Cefoperazon
CEFOPERAZONE ACID · Cefoperazone (Cefobid) · (6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid · 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-(4-hydroxyphenyl)acetyl]aMino]-3-[[(1-Methyl-1H-tetrazol-5-yl)thio]Methyl]-8-oxo-,(6R,7R)- · Cefob · l~rdum · Medocef · CEFOPERAZONE
Identifikatoren & physikalische Daten
| CAS No. | 62893-19-0 |
|---|---|
| Summenformel | C25H27N9O8S2 |
| Durchschnittliche Molmasse | 645,7 g/mol |
| Monoisotopische Masse | 645,1424012 g/mol |
| SMILES | CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(CSc4nnnn4C)CS[C@H]23)c2ccc(O)cc2)C(=O)C1=O |
| InChIKey | GCFBRXLSHGKWDP-XCGNWRKASA-N |
| PubChem CID | 44187 |
| ChEMBL | CHEMBL507674 |
| ChEBI | CHEBI:3493 |
| EC No. | 263-749-4 |
| DTXSID | DTXSID2022759 |
| Lokaler Name | Cefoperazon |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 271 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 13 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 44 |
| Formalladung | 0 |
| Komplexität | 1.250 |
| Arzneimittel | Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | -0.74 |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsCephalosporinsPharmaceuticals |
| Animal Drugs | Pharmaceuticals -> UK Veterinary Medicines Directorate List |
| Schmelzpunkt | 188-190169-171 C |
| Collision Cross Section | 239.1 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]238.72 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Dichte | 1.77±0.1 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 2.6 (Uncertain) |
| Farbe | White to Off-White |
| Merck | 14,1930 |
| InChIKey | GCFBRXLSHGKWDP-XCGNWRKASA-N |
| SMILES | N12[C@@]([H])([C@H](NC([C@H](NC(N3CCN(CC)C(=O)C3=O)=O)C3=CC=C(O)C=C3)=O)C1=O)SCC(CSC1N(C)N=NN=1)=C2C(O)=O |
| CAS Datenbank | 62893-19-0(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | REACH registered substance: Cefoperazone (EC: 263-749-4) |
| Weitere Sicherheitsinformationen | IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Environment tier I assessment |
| Hazard Classes and Categories | Skin Sens. 1 (100%) |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)cefoperazoneDILI PositiveIntravenousDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Zollcode | 29419000 |
| RTECS-Nr. | XI0373900 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36 |
Anwendungen & Verwendung
Beschreibung
Cefoperazone has a C-7 side chain reminiscent of piperacillin's and also possesses the C-3 side chain (MTT ) that often is associated with the bleeding and alcohol intolerance problems among patients taking cephalosporins. Its useful activity against pseudomonads partly compensates for this, although it is not potent enough to be used as a single agent against this difficult pathogen. The C-7 side chain does not convey sufficient resistance to many β-lactamases, although the addition of clavulanic acid or sulbactam would presumably help.
Verwenden
Cefoperazone also has a broad spectrum of antimicrobial action, including most clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is stable with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria. Cefoperazone is used for bacterial infections of the lower respiratory tract, urinary and sexual tracts, bones, joints, skin, soft tissues, abdominal, and gynecological infections. Synonyms of this drug are cefazon, cefobid, cefobis, and many others.