FlurbiprofenA potent inhibitor of Cox-1 and Cox-2

Flurbiprofen (CAS 5104-49-4)

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Sinónimo: Ansaid
Solicitud: A potent inhibitor of Cox-1 and Cox-2
Número de CAS: 5104-49-4
Pureza: ≥98%
Peso Molecular: 244.3
Fórmula Molecular: C15H13FO2
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Flurbiprofen is a mixture of S(+) and R(-) enantiomers. Flurbiprofen is a cell-permeable, non-steroidal anti-inflammatory (NSAID) agent that acts as a potent inhibitor of Cox-1 (cyclooxygenase-1) and Cox-2 (cyclooxygenase-2) (IC50 = 5 nM for LPS-induced Cox in human peripheral blood cells). The S(+) enantiomer is reported to be more potent as a Cox-2 inhibitor than the R(-) enantiomer. Flurbiprofen suppresses iNOS expression in RAW 264.7 macrophages. It reduces Aβ loads and Congo Red staining in APP+PS1 transgenic mice.


References

1. Karmali, R A., et al., 1986. Antitumor activity in a rat mammary adenocarcinoma: the effect of cyclooxygenase inhibitors and immunization against prostaglandin E2. Prostaglandins, leukotrienes, and medicine. 23(1): 11-4. PMID: 3090559
2. Karmali, R A., et al., 1985. Antitumor activity in a rat mammary adenocarcinoma: the effect of cyclooxygenase inhibitors and immunization against prostaglandin E2. Prostaglandins, leukotrienes, and medicine. 20(3): 283-6. PMID: 3937158
3. Curnock, A P., et al., 1997. Potencies of leflunomide and HR325 as inhibitors of prostaglandin endoperoxide H synthase-1 and -2: comparison with nonsteroidal anti-inflammatory drugs. The Journal of pharmacology and experimental therapeutics. 282(1): 339-47. PMID: 9223572
4. Wechter, W J., et al., 1997. R-flurbiprofen chemoprevention and treatment of intestinal adenomas in the APC(Min)/+ mouse model: implications for prophylaxis and treatment of colon cancer. Cancer research. 57(19): 4316-24. PMID: 9331093
5. Riendeau, D., et al., 1997. Comparison of the cyclooxygenase-1 inhibitory properties of nonsteroidal anti-inflammatory drugs (NSAIDs) and selective COX-2 inhibitors, using sensitive microsomal and platelet assays. Canadian journal of physiology and pharmacology. 75(9): 1088-95. PMID: 9365818
6. Klabunde, T., et al., 2000. Rational design of potent human transthyretin amyloid disease inhibitors. Nature structural biology. 7(4): 312-21. PMID: 10742177
7. Range, S P., et al., 2000. Selectivity of cyclo-oxygenase inhibitors in human pulmonary epithelial and smooth muscle cells. The European respiratory journal. 15(4): 751-6. PMID: 10780769
8. van Haeringen, N J., et al., 2000. Constitutive cyclooxygenase-1 and induced cyclooxygenase-2 in isolated human iris inhibited by S(+) flurbiprofen. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 16(4): 353-61. PMID: 10977131
9. Jantzen, Paul T., et al., 2002. Microglial activation and beta -amyloid deposit reduction caused by a nitric oxide-releasing nonsteroidal anti-inflammatory drug in amyloid precursor protein plus presenilin-1 transgenic mice. The Journal of neuroscience : the official journal of the Society for Neuroscience. 22(6): 2246-54. PMID: 11896164

Estado de Materia :
Solid
Solubilidad :
Soluble in DMSO (50 mg/ml), methanol (50 mg/ml), ethanol (~100 mg/ml), DMF (~100 mg/ml), and buffers of ionic strength ≥0.1 M and pH ≥7.4 (~5 mg/ml). Insoluble in water.
ALMACENAMIENTO :
Store at room temperature
Punto de Fusión :
110-112° C (lit.)
Punto de ebullición :
376.23° C at 760 mmHg (Predicted)
Densidad :
1.2 g/cm3 (Predicted)
Indice de Refracción :
n20D 1.57 (Predicted)
IC50 :
LPS-induced COX: IC50 = 5 nM (human peripheral blood cells); COX-2: IC50 = 0.51 µM (human); COX-1: IC50 = 0.04 µM (human)
Valores de pK :
pKa: 4.14
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
WGK Alemania :
3
RTECS :
DU8341000
PubChem CID :
3394
Indice de Merck :
14: 4199
Número MDL :
MFCD00079303
Número EC :
225-827-6
SMILES :
CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O

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