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MedKoo Cat#: 527888 | Name: CAY10404
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Description:

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

CAY10404 is one of the most selective inhibitors of COX-2 over COX-1.

Chemical Structure

CAY10404
CAY10404
CAS#340267-36-9

Theoretical Analysis

MedKoo Cat#: 527888

Name: CAY10404

CAS#: 340267-36-9

Chemical Formula: C17H12F3NO3S

Exact Mass: 367.0490

Molecular Weight: 367.34

Elemental Analysis: C, 55.58; H, 3.29; F, 15.52; N, 3.81; O, 13.07; S, 8.73

Price and Availability

Size Price Availability Quantity
50mg USD 550.00 2 Weeks
100mg USD 950.00 2 Weeks
200mg USD 1,450.00 2 Weeks
500mg USD 2,450.00 2 Weeks
1g USD 3,650.00 2 Weeks
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Related CAS #
No Data
Synonym
CAY 10404; CAY-10404; CAY10404
IUPAC/Chemical Name
3-[4-(Methylsulfonyl)phenyl]-4-phenyl-5-(trifluoromethyl)-isoxazole
InChi Key
KKBWWVXRKULXHF-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H12F3NO3S/c1-25(22,23)13-9-7-12(8-10-13)15-14(11-5-3-2-4-6-11)16(24-21-15)17(18,19)20/h2-10H,1H3
SMILES Code
FC(C1=C(C2=CC=CC=C2)C(C3=CC=C(S(=O)(C)=O)C=C3)=NO1)(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
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
CAY10404 is a potent and selective cyclooxygenase-2 (COX-2) inhibitor with an IC50 of 1 nM and a selectivity index (SI; COX-1 IC50/COX-2 IC50) of >500000.
In vitro activity:
Treatment with CAY10404 in the range of 10-100 microM caused dose-dependent growth inhibition, with an average 50% inhibitory concentration (IC(50)) of 60-100 micromol/L, depending on the cell line. Western blot analysis of CAY10404-treated cells showed cleavage of poly (ADP-ribose) polymerase (PARP) and procaspase-3, signifying caspase activity and apoptotic cell death. CAY10404 treatment inhibited the phosphorylation of Akt, glycogen synthase kinase-3beta and extracellular signal-regulated kinases 1/2 in H460 and H358 cells. Reference: Respirology. 2009 Aug;14(6):850-8. https://doi.org/10.1111/j.1440-1843.2009.01563.x
In vivo activity:
The objective was to determine the role of cyclooxygenase-2 in mechanical ventilation-induced lung injury and the effects of cyclooxygenase-2 inhibition on lung inflammation and barrier disruption. Mice were mechanically ventilated at low and high tidal volumes, in the presence or absence of pharmacologic cyclooxygenase-2-specific inhibition with 3-(4-methylsulphonylphenyl)-4-phenyl-5-trifluoromethylisoxazole (CAY10404). Lung injury was assessed using markers of alveolar-capillary leakage and lung inflammation. Cyclooxygenase-2 expression and activity were measured by Western blotting, real-time PCR, and lung/plasma prostanoid analysis, and tissue sections were analyzed for cyclooxygenase-2 staining by immunohistochemistry. High tidal volume ventilation induced lung injury, significantly increasing both lung leakage and lung inflammation relative to control and low tidal volume ventilation. High tidal volume mechanical ventilation significantly induced cyclooxygenase-2 expression and activity, both in the lungs and systemically, compared with control mice and low tidal volume mice. The immunohistochemical analysis of lung sections localized cyclooxygenase-2 expression to monocytes and macrophages in the alveoli. The pharmacologic inhibition of cyclooxygenase-2 with CAY10404 significantly decreased cyclooxygenase activity and attenuated lung injury in mice ventilated at high tidal volume, attenuating barrier disruption, tissue inflammation, and inflammatory cell signaling. This study demonstrates the induction of cyclooxygenase-2 by mechanical ventilation, and suggests that the therapeutic inhibition of cyclooxygenase-2 may attenuate ventilator-induced acute lung injury. Reference: Am J Respir Cell Mol Biol. 2012 Sep;47(3):387-94. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/22556158/
Solvent mg/mL mM
Solubility
DMSO 100.0 272.23
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 367.34 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.

