Grundinformationen
- CAS
10206-21-0- Standard-SMILES
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CC#N)[C@H]2SC1- InChIKey
RRYMAQUWDLIUPV-BXKDBHETSA-N- Summenformel
- C13H13N3O6S
- Durchschnittliche Molmasse
- 339,33 g/mol
- Monoisotopische Masse
- 339,05250632
Überblick
Cefacetrile is a cephalosporin.
Namen und Bezeichner
- Bevorzugter Name
- Cefacetrile
- IUPAC
- (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Lokaler Name
- Cefacetril
- Englischer Name
- cefacetrile
- Summenformel
- C13H13N3O6S
- Molmasse
- 339.32
Namen und Synonyme
CefacetrileCephacetrile10206-21-0Vetrimast(6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCIBA 36,278A-BAFDM21QQ344C 36278 BaDTXSID0022779(6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-((acetyloxy)methyl)-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-3-(acetyloxymethyl)-7-((2-cyanoacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
Weitere Namen anzeigen
CefacetrilumCefepime APICefaloranic Acid APIcefacetrile USP/EP/BPCefcapene Pivoxil APICefacetrilum [inn-latin]Cephacetrile,Cefacetrile
RefChem:124361DTXCID302779C36278Ba5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-((cyanoacetyl)amino)-8-oxo-, monosodium salt, (6R-trans)-233-508-8CelosporCefacetrilCefacetrilo
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,5
- Polarare Oberfläche (TPSA)
- 162 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 664
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP
-0.45
-0.45
Solubility2.43e+00 g/L
Melting Point168-170
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 133 · 133-135°C
- Siedepunkt
- 757.5 · 757.5±60.0 °C(Predicted)
- Dichte
- 1.59 · 1.59±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- Löslichkeit
- DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 1.97 · pKa 1.97 (Uncertain)
- Aggregatzustand
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 3
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding23 to 38%
Pharmacodynamics
Cefacetrile is effective against many Gram-positive bacterial strains and somewhat less effective against Gram-negative species. It works by inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.
Mechanism of Action
In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.
Biological Half-Life1.2 hours
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionVd of 0.2 to 0.5L/.kg
Cellular LocationsExtracellular
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Zugehörige Reaktionen
1
Notizen zur Verbindung
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