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| 100mg |
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Tarenflurbil [(R)-Flurbiprofen], the R-enantiomer of flurbiprofen, is a novel and potent activator of c-Jun N terminal kinase. Also reduce Aβ secretion, but at the same time, increases the level of intracellular Aβ. May be used for Alzheimer's disease.
| ln Vitro |
(R)-Flurbiprofen, or tartenflurbil, has the ability to dramatically lower Aβ release while simultaneously raising intracellular Aβ levels. Both 9-cis-RA and unlabeled (R)-flurbiprofen competitively block the interaction of [3H]9-cis-RA with RXRα. (9-cis-retinoid acid, or 9-cis-RA) inhibits Tarenflurbil ((R)-Flurbiprofen)'s lowering of Aβ secretion, and (R)-Flurbiprofen can interfere with the interaction between RXRα and 9-cis-RA). The intracellular Aβ species levels are markedly increased upon treatment with tartenflurbil ((R)-Flurbiprofen)[1]. It is evident that second generation GSMs and nonsteroidal anti-inflammatory drug-based GSMs have different mechanisms of action with regard to Notch processing because Tarenflurbil ((R) )-Flurbiprofen, a well-known nonsteroidal anti-inflammatory drug, affects only Aβ and does not affect Notch β formation[2].
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| ln Vivo |
In C57BL6/J mice that develop a non-remitting form of the disease and in SJL mice that develop a relapsing-remitting (RR)-EAE, the effects of both an early and late start of treatment with Tarenflurbil ((R)-Flurbiprofen) are evaluated. When administered within three days of immunization, tartenflurbil ((R)-Flurbiprofen) totally prevents the development of clinical EAE scores in C57BL6/J mice. We call this regimen "preventive treatment." Since the effect is dose-dependent, 5 mg/kg/day is the minimal daily dose required for full prevention. The positive control, Fingolimod (FTY720, 0.5 mg/kg/day), has effects similar to those of Tarenflurbil ((R)-Flurbiprofen). In C57BL6/J mice, tareflurbil ((R)-Flurbiprofen) also significantly lowers clinical EAE scores when treatment is started just prior to the onset of clinical manifestations, a strategy known as semi-therapeutic (10 mg/kg/day), and when treatment is started on day 13 (5 mg/g/day), after the disease has fully developed[3].
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Flurbiprofen has known human metabolites that include (2S,3S,4S,5R)-6-[(2R)-2-(3-fluoro-4-phenylphenyl)propanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid. |
| References |
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| Additional Infomation |
(R)-flurbiprofen is a flurbiprofen. It is an enantiomer of a (S)-flurbiprofen.
Tarenflurbil is an investigational drug that was studied in patients with mild Alzheimer's disease. It is a selective amyloid lowering agent (SALA) that reduces levels of the toxic peptide amyloid beta 42 (Aβ42) in cultured human cells and in animal models. Aβ42 is the primary initiator of neurotoxicity and amyloid plaque development in the brains of Alzheimer's disease patients. In June 2008 development of the drug for Alzheimer's disease was discontinued. Tarenflurbil has also been used in trials studying the treatment of Prostate Cancer. Tarenflurbil is an orally active synthetic enantiomer of flurbiprofen. Tarenflurbil activates c-Jun N terminal kinase, increases AP-1 binding to DNA, and downregulates cyclin D1 expression, resulting in arrest of tumor cells in the G1 phase of the cell cycle and apoptosis. This agent also affects the expression of nuclear factor kappa B, a rapid response transcription factor that stimulates the immune response to tumor cells. R-flurbiprofen does not inhibit the enzyme cyclo-oxygenase. Drug Indication Investigated for use/treatment in alzheimer's disease and prostate cancer. Mechanism of Action MPC-7869 is not an inhibitor of cyclooxygenase enzymes (COX-1 and COX-2). The compound modulates the signal transduction and transcription activation pathways associated with nuclear factor kappaB (NFkappaB), a principle transcription factor in the expression of many molecules involved in cell growth, cell death and inflammation. In addition, MPC-7869 has recently been shown to modulate gamma-secretase and selectively lower levels of Abeta42 peptide in vitro and in vivo, and to reduce amyloid pathology in the brain. MPC-7869 has an excellent safety profile and is very potent in animal models of cancer and Alzheimer's disease. In transgenic mouse studies, MPC-7869 reduced brain amyloid levels and prevented memory loss. |
| Molecular Formula |
C15H13FO2
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|---|---|
| Molecular Weight |
244.26
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| Exact Mass |
244.089
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| CAS # |
51543-40-9
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| Related CAS # |
Flurbiprofen;5104-49-4
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| PubChem CID |
92337
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
376.2±30.0 °C at 760 mmHg
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| Melting Point |
110-113ºC
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| Flash Point |
181.3±24.6 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.568
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| LogP |
4.11
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
18
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| Complexity |
286
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C[C@H](C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O
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| InChi Key |
SYTBZMRGLBWNTM-SNVBAGLBSA-N
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| InChi Code |
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)/t10-/m1/s1
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| Chemical Name |
(2R)-2-(3-fluoro-4-phenylphenyl)propanoic acid
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| Synonyms |
(R)-Flurbiprofen; E 7869; MPC 7869; E-7869; MPC7869; E7869; Flurizan; Furbiprofen; MPC-7869;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 50 mg/mL (~204.70 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (10.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0940 mL | 20.4700 mL | 40.9400 mL | |
| 5 mM | 0.8188 mL | 4.0940 mL | 8.1880 mL | |
| 10 mM | 0.4094 mL | 2.0470 mL | 4.0940 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02206854 | COMPLETED | Drug: R-flurbiprofen | Healthy Volunteers | Gerd Geisslinger | 2014-06 | Phase 1 |
| NCT00322036 | TERMINATED | Drug: MPC-7869 Drug: MPC-7869 |
Alzheimer Disease Dementia |
Myrexis Inc. | 2006-05 | Phase 3 |
| NCT00045123 | UNKNOWN STATUS | Drug: tarenflurbil Procedure: adjuvant therapy |
Prostate Cancer | Myrexis Inc. | 2002-02 | Phase 2 |
| NCT00105547 | COMPLETED | Drug: MPC-7869 Drug: MPC-7869 |
Alzheimer Disease Dementia |
Myrexis Inc. | 2005-02 | Phase 3 |
| NCT00380276 | TERMINATED | Drug: MPC-7869 | Alzheimer's Disease | Myrexis Inc. | 2006-09 | Phase 3 |
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