SC-58125 | CAS#162054-19-5 | COX-2 inhibitor

MedKoo Cat#: 563403 | Name: SC-58125

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SC-58125 is a selective cyclooxygenase 2 (COX-2) inhibitor. SC-58125 exhibits antitumor activity and can inhibit edema at the inflammatory site and has analgesic effect.

Chemical Structure

SC-58125

CAS#162054-19-5

Theoretical Analysis

MedKoo Cat#: 563403

Name: SC-58125

CAS#: 162054-19-5

Chemical Formula: C17H12F4N2O2S

Exact Mass: 384.0556

Molecular Weight: 384.34

Elemental Analysis: C, 53.13; H, 3.15; F, 19.77; N, 7.29; O, 8.33; S, 8.34

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00
10mg	USD 500.00
25mg	USD 800.00

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Synonym

SC-58125; SC 58125; SC58125;

IUPAC/Chemical Name

5-(4-Fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3(trifluoromethyl)-1H-pyrazole

InChi Key

JHBIMJKLBUMNAU-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H12F4N2O2S/c1-26(24,25)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

SMILES Code

FC(C1=NN(C2=CC=C(S(=O)(C)=O)C=C2)C(C3=CC=C(F)C=C3)=C1)(F)F

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SC-58125 is a COX-2 inhibitor with an IC50 of 0.04 μM.

In vitro activity:

SC-58125 exposure reduces malignant human B-cell lymphomas and chronic lymphocytic leukemia B-cells survival. SC-58125 decreased intracellular glutathione (GSH) content in malignant human B-cells and in Cox-2 deficient mouse B-cells. SC-58125 significantly increased B-cell reactive oxygen species production. The SC-58125-mediated GSH depletion resulted in elevated steady-state levels of the glutamate cysteine ligase catalytic subunit mRNA and protein. Reference: Cancer Immunol Immunother. 2008 Mar;57(3):347-58. https://pubmed.ncbi.nlm.nih.gov/17668203/

In vivo activity:

This study concluded that SC-58125 primarily exerts a cytostatic effect in human colon carcinoma cells in nude mice. Treatment with SC-58125 attenuated tumor growth for up to 15 days by delaying progression through the cell cycle at the G(2)/M transition. Accordingly, p34(cdc2) protein levels and activity were decreased following SC-58125 treatment. Reference: Neoplasia. 2001 Sep-Oct;3(5):428-36. https://pubmed.ncbi.nlm.nih.gov/11687954/

	Solvent	mg/mL	mM
Solubility
	DMSO	250.0	650.45

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 384.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Ryan EP, Bushnell TP, Friedman AE, Rahman I, Phipps RP. Cyclooxygenase-2 independent effects of cyclooxygenase-2 inhibitors on oxidative stress and intracellular glutathione content in normal and malignant human B-cells. Cancer Immunol Immunother. 2008 Mar;57(3):347-58. doi: 10.1007/s00262-007-0374-4. Epub 2007 Aug 1. PMID: 17668203. 2. Ding J, Chang Q, Gong S. Inhibitory effects of Celecoxib and Sc-58125 on proliferation of human carcinoma of larynx Hep-2 in vitro. J Huazhong Univ Sci Technolog Med Sci. 2005;25(2):202-5. doi: 10.1007/BF02873577. PMID: 16116973. 3. Yu Y, Jiang J. COX-2/PGE2 axis regulates hippocampal BDNF/TrkB signaling via EP2 receptor after prolonged seizures. Epilepsia Open. 2020 Jun 9;5(3):418-431. doi: 10.1002/epi4.12409. PMID: 32913950; PMCID: PMC7469770. 4. Williams CS, Sheng H, Brockman JA, Armandla R, Shao J, Washington MK, Elkahloun AG, DuBois RN. A cyclooxygenase-2 inhibitor (SC-58125) blocks growth of established human colon cancer xenografts. Neoplasia. 2001 Sep-Oct;3(5):428-36. doi: 10.1038/sj.neo.7900177. PMID: 11687954; PMCID: PMC1506203.

In vitro protocol:

In vivo protocol:

1. Yu Y, Jiang J. COX-2/PGE2 axis regulates hippocampal BDNF/TrkB signaling via EP2 receptor after prolonged seizures. Epilepsia Open. 2020 Jun 9;5(3):418-431. doi: 10.1002/epi4.12409. PMID: 32913950; PMCID: PMC7469770. 2. Williams CS, Sheng H, Brockman JA, Armandla R, Shao J, Washington MK, Elkahloun AG, DuBois RN. A cyclooxygenase-2 inhibitor (SC-58125) blocks growth of established human colon cancer xenografts. Neoplasia. 2001 Sep-Oct;3(5):428-36. doi: 10.1038/sj.neo.7900177. PMID: 11687954; PMCID: PMC1506203.

1: Shuey MM, Xiang RR, Moss ME, Carvajal BV, Wang Y, Camarda N, Fabbri D, Rahman P, Ramsey J, Stepanian A, Sebastiani P, Wells QS, Beckman JA, Jaffe IZ. Systems Approach to Integrating Preclinical Apolipoprotein E-Knockout Investigations Reveals Novel Etiologic Pathways and Master Atherosclerosis Network in Humans. Arterioscler Thromb Vasc Biol. 2022 Jan;42(1):35-48. doi: 10.1161/ATVBAHA.121.317071. Epub 2021 Nov 11. PMID: 34758633; PMCID: PMC8887835. 2: Yu Y, Jiang J. COX-2/PGE2 axis regulates hippocampal BDNF/TrkB signaling via EP2 receptor after prolonged seizures. Epilepsia Open. 2020 Jun 9;5(3):418-431. doi: 10.1002/epi4.12409. PMID: 32913950; PMCID: PMC7469770. 3: Vo N, Couch B, Lee J, Sowa G, Kang J, Rebecca S. Actions of Prostaglandins on Human Nucleus Pulposus Metabolism Inferred by Cyclooxygenase 2 Inhibition of Cytokine Activated Cells. Neurospine. 2020 Mar;17(1):60-68. doi: 10.14245/ns.2040050.025. Epub 2020 Mar 31. PMID: 32252155; PMCID: PMC7136088. 4: Danilov A, Shaposhnikov M, Shevchenko O, Zemskaya N, Zhavoronkov A, Moskalev A. Influence of non-steroidal anti-inflammatory drugs on Drosophila melanogaster longevity. Oncotarget. 2015 Aug 14;6(23):19428-44. doi: 10.18632/oncotarget.5118. PMID: 26305987; PMCID: PMC4637296. 5: Al-Husseini A, Wijesinghe DS, Farkas L, Kraskauskas D, Drake JI, Van Tassel B, Abbate A, Chalfant CE, Voelkel NF. Increased eicosanoid levels in the Sugen/chronic hypoxia model of severe pulmonary hypertension. PLoS One. 2015 Mar 18;10(3):e0120157. doi: 10.1371/journal.pone.0120157. PMID: 25785937; PMCID: PMC4364907. 6: Misra UK, Pizzo SV. Evidence for a pro-proliferative feedback loop in prostate cancer: the role of Epac1 and COX-2-dependent pathways. PLoS One. 2013 Apr 30;8(4):e63150. doi: 10.1371/journal.pone.0063150. PMID: 23646189; PMCID: PMC3640024. 7: Montaño LM, Carbajal V, Vargas MH, García-Hernández LM, Díaz-Hernández V, Checa M, Barajas-López C. Histamine, carbachol, and serotonin induce hyperresponsiveness to ATP in guinea pig tracheas: involvement of COX-2 pathway. Pflugers Arch. 2013 Aug;465(8):1171-9. doi: 10.1007/s00424-013-1253-9. Epub 2013 Mar 10. PMID: 23475395. 8: Bernard JJ, Gallo RL. Cyclooxygenase-2 enhances antimicrobial peptide expression and killing of Staphylococcus aureus. J Immunol. 2010 Dec 1;185(11):6535-44. doi: 10.4049/jimmunol.1002009. Epub 2010 Oct 22. PMID: 20971925; PMCID: PMC3025174. 9: Bernard MP, Phipps RP. Inhibition of cyclooxygenase-2 impairs the expression of essential plasma cell transcription factors and human B-lymphocyte differentiation. Immunology. 2010 Jan;129(1):87-96. doi: 10.1111/j.1365-2567.2009.03152.x. PMID: 20050331; PMCID: PMC2807489. 10: Ryan EP, Bushnell TP, Friedman AE, Rahman I, Phipps RP. Cyclooxygenase-2 independent effects of cyclooxygenase-2 inhibitors on oxidative stress and intracellular glutathione content in normal and malignant human B-cells. Cancer Immunol Immunother. 2008 Mar;57(3):347-58. doi: 10.1007/s00262-007-0374-4. Epub 2007 Aug 1. PMID: 17668203; PMCID: PMC11031111. 11: Zhang J, Xu ZQ, Hu Q, Qiu XW, Wang ZR. [Effects of selective cyclooxygenase-2 inhibitor on proliferation and apoptosis of human bladder cancer cell line T24]. Ai Zheng. 2007 Apr;26(4):377-81. Chinese. PMID: 17430655. 12: Ryan EP, Malboeuf CM, Bernard M, Rose RC, Phipps RP. Cyclooxygenase-2 inhibition attenuates antibody responses against human papillomavirus-like particles. J Immunol. 2006 Dec 1;177(11):7811-9. doi: 10.4049/jimmunol.177.11.7811. PMID: 17114452. 13: Matsunaga A, Kawamoto M, Shiraishi S, Yasuda T, Kajiyama S, Kurita S, Yuge O. Intrathecally administered COX-2 but not COX-1 or COX-3 inhibitors attenuate streptozotocin-induced mechanical hyperalgesia in rats. Eur J Pharmacol. 2007 Jan 5;554(1):12-7. doi: 10.1016/j.ejphar.2006.09.072. Epub 2006 Oct 20. PMID: 17112505. 14: Piazuelo E, Jiménez P, Strunk M, Santander S, García A, Esteva F, Lanas A. Effects of selective PGE2 receptor antagonists in esophageal adenocarcinoma cells derived from Barrett's esophagus. Prostaglandins Other Lipid Mediat. 2006 Dec;81(3-4):150-61. doi: 10.1016/j.prostaglandins.2006.09.002. Epub 2006 Oct 6. PMID: 17085323. 15: Ye Y, Lin Y, Atar S, Huang MH, Perez-Polo JR, Uretsky BF, Birnbaum Y. Myocardial protection by pioglitazone, atorvastatin, and their combination: mechanisms and possible interactions. Am J Physiol Heart Circ Physiol. 2006 Sep;291(3):H1158-69. doi: 10.1152/ajpheart.00096.2006. Epub 2006 Apr 7. PMID: 16603698. 16: Candelario-Jalil E, Akundi RS, Bhatia HS, Lieb K, Appel K, Muñoz E, Hüll M, Fiebich BL. Ascorbic acid enhances the inhibitory effect of aspirin on neuronal cyclooxygenase-2-mediated prostaglandin E2 production. J Neuroimmunol. 2006 May;174(1-2):39-51. doi: 10.1016/j.jneuroim.2006.01.003. Epub 2006 Mar 10. PMID: 16529823. 17: Kuge Y, Katada Y, Shimonaka S, Temma T, Kimura H, Kiyono Y, Yokota C, Minematsu K, Seki K, Tamaki N, Ohkura K, Saji H. Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression. Nucl Med Biol. 2006 Jan;33(1):21-7. doi: 10.1016/j.nucmedbio.2005.10.004. PMID: 16459255. 18: Ding J, Tsuboi K, Hoshikawa H, Goto R, Mori N, Katsukawa M, Hiraki E, Yamamoto S, Abe M, Ueda N. Cyclooxygenase isozymes are expressed in human myeloma cells but not involved in anti-proliferative effect of cyclooxygenase inhibitors. Mol Carcinog. 2006 Apr;45(4):250-9. doi: 10.1002/mc.20175. PMID: 16385588. 19: Atar S, Ye Y, Lin Y, Freeberg SY, Nishi SP, Rosanio S, Huang MH, Uretsky BF, Perez-Polo JR, Birnbaum Y. Atorvastatin-induced cardioprotection is mediated by increasing inducible nitric oxide synthase and consequent S-nitrosylation of cyclooxygenase-2. Am J Physiol Heart Circ Physiol. 2006 May;290(5):H1960-8. doi: 10.1152/ajpheart.01137.2005. Epub 2005 Dec 9. PMID: 16339820. 20: Ding J, Chang Q, Gong S. Inhibitory effects of Celecoxib and Sc-58125 on proliferation of human carcinoma of larynx Hep-2 in vitro. J Huazhong Univ Sci Technolog Med Sci. 2005;25(2):202-5. doi: 10.1007/BF02873577. PMID: 16116973.