D7196

2,5-Dimethyl-Celecoxib

≥98% (HPLC)

• Synonym(e): 4-[5-(2,5-Dimethylphenyl)-3-(trifluormethyl)-1H-pyrazol-1-yl]-benzolsulfonamid
• Empirische Formel (Hill-System): C₁₈H₁₆F₃N₃O₂S
• CAS-Nummer: 457639-26-8
• Molekulargewicht: 395.40
• MDL-Nummer: MFCD19443858
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 329798845
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥98% (HPLC)
• Form: powder
• Farbe: white to beige
• Löslichkeit: DMSO: 20 mg/mL, clear
• Lagertemp.: room temp
• SMILES String: Cc1ccc(C)c(c1)-c2cc(nn2-c3ccc(cc3)S(N)(=O)=O)C(F)(F)F
• InChI: 1S/C18H16F3N3O2S/c1-11-3-4-12(2)15(9-11)16-10-17(18(19,20)21)23-24(16)13-5-7-14(8-6-13)27(22,25)26/h3-10H,1-2H3,(H2,22,25,26)
• InChIKey: NTFOSUUWGCDXEF-UHFFFAOYSA-N

Beschreibung

Anwendung

2,5-Dimethyl-celecoxib has been used

• To block the synthesis of prostaglandin E2 and to study effect of transforming growth factor-2 signaling towards cyclooxygenase-2 expression.
• In an in vitro study to analyze its pro-oxidative capacities in metastatic melanoma/ breast cancer cells.
• To study its interaction between silymarin on chemically induced osteoarthritis in rats.

Biochem./physiol. Wirkung

Celecoxib is a pyrazole derivative containing sulfonamide substituent. It is mostly metabolized by the cytochrome P450 2C9 system. Celecoxib possess anti-inflammatory action and can enhance antidepressant response.

Celecoxib, and the inactive analog 2′,5′-dimethyl celecoxib both induce apoptosis in a many cancer cell lines by down-regulating the expression of survivin. This activiy is mediated via an AKT mediated pathway, and is unique to this class of cyclo-oxygenase inhibitors, as non-selective NSAIDs or other COX-2 specific inhibitors such as rofecoxib, do not effect survivin expression. Unlike celecoxib, 2′,5′-dimethyl celecoxib is devoid of any inhibitory activity against COX-2.

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H301
• P-Sätze: P264 - P270 - P301 + P310 - P405 - P501
• Gefahreneinstufungen: Acute Tox. 3 Oral
• Lagerklassenschlüssel: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3