1,2-Diphenyl-4-(2-(phenylsulfi-nyl)ethyl)-3,5-pyrazolidindion
SULFINPYRAZONE · g28315 · anturan · anturen · enturan · enturen · g28,315 · anturane
Identifikatoren & physikalische Daten
| CAS No. | 57-96-5 |
|---|---|
| Summenformel | C23H20N2O3S |
| Durchschnittliche Molmasse | 404,5 g/mol |
| Monoisotopische Masse | 404,1194635 g/mol |
| SMILES | O=C1C(CCS(=O)c2ccccc2)C(=O)N(c2ccccc2)N1c1ccccc1 |
| InChIKey | MBGGBVCUIVRRBF-UHFFFAOYSA-N |
| PubChem CID | 5342 |
| ChEMBL | CHEMBL832 |
| ChEBI | CHEBI:9342 |
| EC No. | 200-357-4 |
| DTXSID | DTXSID0023618 |
| Lokaler Name | 1,2-Diphenyl-4-(2-(phenylsulfi-nyl)ethyl)-3,5-pyrazolidindion |
Chemische & physikalische Eigenschaften
| XLogP | 2,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 76,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 29 |
| Formalladung | 0 |
| Komplexität | 571 |
| LogP (Verteilungskoeffizient) | 2.4 |
| Color/Form | WHITE TO OFF-WHITE |
| Löslichkeit | SOL IN ETHYL ACETATE, CHLOROFORMSLIGHTLY SOL IN WATER, ALC, ETHER, MINERAL OILSSLIGHTLY SOL IN FATS1 G SOL IN 10 ML ACETONE & 10 ML 0.5 N NAOHFor more Solubility (Complete) data for SULFINPYRAZONE (6 total), please visit the HSDB record page.Very slightly soluble in water, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.2.601g/L(22 ºC) |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Schmelzpunkt | 136-137 °CMELTING POINT: 130-133 °C /D-FORM, L-FORM/136 - 137 °C136-137° |
| Physical Description | Solid |
| Stability/Shelf Life | STABLE TO LIGHT & AIR |
| Dissociation Constants | 3.25PKA: 2.8 |
| Collision Cross Section | 193.5 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]199.9 Ų [M+K]+ [CCS Type: TW |
| Other Experimental Properties | CRYSTALS FROM CHLOROFORM & HEPTANECRYSTALS FROM ETHANOL /D-FORM/CRYSTALS /L-FORM/SPECIFIC OPTICAL ROTATION: +67.1 DEG @ 22 °C/D (C= 2.04 IN ETHANOL)+109.3 DEG @ 25 °C/D (C= 0.5 IN CHLOROFORM) /D-/SPECIFIC OPTICAL ROTATION: -64.2 DEG @ 23 °C/D (C= 2.14 IN ETHANOL)-104.5 DEG @ 26 °C/D (C= 0.5 IN CHLOROFORM) /L-/ |
| Siedepunkt | 590.8±42.0 °C(Predicted) |
| Dichte | 1.1890 (rough estimate) |
| Brechungsindex | 1.6360 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 2.8(H2O t = RT I undefined) (Uncertain) |
| Farbe | Off-White to Light Brown |
| Hauptanwendungen | cleaning productscosmeticsfood and beveragesforensics and toxicologypersonal carepharmaceutical (small molecule)veterinary |
| InChI | 1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2 |
| InChIKey | MBGGBVCUIVRRBF-UHFFFAOYSA-N |
| SMILES | O=C1C(CCS(=O)c2ccccc2)C(=O)N(N1c3ccccc3)c4ccccc4 |
| CAS Datenbank | 57-96-5(CAS DataBase Reference) |
| NIST chemische Informationen | Sulfinpyrazone(57-96-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 70 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - 3,5-Pyrazolidinedione, 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]-: Human health tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wechselwirkungen | ...URICOSURIC ACTION /OF SULFINPYRAZONE/ IS ADDITIVE TO THAT OF PROBENECID & PHENYLBUTAZONE BUT IS MUTUALLY ANTAGONISTIC TO THAT OF SALICYLATES. ... POSSESSES ABILITY TO DISPLACE OTHER ORG ANIONS THAT ARE BOUND EXTENSIVELY TO PLASMA PROTEINS...THUS ALTERING THEIR DISTRIBUTION TO TISSUES & THEIR RENAL EXCRETION......SULFINPYRAZONE MAY POTENTIATE ACTIONS OF INSULIN & ORAL HYPOGLYCEMIC AGENTS...SULFINPYRAZONE MAY DISPLACE SULFONAMIDES FROM PLASMA PROTEIN BINDING SITES... |
| Human Toxicity Excerpts | HYPERSENSITIVITY REACTIONS, USUALLY A RASH WITH FEVER, DO OCCUR.../OCCASIONALLY/SIDE EFFECTS INCL UPPER GI DISTURBANCES...&, RARELY, ANEMIA, LEUKOPENIA, AGRANULOCYTOSIS, & THROMBOCYTOPENIA. |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 2933194350 |
| RTECS-Nr. | UQ8575000 |
| R-Sätze (R) | 22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 57-96-5(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Beschreibung
Sulfinpyrazone is soluble in alkaline solutions. Its synthesis is similar to that of phenylbutazone (Fig. 36.33). It produces its uricosuric effect in a manner similar to that of probenecid. A dose of 35 mg produces a uricosuric effect equivalent to that produced by 100 mg of probenecid, whereas 400 mg/day of sulfinpyrazone produces an effect comparable to that obtained with doses of 1.5 to 2 g of probenecid. It also possesses, not surprisingly, some of the properties of phenylbutazone. It is an inhibitor of human platelet prostaglandin synthesis at the cyclooxygenase step, resulting in a decrease in platelet release and a reduction in platelet aggregation. This antiplatelet effect suggests a role for sulfinpyrazone in reducing the incidence of sudden death, which can occur in the first year following a myocardial infarction; however, it lacks the analgetic and anti-inflammatory effects of phenylbutazone.
Verwenden
As an anti-inflammatory and uricosuric agent, its side effects were severe enough to preclude its continuous use in the treatment of chronic gout. Evaluation of several chemical congeners indicated that the phenylthioethyl analog of phenylbutazone had promising anti-inflammatory and uricosuric activity. A metabolite, the sulfoxide pyrazone, exhibited enhanced uricosuric activity. Interestingly, the corresponding sulfone does not appear to be a metabolite. Sulfinpyrazone lacks the clinically striking anti-inflammatory and analgesic properties of phenylbutazone.