[6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz
Ulfar · sce129 · ulfaret · pyocefal · cgp7174e · monaspor · tilmapor · pseudocef
![Molekülstruktur von [6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz](/img/chemical/656644.png)
Identifikatoren & physikalische Daten
| CAS No. | 52152-93-9 |
|---|---|
| Summenformel | C22H19N4NaO8S2 |
| Durchschnittliche Molmasse | 554,5 g/mol |
| Monoisotopische Masse | 554,05420021 g/mol |
| SMILES | NC(=O)c1cc[n+](CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)[C@@H](c4ccccc4)S(=O)(=O)[O-])[C@H]3SC2)cc1.[Na+] |
| InChIKey | REACMANCWHKJSM-DWBVFMGKSA-M |
| PubChem CID | 656644 |
| ChEMBL | CHEMBL1256939 |
| ChEBI | CHEBI:31380 |
| EC No. | 257-692-4 |
| Lokaler Name | [6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 227 |
|---|---|
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 9 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 37 |
| Formalladung | 0 |
| Komplexität | 1.040 |
| Schmelzpunkt | 175 C |
| Lagerbedingungen | Inert atmosphere,Store in freezer, under -20°C |
| Löslichkeit | H2O: 50 mg/mL, clear, light yellowSoluble in water. |
| Aggregatzustand | powder or crystals |
| Farbe | Off-White to Pale Yellow |
| Merck | 13,1958 |
| Stabilität | Hygroscopic |
| InChIKey | REACMANCWHKJSM-DWBVFMGKSA-M |
| SMILES | N12C([C@@H](NC(=O)[C@H](S([O-])(=O)=O)C3C=CC=CC=3)[C@H]1SCC(C[N+]1=CC=C(C(=O)N)C=C1)=C2C([O-])=O)=O.[Na+] |&1:2,6,17,r| |
| EPA chemische Informationen | Pyridinium, 4-(aminocarbonyl)-1-[[(6R,7R)-2-carboxy-8-oxo-7-[[(2R)-phenylsulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt, monosodium salt (52152-93-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 53 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Pyridinium, 4-(aminocarbonyl)-1-[[2-carboxy-8-oxo-7-[(phenylsulfoacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, hydroxide, inner salt, monosodium salt, [6R-[6.alpha.,7.beta.(R*)]]-PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Cefsulodine sodium: 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. |
| Hazard Classes and Categories | Skin Irrit. 2 (96.2%) |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29419059 |
| RTECS-Nr. | UU1785000 |
| R-Sätze (R) | 36/37/38-42/43-20/21/22 |
| Toxizität | LD50 in mice (mg/kg): >4000 i.p.>15000 orally (Bryskier) |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 22-26-36/37-45-36 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Cefsulodin was synthesized by Takeda Chemicals Industries in 1974 by introducing the sulfobenzyl group, the same moiety as in sulbenicillin, at the 7 position of the cephem nucleus. Its side chain at the 3 position is similar to that of cephaloridine except for the carbamoyl group. The introduction of these hydrophilic groups increases the activity against Pseudomonas aeruginosa, but it markedly decreases it against gram-positive and other gramnegative bacteria. Therefore cefsulodin is used as a specific antibiotic against infections caused by the opportunistic pathogen P. aeruginosa.
Verwenden
Cefsulodin is most commonly used in CIN agar to select for Yersinia microorganisms. The compound displays a mechanism of action like many β lactam antibiotics through inhibition of cell wall synthesis by competitively inhibiting penicillin binding protein (PBP) crosslinking of peptidoglycan resulting in inhibition of the final transpeptidation step. Through the inability for Cefsulodin sodium salt hydrate to inhibit cefsulodin-resistant mutants of Pseudomonas aeruginosa PAO4089 growth displayed that Cefsulodin sodium salt hydrate may compete with PBP3 in addition to PBP1A and PBP1B.