7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-1-ium-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylate
Grundinformationen
- CAS
151096-09-2- Standard-SMILES
COc1c(N2C[C@@H]3CCC[NH2+][C@@H]3C2)c(F)cc2c(=O)c(C(=O)[O-])cn(C3CC3)c12- InChIKey
FABPRXSRWADJSP-MEDUHNTESA-N- Summenformel
- C21H24FN3O4
- Durchschnittliche Molmasse
- 401,4 g/mol
- Monoisotopische Masse
- 401,17508442
Überblick
Moxifloxacin is a synthetic fluoroquinolone antibiotic agent. Bayer AG developed the drug (initially called BAY 12-8039) and it is marketed worldwide (as the hydrochloride) under the brand name Avelox (in some countries also Avalox) for oral treatment.
Namen und Bezeichner
- Bevorzugter Name
- 7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-1-ium-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylate
- IUPAC
- 7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-1-ium-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylate
- Englischer Name
- Moxifloxacin
- Summenformel
- C21H24FN3O4
- Molmasse
- 401.43
Namen und Synonyme
1-Cyclopropyl-6-fluoro-8-methoxy-7-(octahydro-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acidCS-83AvdoxAids070017Aids-070017MOXIFLOXACINMAXIOFFOXACINMoxifloxacin(Hclform)Moxifloxacin USP/EP/BP
Datenbank-Bezeichner
- CAS
151096-09-2、354812-41-2- PubChem CID
- 40467042
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 89,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 721
Experimentelle und physikochemische Eigenschaften
LogP2.9
Solubility1.68e-01 g/L
Melting Point
238-242 °C
238 - 242 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 203 · 203-208 C
- Siedepunkt
- 636.4 · 636.4±55.0 °C(Predicted)
- Dichte
- 1.408 · 1.408±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C(protect from light)
- Löslichkeit
- Acetonitrile (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly)
- pka
- 6.43 · 6.43±0.50(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Off-White to Light Yellow
- Stabilität
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 2
- risk_code
- 22-40
- hazard_code
- Xn
- safety_code
- 36/37
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 151096-09-2(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
Protein Binding50% bound to serum proteins, independent of drug concentration.
Pharmacodynamics
Moxifloxacin is a quinolone/fluoroquinolone antibiotic. Moxifloxacin can be used to treat infections caused by the following bacteria: Aerobic Gram-positive microorganisms: _Corynebacterium_ species, _Micrococcus luteus_, _Staphylococcus aureus_, _Staphylococcus epidermidis_, _Staphylococcus haemolyticus_, _Staphylococcus hominis_, _Staphylococcus warneri_, _Streptococcus pneumoniae_, and _Streptococcus viridans_ group. Aerobic Gram-negative microorganisms: _Acinetobacter lwoffii_, _Haemophilus influenzae_, and _Haemophilus parainfluenzae_. Other microorganisms: _Chlamydia trachomatis_. Moxifloxacin 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. Moxifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.
Mechanism of Action
The bactericidal action of moxifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during bacterial cell division.
Biological Half-Life11.5-15.6 hours (single dose, oral)
Metabolism/Metabolites
Approximately 52% or oral or intravenous dose is metabolized via glucuronide and sulphate conjugation. The cytochrome P450 system is not involved in metabolism. The sulphate conjugate accounts for 38% of the dose, and the glucuronide conjugate accounts for 14% of the dose.
Absorption, Distribution and Excretion
Well absorbed from the gastrointestinal tract. Absolute oral bioavailability is approximately 90%. Food has little effect on absorption.
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