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(±)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure
2-(2-Fluoro-[1,1'-biphenyl]-4-yl)propanoic acid · ANSAID · Zepolas · rac-Flurbiprofen · 2-(2-fluorobiphenyl-4-yl)propanoic acid · fp70 · ANSIDE · Adfeed
![Molekülstruktur von (±)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure](/img/chemical/3394.png)
Identifikatoren & physikalische Daten
| CAS No. | 5104-49-4 |
|---|---|
| Summenformel | C15H13FO2 |
| Durchschnittliche Molmasse | 244,26 g/mol |
| Monoisotopische Masse | 244,08995788 g/mol |
| SMILES | CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1 |
| InChIKey | SYTBZMRGLBWNTM-UHFFFAOYSA-N |
| PubChem CID | 3394 |
| ChEMBL | CHEMBL563 |
| ChEBI | CHEBI:5130 |
| EC No. | 225-827-6 |
| DTXSID | DTXSID0037231 |
| Lokaler Name | Flurbiprofen |
Chemische & physikalische Eigenschaften
| XLogP | 4,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 286 |
| Arzneimittel | Pharmaceuticals -> Musculo-skeletal system -> Anti-inflammatory and antirheumatic productsPharmaceuticals -> Analgesics and anti-inflammatories |
| LogP (Verteilungskoeffizient) | 3.8 |
| Löslichkeit | 2.49e-02 g/Lmethanol: soluble50mg/mL8mg/L(room temperature) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, NonsteroidalFDA approved drugs -> Active ingredientPharmaceuticals |
| Schmelzpunkt | 110-111 °C110 - 111 °C110-112 °C(lit.) |
| Physical Description | Solid |
| Dissociation Constants | 4.034.224.3 |
| Collision Cross Section | 155.9 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 376.2±30.0 °C(Predicted) |
| Dichte | 1.1795 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | pKa 3.80(H2O) (Uncertain) |
| Aggregatzustand | White solid |
| Farbe | white to off-white |
| Biologische Quelle | synthetic |
| Merck | 14,4199 |
| InChI | InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18) |
| InChIKey | SYTBZMRGLBWNTM-UHFFFAOYSA-N |
| SMILES | FC1C=C(C=CC=1C1C=CC=CC=1)C(C)C(=O)O |
| CAS Datenbank | 5104-49-4(CAS DataBase Reference) |
| EPA chemische Informationen | [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-?-methyl- (5104-49-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (98.2%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, 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 114 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Developmental ToxicityReproductive Toxicity |
| Weitere Sicherheitsinformationen | IMAP assessments - [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-.alpha.-methyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 3 (98.2%) |
| Treatment | Patients should be managed by symptomatic and supportive care following overdose with a nonsteroidal anti-inflammatory drug. There are no specific antidotes. Emesis and/or activated charcoal (60 to 100 g in adults, 1 to 2 g/kg in children) and/or osmotic cathartic may be indicated in patients seen within 4 hours of ingestion with symptoms, or following a large overdose (5 to 10 times the usual dose). Forced diuresis, alkalization of urine, hemodialysis, or hemoperfusion may not be useful due to high protein binding. (L1712) |
| Hepatotoxicity | Prospective studies show that mild elevations in serum aminotransferase levels can occur in up to 15% of patients taking NSAIDs such as flurbiprofen, but the abnormalities are generally transient, mild and asymptomatic, often resolving even with drug continuation. Marked aminotransferase elevations above 3 times the upper limit of normal (ULN) occur in less than 1% of patients. Clinically apparent liver injury with jaundice from flurbiprofen is rare and only individual case descriptions have been published. The latency to onset is within 1 to 4 weeks of starting. The pattern of enzyme elevations is typically cholestatic, but hepatocellular cases have been described. Immunoallergic features are present in some cases (low grade fever, rash), but are generally not prominent, and autoantibody formation is rare. Most cases resolve promptly on stopping therapy. Flurbiprofen is not mentioned in large case series on drug induced liver injury or acute liver failure from the United States, but was listed as the second most common agent implicated in drug-induced liver injury in a case series from Turkey, one of which was fatal. |
| Expositionspfade | Fluribiprofen is rapidly and almost completely absorbed following oral administration. Peak plasma concentrations are reached 0.5 - 4 hours after oral administration. |
| Toxizitätsübersicht | Similar to other NSAIAs, the anti-inflammatory effect of flurbiprofen occurs via reversible inhibition of cyclooxygenase (COX), the enzyme responsible for the conversion of arachidonic acid to prostaglandin G2 (PGG2) and PGG2 to prostaglandin H2 (PGH2) in the prostaglandin synthesis pathway. This effectively decreases the concentration of prostaglandins involved in inflammation, pain, swelling and fever. Flurbiprofen is a non-selective COX inhibitor and inhibits the activity of both COX-1 and -2. It is also one of the most potent NSAIAs in terms of prostaglandin inhibitory activity. |
| Signs and Symptoms | Symptoms of a flurbiprofen overdose may include nausea, vomiting, stomach pain, dizziness, drowsiness, black or bloody stools, coughing up blood, urinating less than usual or not at all, shallow breathing, fainting, or coma. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)flurbiprofenOcufen®NSAIDs3less-DILI-concern drugs |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Toxicity Data | LD50: 10 mg/kg (Oral, Dog) (A308) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1/PG 2 |
| Zollcode | 29163990 |
| RTECS-Nr. | DU8341000 |
| R-Sätze (R) | 25-23/24/25 |
| Gefahrensymbole | T,C |
| Sicherheitshinweise (S) | 36/37/39-45 |
| Gefahrenklasse | 6.1(b)Acute Tox. 3 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Flurbiprofen synthesis was originally reported in 1974. During a study of the pharmacological properties of a large number of substituted phenylalkanoic acids, including ibuprofen and ibufenac, the most potent were found to be substituted 2-(4-biphenyl)propionic acids. Further toxicological and pharmacological studies indicated that flurbiprofen possessed the most favorable therapeutic profile, so it was selected for further clinical development. It was not marketed until 1987, when it was introduced as the sodium salt as Ocufen, the first topical NSAID indicated for ophthalmic use in the United States. The indication for Ocufen is the same as that for Profenal—that is, to inhibit intraoperative miosis induced by prostaglandins in cataract surgery.
Verwenden
An anti-inflammatory used as an analgesic.