Fenbufen
4-([1,1'-Biphenyl]-4-yl)-4-oxobutanoic acid · bufemid · cl82204 · napanol · cinopal · Cinopol · enbufen · lederfen
Identifikatoren & physikalische Daten
| CAS No. | 36330-85-5 |
|---|---|
| Summenformel | C16H14O3 |
| Durchschnittliche Molmasse | 254,28 g/mol |
| Monoisotopische Masse | 254,09429431 g/mol |
| SMILES | O=C(O)CCC(=O)c1ccc(-c2ccccc2)cc1 |
| InChIKey | ZPAKPRAICRBAOD-UHFFFAOYSA-N |
| PubChem CID | 3335 |
| ChEMBL | CHEMBL277522 |
| ChEBI | CHEBI:31599 |
| EC No. | 252-979-0 |
| DTXSID | DTXSID9023043 |
| Lokaler Name | Fenbufen |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 54,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 310 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 2.91 |
| Human Drugs | Pharmaceuticals |
| Schmelzpunkt | 185-187184-187 °C (lit.) |
| Collision Cross Section | 150.36 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 357.5°C (rough estimate) |
| Dichte | 1.1565 (rough estimate) |
| Brechungsindex | 1.5600 (estimate) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Very slightly soluble in water, slightly soluble in acetone, in ethanol (96 per cent) and in methylene chloride.2.212mg/L(25 ºC) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 4.3(H2O tundened Iundened) (Uncertain) |
| Farbe | White to off-white |
| Merck | 13,3990 |
| Hauptanwendungen | forensics and toxicologypharmaceutical (small molecule)veterinary |
| InChI | 1S/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19) |
| InChIKey | ZPAKPRAICRBAOD-UHFFFAOYSA-N |
| SMILES | OC(=O)CCC(=O)c1ccc(cc1)-c2ccccc2 |
| EPA chemische Informationen | [1,1'-Biphenyl]-4-butanoic acid, .gamma.-oxo- (36330-85-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - [1,1'-Biphenyl]-4-butanoic acid, .gamma.-oxo-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 2918300090 |
| RTECS-Nr. | DV1761000 |
| R-Sätze (R) | 25 |
| Toxizität | LD50 in various strains of mice, rats (mg/kg): 795-1673, 200-720 orally506-811, 265-575 i.p. (Bolte) |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 28-45 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Fenbufen has been found to be an effective, well-tolerated drug for the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. Fenbufen is prepared by the Friedel-Crafts (aluminum chloride – nitrobenzene) acylation of biphenyl with succinic anhydride. The compound is metabolized in humans first to 4-hydroxy-4-biphenylbutyric acid (tmax 2.5 h) then to 4-biphenyl acetic acid (tmax 7.5 h). Both metabolites are more active than fenbufen itself and circulate for several hours (t1/2 10 h). This slow conversion of fenbufen to active metabolites having relatively long plasma half-lives allows for once a day dosing with this agent.
Verwenden
Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory