Dexibuprofen
DEXIBUPROFEN · (S)-IBUPROFEN · (S)-2-(4-Isobutylphenyl)propanoic acid · (+)-Ibuprofen · Seractil · Ramelteon-7 · d-Ibuprofen · exibuprofen
Identifikatoren & physikalische Daten
| CAS No. | 51146-56-6 |
|---|---|
| Summenformel | C13H18O2 |
| Durchschnittliche Molmasse | 206,28 g/mol |
| Monoisotopische Masse | 206,13067982 g/mol |
| SMILES | CC(C)Cc1ccc([C@H](C)C(=O)O)cc1 |
| InChIKey | HEFNNWSXXWATRW-JTQLQIEISA-N |
| PubChem CID | 39912 |
| ChEMBL | CHEMBL175 |
| ChEBI | CHEBI:43415 |
| EC No. | 610-620-9 |
| DTXSID | DTXSID9048724 |
Chemische & physikalische Eigenschaften
| XLogP | 3,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 203 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland |
| Löslichkeit | Insoluble45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL |
| Schmelzpunkt | 49-5349-53 °C(lit.) |
| Siedepunkt | 285.14°C (rough estimate) |
| Dichte | 1.0364 (rough estimate) |
| Brechungsindex | 59 ° (C=2, EtOH) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | 4.41±0.10(Predicted) |
| Farbe | white |
| BRN | 3590022 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m0/s1 |
| InChIKey | HEFNNWSXXWATRW-JTQLQIEISA-N |
| SMILES | CC(C)Cc1ccc(cc1)[C@H](C)C(O)=O |
| CAS Datenbank | 51146-56-6(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (85.7%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 7 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (85.7%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29163990 |
| R-Sätze (R) | 63-22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 45-36/37 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Dexibuprofen, the S-(+)-isomer of the widely used NSAID agent ibuprofen, was launched in Austria for the treatment of rheumatoid arthritis. While the racemic compound is commonly used clinically, the antiinflammatory activity is mediated via the S-isomer by inhibition of prostaglandin synthesis. It has also been demonstrated that the R-isomer is converted to the Santipode in vivo via a CoA thioester intermediate. Since CoA plays a pivotal role in intermediary metabolism and maintenance of the [acyl-CoA], generation of R-ibuprofen-CoA competitively inhibits many CoA-dependent reactions, which consequently produces perturbations of hepatocyte Intermediary metabolism and mitocondrial function. Pure S-ibuprofen usage, therefore, is preferred allowing a reduction in dosage level and an improved side effect profile.
Verwenden
A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer