Eintrag

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 <i>E.coli</i> and <i>Neisseria gonorrhoea</i> as well as gram-positive bacteria including <i>S. pneumoniae</i> and <i>Staphylococcus aureus</i>. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.

Mechanism of Action · 1 Eintrag

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.

Biological Half-LifeApproximately 8 hours in patients with normal renal function.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification · 2 Einträge

Substances that inhibit the growth or reproduction of BACTERIA.

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.

Absorption, Distribution and ExcretionStudies in healthy volunteers indicate that the average bioavailability of temafloxacin exceeds 90%, with little intersubject variability.
Anwendungen · 2 Einträge

BeschreibungTemafloxacin is a fluoroquinolone antibiotic that acts as a DNA topoisomerase inhibitor. It has broad antimicrobial activity against gram-positive and gram-negative bacteria, such as S. pneumoniae, M. hominis, and anaerobic bacteria, including B. fragilis.

VerwendenTemafloxacin is an antimicrobial quinolone drug.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Natriumhydrid2-Methylpiperazin2,4-Dichloro-5-fluoroacetophenone2,4-DifluoranilinDiethylcarbonat1,2-Dimethoxy-ethan

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