Gatifloxacin
Grundinformationen
- CAS
112811-59-3- Standard-SMILES
COc1c(N2CCNC(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12- InChIKey
XUBOMFCQGDBHNK-UHFFFAOYSA-N- Summenformel
- C19H22FN3O4
- Durchschnittliche Molmasse
- 375,4 g/mol
- Monoisotopische Masse
- 375,1594344
Überblick
Gatifloxacin is a monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes. It has a role as an antimicrobial agent, an antiinfective agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a quinolone, a quinolinemonocarboxylic acid, an organofluorine compound, a N-arylpiperazine and a quinolone antibiotic.
Namen und Bezeichner
- Bevorzugter Name
- Gatifloxacin
- IUPAC
- 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
- Englischer Name
- Gatifloxacin
- Summenformel
- C19H22FN3O4
- Molmasse
- 375.39
Namen und Synonyme
Gatifloxacin112811-59-3TequinGatifloZymarAM-1155GatifloxacineZymaxidZymergatifloxacin anhydrousAM 11553-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-
Weitere Namen anzeigen
CG5501S)-AHPCGatiquinPD135432PD 135432PD-135432)BMS-206584GASTRODINUM
gatifloxacinoDTXSID50457041-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidgatifloxacinumPD-1354321-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidNSC-758701CHEBI:5280
Datenbank-Bezeichner
- CAS
112811-59-3- PubChem CID
- 5379
- DTXSID
DTXSID5045704- ChEMBL
CHEMBL31
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,7
- Polarare Oberfläche (TPSA)
- 82,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 27
- Formalladung
- 0
- Komplexität
- 653
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
LogP2.6
Solubility6.31e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
182-185 °C
182 - 185 °C
Physical DescriptionSolid
Dissociation Constants
8.74
6
6
9.4
Collision Cross Section
189.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
189.03 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (97.5%)
Toxikologische Informationen
Treatment
In the event of acute oral overdose, the stomach should be emptied by inducing vomiting or by gastric lavage. The patient should be carefully observed (including ECG monitoring) and given symptomatic and supportive treatment. Adequate hydration should be maintained. (L1712)
Health EffectsAntibiotic resistance
Exposure RoutesOphthalmic. Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%
Toxicity SummaryThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Signs and SymptomsThe most common side effects from antibiotics are diarrhea, nausea, vomiting. Fungal infections of the mouth, digestive tract and vagina can also occur with antibiotics
Chemie und Industrie
Pharmakologische Informationen
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QS - Sensory organs
QJ - Antiinfectives for systemic use
Protein Binding20%
Pharmacodynamics
Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.
Mechanism of ActionThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Biological Half-Life7-14 hours
Metabolism/Metabolites
Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites
Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites Half Life: 7-14 hours
FDA Pharmacological Classification
81485Y3A9A
GATIFLOXACIN ANHYDROUS
Established Pharmacologic Class [EPC] - Quinolone Antimicrobial
Chemical Structure [CS] - Quinolones
Gatifloxacin anhydrous is a Quinolone Antimicrobial.
Zugehörige Reaktionen
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