Ceftizoxime
Grundinformationen
- CAS
68401-81-0- Standard-SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=CCS[C@H]12)c1csc(N)n1- InChIKey
NNULBSISHYWZJU-LLKWHZGFSA-N- Summenformel
- C13H13N5O5S2
- Durchschnittliche Molmasse
- 383,4 g/mol
- Monoisotopische Masse
- 383,03581052
Überblick
Ceftizoxime is a parenteral third-generation cephalosporin, bearing a 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino group at the 7beta-position. It has a role as an antibacterial drug. It is a conjugate acid of a ceftizoxime(1-).
Namen und Bezeichner
- Bevorzugter Name
- Ceftizoxime
- IUPAC
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Englischer Name
- Ceftizoxime
- Summenformel
- C13H13N5O5S2
- Molmasse
- 383.4
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
68401-81-0- PubChem CID
- 6533629
- DTXSID
DTXSID5022772- ChEMBL
CHEMBL528- ChEBI
CHEBI:553473- UNII
- C43C467DPE
- EC Number
- 685-309-4
- Nikkaji
- J37.178E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0
- Polarare Oberfläche (TPSA)
- 201 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 25
- Formalladung
- 0
- Komplexität
- 669
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 227 ° · 227° (dec)
- Dichte
- 1.89 · 1.89±0.1 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- Löslichkeit
- Aqueous Base (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
- Aggregatzustand
- Solid
- pka
- 2.1 · pKa 2.1 (Uncertain)
- Farbe
- White to Pale Yellow
- Merck
- 14 · 14,1951
- Stabilität
- Hygroscopic
- InChIKey
- NNULBSISHYWZJU-LLKWHZGFSA-N
- SMILES
- N12[C@@]([H])([C@H](NC(/C(/C3=CSC(N)=N3)=N\OC)=O)C1=O)SCC=C2C(O)=O
- CAS Datenbank
- 68401 · 68401-81-0(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
ceftizoxime
DILI Negative
Intravenous
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- hs_code
- 2941906000
- RTECS-Nr.
- XI0367375
- Toxizität
- LD50 intravenous in rat: 8gm/kg
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Pharmacodynamics
Ceftizoxime is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders.
Mechanism of Action
Ceftizoxime is an aminothiazolyl cephalosporin with an extended spectrum of activity against many gram-negative, nosocomially acquired pathogens. It has excellent beta-lactamase stability, with good in vitro activity against Haemophilus influenzae, Neisseria gonorrhoeae and Klebsiella pneumoniae. Ceftizoxime, like the penicillins, is a beta-lactam antibiotic. 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; it is possible that ceftizoxime interferes with an autolysin inhibitor.
FDA Pharmacological Classification
C43C467DPE
CEFTIZOXIME
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Ceftizoxime is a Cephalosporin Antibacterial.
Absorption, Distribution and Excretion
Excreted virtually unchanged by the kidneys in 24 hours.
The mean apparent volume of distribution ranges between 15 - 28L.
Anwendungen
BeschreibungIn ceftizoxime, the whole C-3 side chain has been omitted to prevent deactivation by hydrolysis. It rather resembles cefotaxime in its properties; however, not being subject to metabolism, its pharmacokinetic properties are much less complex.
VerwendenCeftizoxime is used for bacterial infections of the lower respiratory tract, infections of the urinary tract, infections of the bones, joints, skin, soft tissues, and abdominal infections. Synonyms of this drug are ceftix and eposerin.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter100 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A parenteral third-generation cephalosporin, bearing a 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino group at the 7beta-position.
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