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S2064

Sigma-Aldrich

SC-560

≥98% (HPLC)

Synonym(s):

5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-trifluoromethyl pyrazole

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About This Item

Empirical Formula (Hill Notation):
C17H12ON2ClF3
CAS Number:
188817-13-2
Molecular Weight:
352.74
MDL number:
MFCD02179214
UNSPSC Code:
51111800
PubChem Substance ID:
24278696
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)-n2nc(cc2-c3ccc(Cl)cc3)C(F)(F)F

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

InChI key

PQUGCKBLVKJMNT-UHFFFAOYSA-N

Gene Information

human ... PTGS1(5742) , PTGS2(5743)

Application

SC-560 has been used as a cyclooxygenase-1 (COX-1) inhibitor to study its effects on prostaglandin E-2 (PGE2) signaling in ciliogenesis in zebrafish embryos. It has also been used as a selective inhibitor of COX-1 to study its role in PM10-induced endothelial dysfunction.

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.
SC-560 belongs to the diaryl heterocycle class of cyclooxygenase (COX) inhibitors. It exhibits anti-tumor and anti-proliferative activities.
Selective cyclooxygenase-1 (COX-1) inhibitor, exhibiting 700-fold selectivity for COX-1 over COX-2.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dan Wang et al.
Antioxidants (Basel, Switzerland), 11(5) (2022-05-29)
Nuclear factor erythroid factor E2-related factor 2 (Nrf2) transcribes antioxidant genes that reduce the blood pressure (BP), yet its activation with tert-butylhydroquinone (tBHQ) in mice infused with angiotensin II (Ang II) increased mean arterial pressure (MAP) over the first 4
Anti-bovine viral diarrhoea virus and hepatitis C virus activity of the cyclooxygenase inhibitor SC-560
Okamoto M, et al.
Antiviral Chemistry & Chemotherapy, 20(1), 47-54 (2009)
Cyclooxygenase-1 (COX-1) and COX-1 inhibitors in cancer: a review of oncology and medicinal chemistry literature
Pannunzio A and Coluccia M
Pharmaceuticals (Basel, Switzerland), 11(4), 101-101 (2018)
Alessandra Pannunzio et al.
Pharmaceuticals (Basel, Switzerland), 11(4) (2018-10-14)
Prostaglandins and thromboxane are lipid signaling molecules deriving from arachidonic acid by the action of the cyclooxygenase isoenzymes COX-1 and COX-2. The role of cyclooxygenases (particularly COX-2) and prostaglandins (particularly PGE₂) in cancer-related inflammation has been extensively investigated. In contrast
Formulation dependent pharmacokinetics, bioavailability and renal toxicity of a selective cyclooxygenase-1 inhibitor SC-560 in the rat
Teng XW, et al.
Toxicology and Applied Pharmacology, 272(1), 205-210 (2003)
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