Grundinformationen
- Standard-SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1- InChIKey
JFPVXVDWJQMJEE-IZRZKJBUSA-N- Summenformel
- C16H16N4O8S
- Durchschnittliche Molmasse
- 424,4 g/mol
- Monoisotopische Masse
- 424,06888447
Überblick
Cefuroxime is a 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain. It has a role as a drug allergen. It is a member of furans, a 3-(carbamoyloxymethyl)cephalosporin and an oxime O-ether.
Namen und Bezeichner
- Bevorzugter Name
- Cefuroxime
- IUPAC
- (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Englischer Name
- Cefuroxime
- Summenformel
- C16H16N4O8S
- Molmasse
- 424.39
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
55268-75-2- PubChem CID
- 5479529
- DTXSID
DTXSID5022774- ChEMBL
CHEMBL1436- ChEBI
CHEBI:3515- UNII
- O1R9FJ93ED
- EC Number
- 259-560-1
- Nikkaji
- J13.093A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,2
- Polarare Oberfläche (TPSA)
- 199 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 798
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Metabolite of Cefuroxime axetil
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Antibiotics
LogP
-0.8
-0.17
Solubility
Freely soluble as sodium salt (145 mg/L)
2.84e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
Watch group antibiotics
Melting Point
218-225 °C
218 - 225 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 171.5 · 171.5-173°C
- Dichte
- 1.76 · 1.76
- Brechungsindex
- 1.6 · 1.6000 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- pka
- 2.5 · pKa 2.5(H2O) (Uncertain)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Wasserlöslichkeit
- 145 mg/L · 145mg/L at 25℃
- BCS Class
- 4 · 4
- Major Application
- clinical testing
- InChIKey
- JFPVXVDWJQMJEE-IZRZKJBUSA-N
- SMILES
- N12[C@@]([H])([C@H](NC(/C(/C3=CC=CO3)=N\OC)=O)C1=O)SCC(COC(N)=O)=C2C(O)=O
- CAS Datenbank
- 55268 · 55268-75-2(CAS DataBase Reference)
- EPA chemische Informationen
- 5 · 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)- (55268-75-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H317 (31%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Status: Active Update: 08-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21969
Cefuroxime: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Toxikologische Informationen
Adverse Effects
Similar to penicillins and most β-lactam antibiotics, cefuroxime is generally well-tolerated. However, cefuroxime may potentially lead to adverse drug reactions in some patients, as seen with other medications. The most commonly reported adverse drug reactions are gastrointestinal disturbances, including nausea, vomiting, and diarrhea. Additional gastrointestinal adverse drug reactions include anorexia, abdominal pain, dizziness, and headache. In cases of parenteral administration, local reactions at the injection site, including thrombophlebitis, can occur.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefuroxime
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- 3
- RTECS-Nr.
- XI0329000
- risk_code
- 42/43
- hazard_code
- Xn
- safety_code
- 22-24-37-45
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
S - Sensory organs
QJ - Antiinfectives for systemic use
QS - Sensory organs
QJ - Antiinfectives for systemic use
J01DC02
Pharmacodynamics
Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: <i>Staphylococcus aureus</i>, <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>. Aerobic Gram-negative Microorganisms: <i>Escherichia coli</i>, <i>Haemophilus influenzae</i> (including beta-lactamase-producing strains), <i>Haemophilus parainfluenzae</i>, <i>Klebsiella pneumoniae</i>, <i>Moraxella catarrhalis</i> (including beta-lactamase-producing strains), <i>Neisseria gonorrhoeae</i> (including beta-lactamase-producing strains). Spirochetes: <i>Borrelia burgdorferi</i>. Cefuroxime axetil is the prodrug
Mechanism of Action
Cefuroxime, 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 cefuroxime interferes with an autolysin inhibitor.
FDA Pharmacological Classification
O1R9FJ93ED
CEFUROXIME
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefuroxime is a Cephalosporin Antibacterial.
CEFUROXIME
Verwendung und Herstellung
Anwendungen
BeschreibungCefuroxime axetil is the acetoxyethyl ester and oral prodrug of cefuroxime, a second-generation cephalosporin. It has a broad spectrum of action and is resistant to most P-lactamases. Cefuroxime axed is indicated for serious bacterial infections, especially where no identification of organism(s) has been made.
VerwendenCefuroxime is a second-generation cephalosporin antibiotic.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.
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