HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cefuroxime
CEFUROXIME AXETIL · Cefuroxime acid · cefuroxim · Cephuroxime · Cefuroxime VETRANAL · Cefuroxime Axetil EP Impurity D · -8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid · CXM
Identifikatoren & physikalische Daten
| CAS No. | 55268-75-2 |
|---|---|
| Summenformel | C16H16N4O8S |
| Durchschnittliche Molmasse | 424,4 g/mol |
| Monoisotopische Masse | 424,06888447 g/mol |
| 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 |
| PubChem CID | 5479529 |
| ChEMBL | CHEMBL1436 |
| ChEBI | CHEBI:3515 |
| EC No. | 259-560-1 |
| DTXSID | DTXSID5022774 |
Chemische & physikalische Eigenschaften
| XLogP | -0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 199 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 10 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 29 |
| Formalladung | 0 |
| Komplexität | 798 |
| Arzneimittel | Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Cefuroxime axetilPharmaceuticals -> Used in Switzerland |
| LogP (Verteilungskoeffizient) | -0.8-0.17 |
| Löslichkeit | Freely soluble as sodium salt (145 mg/L)2.84e-01 g/LDMSO (Slightly), Methanol (Slightly)145mg/L at 25℃ |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsCephalosporinsFDA approved drugs -> Active ingredientWatch group antibiotics |
| Schmelzpunkt | 218-225 °C218 - 225 °C171.5-173°C |
| Physical Description | Solid |
| Dichte | 1.76 |
| Brechungsindex | 1.6000 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | pKa 2.5(H2O) (Uncertain) |
| Aggregatzustand | Solid |
| Farbe | White to Off-White |
| BCS Class | 4 |
| Hauptanwendungen | 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 | 55268-75-2(CAS DataBase Reference) |
| EPA chemische Informationen | 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 & Vorschriften
| GHS-Einstufung | DangerH317 (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. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 08-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21969Cefuroxime: 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. |
| Weitere Sicherheitsinformationen | IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6.alpha.,7.beta.(Z)]]-: Human health tier I assessment |
| Hazard Classes and Categories | Skin Sens. 1 (31%) |
| Unerwünschte Wirkungen | 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. |
| Toxizitätsübersicht | Signs and Symptoms of Overdose |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)cefuroximeDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | 3 |
| RTECS-Nr. | XI0329000 |
| R-Sätze (R) | 42/43 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-24-37-45 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Cefuroxime 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.
Verwenden
Cefuroxime is a second-generation cephalosporin antibiotic.