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AB144471

(R)-Flurbiprofen (Tarenflurbil), gamma-secretase inhibitor

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MW 244.26 Da, Purity >99%. γ-secretase inhibitor. Flurbiprofen (ab142877) enantiomer. Inactive towards COX. Inhibits NF-κB and AP-1 activation. Prevents Aβ42 formation and shows anti-inflammatory and neuroprotective effects in vivo. Orally active.

View Alternative Names

(R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, CP2CJ_HUMAN, CPCJ, CYP2C, CYP2C19, CYPIIC17, CYPIIC19, Cyclooxygenase, Cyclooxygenase 2b, Cyclooxygenase-2, Cytochrome P-450 II C, Cytochrome P450 2C19, Cytochrome P450, subfamily IIC (mephenytoin 4-hydroxylase), polypeptide 19, Cytochrome P450-11A, Cytochrome P450-254C, EC 1.14.99.1, GRIPGHS, Glucocorticoid-regulated inflammatory Prostaglandin G/H synthase, Glucocorticoid-regulated inflammatory cyclooxygenase, Macrophage activation-associated marker protein P71/73, Mephenytoin 4-hydroxylase, Microsomal monooxygenase, OTTHUMP00000033524, P450-11A, P450C2C, PES-2, PGG/HS, PGH synthase 2, PGH2_HUMAN, PGHS-2, PHS 2, PHS II, PTGS2, Prostaglandin G/H synthase, Prostaglandin G/H synthase 2, Prostaglandin G/H synthase 2 precursor, Prostaglandin G/H synthase and cyclooxygenase, Prostaglandin H2 synthase 2, Prostaglandin-endoperoxide synthase 2, S-mephenytoin 4-hydroxylase, TIS10, TIS10 protein, Xenobiotic monooxygenase, fj02a10, flavoprotein-linked monooxygenase, hCox 2, prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase), ptgs2a, unp1239, wu:fj02a10

Key facts

CAS number

51543-40-9

Purity

>99%

Form

Solid

form

Molecular weight

244.26 Da

Molecular formula

C<sub>1</sub><sub>5</sub>H<sub>1</sub><sub>3</sub>FO<sub>2</sub>

PubChem

92337

Nature

Synthetic

Solubility

Soluble in ethanol to 100 mM

Soluble in DMSO to 25 mM

Biochemical name

Tarenflurbil

Biological description

γ-secretase inhibitor. Flurbiprofen (ab142877) enantiomer. Inactive towards COX. Inhibits NF-κB and AP-1 activation. Prevents Aβ42 formation and shows anti-inflammatory and neuroprotective effects in vivo. Orally active.

Canonical smiles

CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O

Isomeric smiles

C[C@H](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)/t10-/m1/s1

InChiKey

SYTBZMRGLBWNTM-SNVBAGLBSA-N

IUPAC Name

(2R)-2-(3-fluoro-4-phenylphenyl)propanoic acid

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months
Handling instructions

Need more advice on solubility, usage and handling? Please visit our our product support page for more details.

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Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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Toxic, refer to SDS for further information.

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

COX2 also known as Cyclooxygenase 2 and Cytochrome P450 2C19 is an enzyme that has mass approximately 72 kDa. It plays a vital role in converting arachidonic acid to prostaglandins which are lipid compounds that have hormone-like effects. COX2 is inducible and prominently expressed in sites of inflammation epithelial tissues and some cancers. It is not usually present in most normal tissues but becomes highly expressed in response to inflammatory stimuli.
Biological function summary

COX2 is involved in generating prostaglandins influencing inflammation pain and fever response. The enzyme does not typically act alone; it often associates as part of a larger complex that includes other signaling molecules that regulate the conversion of unsaturated fatty acids. This conversion results in substances that can modulate cellular activities such as vasodilation and cellular proliferation. COX2's biological activity links to various body processes that manage inflammation and healing.

Pathways

COX2 is an important enzyme in the prostaglandin biosynthesis pathway and the inflammatory response pathway. Its activity contributes significantly to the biosynthesis of prostanoids which include prostaglandins and thromboxanes. COX2 interacts with and is regulated by inflammatory and mitogenic signals. It shares roles in these pathways with enzymes like COX1 and it often works in concert with phospholipase A2 which releases arachidonic acid for conversion into prostaglandins.

COX2 is notably implicated in inflammatory diseases such as arthritis and plays a role in cancer where its expression is upregulated. The inflammatory processes it facilitates can exacerbate arthritis symptoms making it a target for nonsteroidal anti-inflammatory drugs like ibuprofen and flurbiprofen. In cancer COX2 is associated with increased angiogenesis and tumor growth. The enzyme's pathway intersects with proteins like matrix metalloproteinases in these disease states showing its role in tissue remodeling and neoplastic progression.

Product protocols

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