Flurbiprofen
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| Category | Bioactive by-products |
| Catalog number | BBF-04023 |
| CAS | 5104-49-4 |
| Molecular Weight | 244.26 |
| Molecular Formula | C15H13FO2 |
| Purity | >98% |
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Description
Flurbiprofen is a member of the phenylalkanoic acid derivative family of non-steroidal anti-inflammatory drugs (NSAIDs) used to treat the inflammation and pain of arthritis.
Specification
| Synonyms | Ansaid; Froben; Antadys |
| Storage | Store at -20°C |
| IUPAC Name | 2-(3-fluoro-4-phenylphenyl)propanoic acid |
| Canonical SMILES | CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O |
| 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) |
| InChI Key | SYTBZMRGLBWNTM-UHFFFAOYSA-N |
Properties
| Appearance | White to Off-white Solid |
| Application | Anti-Inflammatory Agents, Non-Steroidal |
| Boiling Point | 376°C |
| Melting Point | 110-116°C |
| Density | 1.279 g/cm3 |
| Solubility | Soluble in DMF (25 mg/ml), DMSO (10 mg/ml), Ethanol (25 mg/ml) |
| LogP | 4.16 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 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. |
| Toxicity | LD50: 10 mg/kg (Oral, Dog). |
Reference Reading
1.The potential use of novel chitosan-coated deformable liposomes in an ocular drug delivery system.
Chen H1, Pan H2, Li P1, Wang H3, Wang X1, Pan W1, Yuan Y4. Colloids Surf B Biointerfaces. 2016 Mar 22;143:455-462. doi: 10.1016/j.colsurfb.2016.03.061. [Epub ahead of print]
In this study, novel chitosan-coated deformable liposomes (DL-CS) were proposed as an ocular drug delivery system to prolong pre-corneal retention, and improve transcorneal penetration and absorption. Flurbiprofen-loaded deformable liposomes (FP-DL) were prepared by a modified ethanol injection method and then coated with chitosan. Both DL and DL-CS exhibited a homogeneous particle size distribution, high encapsulation efficiency and good stability. After coating with 0.1% CS, the zeta potential was shifted from negative to positive. The apparent permeability coefficient of FP-DL-0.1% CS evaluated using isolated rabbit corneas was 1.29-, 1.95- and 4.59- fold greater than that of uncoated FP-DL, conventional liposomes and FP solution (P<0.01), respectively. The in vivo pre-corneal retention time and elimination dynamics were assessed using gamma scintigraphy technology. The area under the remaining activity-time of FP-DL-0.1% CS was prolonged 2.
2.Efficacy of flurbiprofen 8.75 mg spray in patients with sore throat due to an upper respiratory tract infection: A randomised controlled trial.
de Looze F1, Russo M2, Bloch M3, Montgomery B4, Shephard A5, Smith G5, Aspley S5. Eur J Gen Pract. 2016 Mar 30:1-8. [Epub ahead of print]
Background Viral infections cause most cases of pharyngitis (sore throat); consequently, antibiotics are generally not warranted. However, a treatment targeting pain and inflammation, e.g. a topical non-steroidal anti-inflammatory spray, may be helpful for patients. Objective To evaluate the efficacy and safety of flurbiprofen 8.75 mg spray. Methods This randomised, double-blind, parallel group study was conducted at six community-based clinical research centres in Australia and two in New Zealand. Adults with sore throat due to upper respiratory tract infection (onset ≤ four days) took one dose of flurbiprofen (n = 249) or placebo spray (n = 256); after six hours, they could re-dose every three-six hours as required, for three days (max. five doses/day). The primary endpoint was the area under the change from baseline curve in throat soreness from zero-two hours (AUC0-2h). The change from baseline in other sore throat symptoms also assessed efficacy.
3.Evaluation of Mutual Drug-Drug Interaction within Geneva Cocktail for Cytochrome P450 Phenotyping using Innovative Dried Blood Sampling Method.
Bosilkovska M1, Samer C1,2, Déglon J3,4, Thomas A3, Walder B5, Desmeules J1,2, Daali Y1,2. Basic Clin Pharmacol Toxicol. 2016 Mar 24. doi: 10.1111/bcpt.12586. [Epub ahead of print]
Cytochrome P450 (CYP) activity can be assessed using a 'cocktail' phenotyping approach. Recently, we have developed a cocktail (Geneva cocktail) which combines the use of low-dose probes with a low-invasiveness dried blood spots (DBS) sampling technique and a single analytical method for the phenotyping of six major CYP isoforms. We have previously demonstrated that modulation of CYP activity after pre-treatment with CYP inhibitors/inducer could be reliably predicted using Geneva cocktail. In order to further validate this cocktail, in this study we have verified whether probe drugs contained in the latter cause mutual drug-drug interactions. In a randomized, 4-way, Latin-square cross-over study, 30 healthy volunteers received low-dose caffeine, flurbiprofen, omeprazole, dextromethorphan and midazolam (a previously validated combination with no mutual drug-drug interactions); fexofenadine alone; bupropion alone or all 7 drugs simultaneously (Geneva cocktail).
4.INTERACTION OF CAMPTOTHECIN WITH HUMAN SERUM ALBUMIN DETERMINED BY FLUORESCENCE ANISOTROPY SPECTROSCOPY.
Wybranowski T, Ziomkowska B, Cyrankiewicz M, Kruszewski S. Acta Pol Pharm. 2016 Jan-Feb;73(1):29-34.
The study can be useful for understanding the interaction of camptothecin with human serum albu- min. There are two forms of camptothecin (the carboxylate form (CPT-C) and the lactone form (CPT-L)) but only the lactone one is pharmacologically active. It was reported earlier that in the presence of HSA, the active lactone form of camptothecin changes to inactive carboxylate form and it reduces the antitumor activities of camptothecin. However, those studies were performed at physiological pH (7.4) and with non-oxidized and non-glycosylated albumin. The aim of this study was to investigate the effect of oxidative stress, glycosylation, pH changes and competitor drugs on inactivation of lactone form of camptothecin in albumin solution using measurements of fluorescence anisotropy spectroscopy. It was tried to prove that in vivo camptothecin may be present in higher amount in lactone form than previously thought. Due to a reduction of pH value, a decreased rate of hydrolysis from CPT-L to CPT-C was observed.
Spectrum
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
1H NMR Spectrum
Experimental Conditions
Solvent: CDCl3
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
