Grepafloxacin

HCID 72474

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Grundinformationen

CAS: 119914-60-2
Standard-SMILES: Cc1c(F)c(N2CCNC(C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1
InChIKey: AIJTTZAVMXIJGM-UHFFFAOYSA-N
Summenformel: C19H22FN3O3
Durchschnittliche Molmasse: 359,4 g/mol
Monoisotopische Masse: 359,16451978

Überblick

Grepafloxacin is a member of quinolines, a quinolone antibiotic and a fluoroquinolone antibiotic.

Namen und Bezeichner

Bevorzugter Name: Grepafloxacin
IUPAC: 1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
Englischer Name: Grepafloxacin
Summenformel: C19H22FN3O3
Molmasse: 359.39

Namen und Synonyme

Grepafloxacin119914-60-21-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidGrepafloxacineGrepafloxacino1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidL1M1U2HC313-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-OPC-17116DTXSID2048321grepafloxacinumRefChem:922501

Weitere Namen anzeigen

dl-GrepafloxacinGrepafloxacin USP/EP/BPGrepafloxacin/OPC-17116/dl-Grepafloxacin1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

DTXCID0028296J01MA11(+--)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid(RS)-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid631-454-3Raxar146863-02-7dl-Grepafloxacin Hydrochloride

Datenbank-Bezeichner

CAS: 119914-60-2
PubChem CID: 72474
DTXSID: DTXSID2048321
ChEMBL: CHEMBL583
ChEBI: CHEBI:5543
UNII: L1M1U2HC31
EC Number: 631-454-3
Nikkaji: J384.494C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,2
Polarare Oberfläche (TPSA): 72,9 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 7
Frei drehbare Bindungen: 3
Schwere Atome: 26
Formalladung: 0
Komplexität: 636

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Antibiotics

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

LogP2.9

Solubility6.32e-01 g/L

Human DrugsPharmaceuticals

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt: 189 · 189-192 ºC
Siedepunkt: 610 · 610.0±55.0 °C(Predicted)
Dichte: 1.366 · 1.366
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit: DMSO (Slightly), Methanol (Slightly)
Aggregatzustand: Solid
pka: 6.44 · 6.44±0.50(Predicted)
Farbe: Pale Beige to Pale Yellow
Stabilität: Hygroscopic
CAS Datenbank: 119914 · 119914-60-2(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Sicherheitsdaten

Alarmwort: Achtung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H301

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding50%

PharmacodynamicsGrepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.

Mechanism of ActionGrepafloxacin exerts its antibacterial activity by inhibiting bacterial topoisomerase II (DNA gyrase) and topoisomerase IV, essential enzymes for duplication, transcription, and repair of bacterial DNA.

Biological Half-Life15 ± 3 hours

Metabolism/Metabolites · 1 Eintrag

Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity