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188817-13-2

188817-13-2 Structure

188817-13-2 Structure
IdentificationBack Directory
[Name]

SC-560
[CAS]

188817-13-2
[Synonyms]

SC SC
SC-560
CS-1042
5-(4-Chlorophenyl)
SC-560;SC 560;SC560
SC-560 Assay Reagent
SC-560 - CAS 188817-13-2 - Calbiochem
5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)-3-TRIFLUOROMETHYLPYRAZOLE
5-(4-Chlorophenyl)-3-(trifluoromethyl)-1-(4-methoxyphenyl)-1H-pyrazole
5-(4-CHLOROPHENYL)-1-(4-METHOXYPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE
1H-Pyrazole, 5-(4-chlorophenyl)-1-(4-Methoxyphenyl)-3-(trifluoroMethyl)-
[Molecular Formula]

C17H12ClF3N2O
[MDL Number]

MFCD02179214
[MOL File]

188817-13-2.mol
[Molecular Weight]

352.74
Chemical PropertiesBack Directory
[Melting point ]

63 °C
[Boiling point ]

440.6±45.0 °C(Predicted)
[density ]

1.33
[storage temp. ]

2-8°C
[solubility ]

DMSO: >20mg/mL
[form ]

Off-white solid
[pka]

-3?+-.0.10(Predicted)
[color ]

White to Light yellow to Light orange
[InChI]

1S/C17H12ClF3N2O/c1-24-14-8-6-13(7-9-14)23-15(10-16(22-23)17(19,20)21)11-2-4-12(18)5-3-11/h2-10H,1H3
[InChIKey]

PQUGCKBLVKJMNT-UHFFFAOYSA-N
[SMILES]

COc1ccc(cc1)-n2nc(cc2-c3ccc(Cl)cc3)C(F)(F)F
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36
[WGK Germany ]

3
[HS Code ]

2933199090
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

Selective COX-1 inhibitor (IC50=9nM). Shows 700-fold more selectivity over COX-2 (IC50=6.3μM). Inhibits COX-1-derived platelet thromboxane B2, gastric PGE2, and dermal PGE2 production. Orally active in rat.
[Definition]

ChEBI: A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-methoxyphenyl, trifluoromethyl and 4-chlorophenyl groups, respectively. Unlike many members of the diaryl heterocycle class of cyclo xygenase (COX) inhibitors, SC-560 is selective for COX-1.
[Biological Activity]

Highly selective cyclooxygenase-1 (COX-1) inhibitor (IC 50 values are 0.009 and 6.3 μ M for COX-1 and COX-2 respectively). Inhibits COX-1-derived platelet thromboxane B 2 , gastric PGE 2 and dermal PDE 2 production. Significantly reduces ovarian surface epithelial tumor growth in vivo . Orally active.
[Biochem/physiol Actions]

SC-560 (5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole) is a non-steroidal anti-inflammatory drug (NSAID). It is a lipophilic, diaryl heterocyclic compound. SC-560 acts as an effective antiviral agent against hepatitis C virus (HCV). It also has a potential to hinder prostaglandin E2 synthesis in neurons at nanomolar concentrations.
[in vitro]

preincubation of cox-1 with sc-560 inhibited the conversion of arachidonic acid to pge2 in a concentration-dependent manner [1]. sc-560 was necessary to sustain a reduced basal level of pgi2 for an extended period. sc-560 inhibits cell proliferation and accelerates apoptosis which results in attenuated tumor growth [2].
[in vivo]

oral dosing with either 10 or 30 mg/kg sc-560 1 hr before assay completely inhibited cox-1-derived platelet thromboxane b2, gastric pge2, and dermal pge2 production [1]. sc-560 can suppress ovarian surface epithelial tumor growth. tumor growth was suppressed in allografted mice treated with sc-560 for a longer period, but the reduction in tumor growth was less dramatic than the short-term treated [2].
[IC 50]

0.009 μm for cox-1; 6.3 μm for cox-2
[storage]

Store at +4°C
[References]

[1] daikoku t, wang d, tranguch s, morrow jd, orsulic s, dubois rn, dey sk. cyclooxygenase-1 is a potential target for prevention and treatment of ovarian epithelial cancer. cancer res. 2005 may 1;65(9):3735-44.
[2] christopher j. smith, yan zhang, carol m. koboldt, jerry muhammad, ben s. zweifel, alex shaffer, john j. talley, jaime l. masferrer, karen seibert, peter c. isakson. pharmacological analysis of cyclooxygenase-1 in inflammation. proc natl acad sci u s a. 1998 oct 27; 95(22): 13313–13318.
Spectrum DetailBack Directory
[Spectrum Detail]

SC-560(188817-13-2)1HNMR
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