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Sulfadiazin
SULPHADIAZINE · SULFADIAZIN · Sulfadiazine,(S) · Sulfadiazene · Diazin · Sulfose · Terfonyl · Diazolone
Identifikatoren & physikalische Daten
| CAS No. | 68-35-9 |
|---|---|
| Summenformel | C10H10N4O2S |
| Durchschnittliche Molmasse | 250,28 g/mol |
| Monoisotopische Masse | 250,05244656 g/mol |
| SMILES | Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1 |
| InChIKey | SEEPANYCNGTZFQ-UHFFFAOYSA-N |
| PubChem CID | 5215 |
| ChEMBL | CHEMBL439 |
| ChEBI | CHEBI:9328 |
| EC No. | 200-685-8 |
| DTXSID | DTXSID7044130 |
| Lokaler Name | Sulfadiazin |
Chemische & physikalische Eigenschaften
| XLogP | -0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 106 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 327 |
| Arzneimittel | Pharmaceuticals -> Antibiotics (Sulfonamide)Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Fusion temperature |
| LogP (Verteilungskoeffizient) | -0.2-0.04 |
| Löslichkeit | 6.01e-01 g/LSoluble in dimethyl sulfoxide.67.13mg/L(25 ºC) |
| Human Drugs | FDA approved drugs -> Active ingredientAnti-infective medicines |
| Animal Drugs | Active Ingredients (Sulfadiazine) -> FDA GreenbookPharmaceuticals -> UK Veterinary Medicines Directorate ListPharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Physical Description | Solid |
| Dissociation Constants | 6.36 |
| Collision Cross Section | 153.9 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]150.9 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]148.7 Ų [M+H]+ [CCS Type: TW]157.85 Ų [M+Na]+ [CCS Type: TW151.96 Ų [M+H]+ |
| Schmelzpunkt | 253 °C (dec.) (lit.) |
| Siedepunkt | 512.6±52.0 °C(Predicted) |
| Dichte | 1.3780 (rough estimate) |
| Brechungsindex | 1.6440 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain) |
| Aggregatzustand | powder |
| Farbe | white |
| Merck | 14,8903 |
| BRN | 6733588 |
| BCS Class | 4/3 |
| Hauptanwendungen | clinical testing |
| InChI | 1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14) |
| InChIKey | SEEPANYCNGTZFQ-UHFFFAOYSA-N |
| SMILES | Nc1ccc(cc1)S(=O)(=O)Nc2ncccn2 |
| CAS Datenbank | 68-35-9(CAS DataBase Reference) |
| NIST chemische Informationen | Sulfadiazine(68-35-9) |
| EPA chemische Informationen | Benzenesulfonamide, 4-amino-N-2-pyrimidinyl- (68-35-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.2% (2 of 171) of reports.DangerH302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P233, P260, P261, P263, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 171 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 23-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17511Sulphadiazine: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (98.2%) |
| Hepatotoxicity | Sulfadiazine, like other sulfonamides, causes a characteristic idiosyncratic liver injury which has features of drug-allergy or hypersensitivity. The typical onset is sudden development of fever and rash followed by jaundice within a few days or weeks of starting the medication. The pattern of injury is typically mixed, although fatal cases are often hepatocellular and prolonged cholestatic cases have also been described. Eosinophilia or atypical lymphocytosis are also common and the clinical pattern can be considered a part of DRESS syndrome (drug rash with eosinophilia and systemic symptoms). Cases of Stevens Johnson syndrome due to sulfadiazine have also been described. Sulfonamides such as sulfadiazine have been linked to many cases of acute liver failure and as a class, the sulfonamides still rank in the top 5 to 10 causes of drug induced, idiosyncratic fulminant hepatic failure. However, most cases of sulfonamide induced liver injury resolve rapidly, usually within 2 to 4 weeks unless cholestasis is severe. Onset of injury is more rapid with rechallenge and can appear within a day or reexposure. Patients with hepatic injury due to sulfadiazine may have a history of previous exposure to the drug without injury. Sulfonamides such as sulfadiazine can also cause mild and transient ALT elevations that do not progress to jaundice or more severe liver injury either alone or as a part of a generalized hypersensitivity reaction. Sulfonamides have also been linked to hepatic granulomas. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)SulfadiazinevLess-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| F | 10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3249 |
| Zollcode | 29335990 |
| RTECS-Nr. | WP1925000 |
| R-Sätze (R) | 22-36/37/38-42/43-43-42 |
| Toxizität | LD50 oral in mouse: 1500mg/kg |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralAquatic Chronic 2Repr. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
It is used in the form of silver salts (sulfadiazine silver) as an external antibacterial agent, primarily for treating burns. It is believed that the presence of the silver ion in the molecule facilitates increased antimicrobial and wound-healing action.