4-Butyl-1,2-diphenyl-3,5-pyrazoli-dindion
PBZ · phenylbutazon · 4-Phenylbutazone · Benzone · Baotaisong · Butadione · Pyrazolidin · 4-BUTYL-1,2-DIPHENYL-3,5-PYRAZOLIDINEDIONE
Identifikatoren & physikalische Daten
| CAS No. | 50-33-9 |
|---|---|
| Summenformel | C19H20N2O2 |
| Durchschnittliche Molmasse | 308,4 g/mol |
| Monoisotopische Masse | 308,15247789 g/mol |
| SMILES | CCCCC1C(=O)N(c2ccccc2)N(c2ccccc2)C1=O |
| InChIKey | VYMDGNCVAMGZFE-UHFFFAOYSA-N |
| PubChem CID | 4781 |
| ChEMBL | CHEMBL101 |
| ChEBI | CHEBI:48574 |
| EC No. | 200-029-0 |
| DTXSID | DTXSID9021136 |
| Lokaler Name | 4-Butyl-1,2-diphenyl-3,5-pyrazoli-dindion |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 389 |
| pH | pH of aqueous solution = 8.2 |
| LogP (Verteilungskoeffizient) | 3.16log Kow = 3.163.7 |
| LogS | -3.81 |
| Geruch | ODORLESSVery slight aromatic odor |
| Geschmack | Slightly bitter taste |
| Color/Form | Crystals from ethanolWhite or very-light-yellow powder |
| Löslichkeit | less than 1 mg/mL at 74.3 °F (NTP, 1992)47.5Freely soluble in acetone, ether, and ethyl acetate1 G IN ABOUT 20 ML ALCOHOLSolubility in water at 22.5 °C: 0.7 mg/mL (also 2.2 mg/mL)In water, 34 mg/L at 25 °CPractically insoluble in water, sparingly soluble in alcohol. It dissolves in alkaline solutions.<0.1 g/100 mL at 23.5 ºC |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 219 to 225 °F (NTP, 1992)105105 °CMP: 140-141 °C (solidifies and remelts at approximately 180 °C) /Phenylbutazone piperazine salt/106-108 °C (lit.) |
| Brechungsindex | INDICES OF REFRACTION: 1.600 (ALPHA), 1.620 (GAMMA)1.6140 (estimate) |
| Physical Description | Phenylbutazone appears as odorless white or off-white crystalline powder. Tasteless at first, but slightly bitter aftertaste. pH (aqueous solution) 8.2. (NTP, 1992)Solid |
| Dissociation Constants | 4.5 |
| Siedepunkt | 448.76°C (rough estimate) |
| Dichte | 1.1591 (rough estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 4.5(at 25℃) |
| Farbe | White to almost white |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,7277 |
| BRN | 290080 |
| Henry-Konstante | 1.5×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong acids, strong bases. |
| Hauptanwendungen | forensics and toxicologyveterinary |
| InChI | 1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3 |
| InChIKey | VYMDGNCVAMGZFE-UHFFFAOYSA-N |
| SMILES | CCCCC1C(=O)N(N(C1=O)c2ccccc2)c3ccccc3 |
| LogP (Verteilungskoeffizient) | 3.160 |
| CAS Datenbank | 50-33-9(CAS DataBase Reference) |
| NIST chemische Informationen | Phenylbutazone(50-33-9) |
| EPA chemische Informationen | Phenylbutazone (50-33-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (94.3%): Toxic if swallowed [Danger Acute toxicity, oral]H312 (67.1%): Harmful in contact with skin [Warning Acute toxicity, dermal]H315 (72.1%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (40%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (97.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (68.6%): Harmful if inhaled [Warning Acute toxicity, inhalation]H334 (39.3%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]H335 (72.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H351 (64.3%): Suspected of causing cancer [Warning Carcinogenicity]H361 (22.9%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, 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 140 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Phenylbutazone: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 3,5-Pyrazolidinedione, 4-butyl-1,2-diphenyl-: Human health tier I assessmentIMAP assessments - 3,5-Pyrazolidinedione, 4-butyl-1,2-diphenyl-: Environment tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available |
Anwendungen & Verwendung
Beschreibung
Phenylbutazone, one of the earliest NSAIDs introduced, is now indicated for the symptomatic relief of rheumatoid arthritis, osteoarthritis, psoriatic arthritis, ankylosing spondylitis, gout, and acute superficial thrombophlebitis. The gastrointestinal and bone marrow toxicity observed in its early use have been greatly reduced by lower dosage (300 mg/d). Nevertheless, it is used primarily where other drugs have failed and then only for short-term therapy. The drug has a long serum half-life of about 100 h. It is a moderately active cyclooxygenase inhibitor and it suppresses both spontaneous and chemotactic motility of neutrophils. In addition to the serious gastrointestinal and hematological adverse effects, sodium and water retention, rash, vertigo, and dermatitis are observed.
Verwenden
Phenylbutazone, a nonsteroidal anti-inflammatory drug, is an efficient reducing cofactor for the peroxidase activity of COX. Phenylbutazone-dependent inactivation of COX and prostacyclin synthase is markedly increased in the presence of 100 μM hydrogen peroxide with half-maximal effects at Phenylbutazone concentrations of 100 and 25 μM for COX and prostacyclin synthase, respectively.