Cefalotin
C07761 · CEPHALOTHIN · 3-Butylidene-4 · CEFALOTHIN ACID · Cephaliotin Acid · Cephalotinic acid · -3-(Acetoxymethyl) · 5-dihydrophthalide
Identifikatoren & physikalische Daten
| CAS No. | 153-61-7 |
|---|---|
| Summenformel | C16H16N2O6S2 |
| Durchschnittliche Molmasse | 396,4 g/mol |
| Monoisotopische Masse | 396,04497858 g/mol |
| SMILES | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1 |
| InChIKey | XIURVHNZVLADCM-IUODEOHRSA-N |
| PubChem CID | 6024 |
| ChEMBL | CHEMBL617 |
| ChEBI | CHEBI:124991 |
| EC No. | 205-815-7 |
| DTXSID | DTXSID4022783 |
| Lokaler Name | Cefalotin |
Chemische & physikalische Eigenschaften
| XLogP | -0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 167 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 680 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics |
| LogP (Verteilungskoeffizient) | log Kow = -0.41 (pH 2.0)-0.2 |
| Color/Form | Solid |
| Löslichkeit | WHITE TO OFF-WHITE, CRYSTALLINE POWDERPRACTICALLY ODORLESSFREELY SOL IN WATER, SALINE TS, DEXTROSE SOLUTIONSPARINGLY SOL IN METHANOLSLIGHTLY SOL IN ALCOHOLINSOL IN MOST ORGANIC SOLVENTSDEXTROROTATORYMODERATELY HYGROSCOPICDECOMP ON HEATING /SODIUM/5.21e-02 g/LDMSO (Sparingly), Dioxane (Slightly), Methanol (Slightly)158 MG/L |
| Human Drugs | Pharmaceuticals |
| Decomposition | When heated to decomposition it emits very toxic fumes of nitroxides and sulfoxides. |
| Schmelzpunkt | 160-160.5 °C160 - 160.5 °C160-161 ºC |
| Optical Rotation | Mol wt 418.42. mp 204-205 °C. Specific optical rotation = +135 °For D sodium line (c = 1.0 in water). uv max: 236, 260 nm (epsilon 12950, 9350) /Sodium salt/Specific optical rotation = +50 °For D sodium line at 20 °C (c = 1.03 in acetonitrile) |
| Physical Description | Solid |
| Stability/Shelf Life | Solutions of cephalothin may darken, especially if stored at room temperature. A slight discoloration does not affect potency. Solutions stored under refrigeration may precipitate, but the precipitate can be redissolved by warming to room temperature with constant agitation. |
| Collision Cross Section | 185.4 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 757.2±60.0 °C(Predicted) |
| Dichte | 1.4162 (rough estimate) |
| Brechungsindex | 1.6510 (estimate) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 2.5 (Uncertain) |
| Farbe | White to Off-White |
| Merck | 14,1982 |
| CAS Datenbank | 153-61-7(CAS DataBase Reference) |
| EPA chemische Informationen | Cephalothin (153-61-7) |
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 46 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | REACH registered substance: Cefalotin (EC: 205-815-7) |
| Weitere Sicherheitsinformationen | IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R-trans)-: Environment tier I assessment |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed discontinued drug products, incl cephalothin sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Cephalothin sodium/The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Cephalothin is included on this list. |
| Hazard Classes and Categories | Skin Sens. 1 (100%) |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Wechselwirkungen | Concurrent administration with probenecid may prolong the serum half-life of cephalothin.ANIMAL STUDIES INDICATED THAT FUROSEMIDE ENHANCES NEPHROTOXICITY OF...CEPHALOTHIN......CEPHALOSPORINS...MAY BE AFFECTED BY CONCURRENT USE OF SULFINPYRAZONE. DIMINISHED TUBULAR SECRETION OF...WEAK ACIDS COULD RESULT IN HIGHER & MORE SUSTAINED SERUM LEVELS & HENCE, INTENSIFICATION OF DRUG ACTIVITY. /CEPHALOSPORINS/ |
Anwendungen & Verwendung
Beschreibung
Cephalothin is a semisynthetic, beta-lactam, first-generation cephalosporin antibiotic with bactericidal activity. Cephalothin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. PBPs participate in the terminal stages of assembling the bacterial cell wall, and in reshaping the cell wall during cell division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
Verwenden
A first generation cephalosporin antibiotic with a wide range antibacterial activity. It is effective against gram-positive and gram-negative bacteria, and has been tested in respiratory disease and neuromuscular junction studies.Cephalothin is most effective against Gram-positive cocci and is also effective against several Gram-negative organisms. First generation cephalosporins are used primarily to treat skin and soft tissue infections caused by Staphylococcus and Streptococcus species. Cephalothin is ineffective against enterococci and evidence of in vitro sensitivity should be discounted.