Recalculate based on batch purity %
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:
In vitro protocol:
1. Cho Y, Park MJ, Park M, Min SS, Yee J, Kim C, Han MS, Han SH. Effects of CAY10404 on the PKB/Akt and MAPK pathway and apoptosis in non-small cell lung cancer cells. Respirology. 2009 Aug;14(6):850-8. doi: 10.1111/j.1440-1843.2009.01563.x. PMID: 19703066.
In vivo protocol:
1. Robertson JA, Sauer D, Gold JA, Nonas SA. The role of cyclooxygenase-2 in mechanical ventilation-induced lung injury. Am J Respir Cell Mol Biol. 2012 Sep;47(3):387-94. doi: 10.1165/rcmb.2011-0005OC. Epub 2012 May 3. PMID: 22556158; PMCID: PMC3488687.
1: Lee H, Roshanravan H, Wang Y, Okamoto K, Ryu J, Shrivastav S, Qu P, Kopp JB. APOL1 renal risk variants induce aberrant THP-1 monocyte differentiation and increase eicosanoid production via enhanced expression of cyclooxygenase 2. Am J Physiol Renal Physiol. 2018 Jan 10. doi: 10.1152/ajprenal.00254.2017. [Epub ahead of print] PubMed PMID: 29357411. 2: 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. PubMed PMID: 26305987; PubMed Central PMCID: PMC4637296. 3: Liao K, Xia B, Zhuang QY, Hou MJ, Zhang YJ, Luo B, Qiu Y, Gao YF, Li XJ, Chen HF, Ling WH, He CY, Huang YJ, Lin YC, Lin ZN. Parthenolide inhibits cancer stem-like side population of nasopharyngeal carcinoma cells via suppression of the NF-κB/COX-2 pathway. Theranostics. 2015 Jan 1;5(3):302-21. doi: 10.7150/thno.8387. eCollection 2015. PubMed PMID: 25553117; PubMed Central PMCID: PMC4279193. 4: Bieniek J, Childress C, Swatski MD, Yang W. COX-2 inhibitors arrest prostate cancer cell cycle progression by down-regulation of kinetochore/centromere proteins. Prostate. 2014 Jul;74(10):999-1011. doi: 10.1002/pros.22815. Epub 2014 May 7. PubMed PMID: 24802614. 5: Yang Y, Shi J, Tolomelli G, Xu H, Xia J, Wang H, Zhou W, Zhou Y, Das S, Gu Z, Levasseur D, Zhan F, Tricot G. RARα2 expression confers myeloma stem cell features. Blood. 2013 Aug 22;122(8):1437-47. doi: 10.1182/blood-2013-02-482919. Epub 2013 Jul 11. PubMed PMID: 23847194; PubMed Central PMCID: PMC3750340. 6: Robertson JA, Sauer D, Gold JA, Nonas SA. The role of cyclooxygenase-2 in mechanical ventilation-induced lung injury. Am J Respir Cell Mol Biol. 2012 Sep;47(3):387-94. doi: 10.1165/rcmb.2011-0005OC. Epub 2012 May 3. PubMed PMID: 22556158; PubMed Central PMCID: PMC3488687. 7: Tajima T, Murata T, Aritake K, Urade Y, Michishita M, Matsuoka T, Narumiya S, Ozaki H, Hori M. EP2 and EP4 receptors on muscularis resident macrophages mediate LPS-induced intestinal dysmotility via iNOS upregulation through cAMP/ERK signals. Am J Physiol Gastrointest Liver Physiol. 2012 Mar 1;302(5):G524-34. doi: 10.1152/ajpgi.00264.2011. Epub 2011 Dec 8. PubMed PMID: 22159280; PubMed Central PMCID: PMC3311437. 8: Iwanaga K, Okada M, Murata T, Hori M, Ozaki H. Prostaglandin E2 promotes wound-induced migration of intestinal subepithelial myofibroblasts via EP2, EP3, and EP4 prostanoid receptor activation. J Pharmacol Exp Ther. 2012 Mar;340(3):604-11. doi: 10.1124/jpet.111.189845. Epub 2011 Dec 2. PubMed PMID: 22138372. 9: Abu-Ghefreh AA, Masocha W. Enhancement of antinociception by coadministration of minocycline and a non-steroidal anti-inflammatory drug indomethacin in naïve mice and murine models of LPS-induced thermal hyperalgesia and monoarthritis. BMC Musculoskelet Disord. 2010 Dec 1;11:276. doi: 10.1186/1471-2474-11-276. PubMed PMID: 21122103; PubMed Central PMCID: PMC3009629. 10: Aljofan M, Ding H. High glucose increases expression of cyclooxygenase-2, increases oxidative stress and decreases the generation of nitric oxide in mouse microvessel endothelial cells. J Cell Physiol. 2010 Mar;222(3):669-75. doi: 10.1002/jcp.21986. PubMed PMID: 19950211. 11: Cho Y, Park MJ, Park M, Min SS, Yee J, Kim C, Han MS, Han SH. Effects of CAY10404 on the PKB/Akt and MAPK pathway and apoptosis in non-small cell lung cancer cells. Respirology. 2009 Aug;14(6):850-8. doi: 10.1111/j.1440-1843.2009.01563.x. PubMed PMID: 19703066. 12: Moody TW, Switzer C, Santana-Flores W, Ridnour LA, Berna M, Thill M, Jensen RT, Sparatore A, Del Soldato P, Yeh GC, Roberts DD, Giaccone G, Wink DA. Dithiolethione modified valproate and diclofenac increase E-cadherin expression and decrease proliferation of non-small cell lung cancer cells. Lung Cancer. 2010 May;68(2):154-60. doi: 10.1016/j.lungcan.2009.06.012. Epub 2009 Jul 23. PubMed PMID: 19628293; PubMed Central PMCID: PMC3835159. 13: Rastogi P, Young DM, McHowat J. Tryptase activates calcium-independent phospholipase A2 and releases PGE2 in airway epithelial cells. Am J Physiol Lung Cell Mol Physiol. 2008 Nov;295(5):L925-32. doi: 10.1152/ajplung.90230.2008. Epub 2008 Sep 12. PubMed PMID: 18790994; PubMed Central PMCID: PMC2584891. 14: Hoshino T, Tabuchi K, Hirose Y, Uemaetomari I, Murashita H, Tobita T, Hara A. The non-steroidal anti-inflammatory drugs protect mouse cochlea against acoustic injury. Tohoku J Exp Med. 2008 Sep;216(1):53-9. PubMed PMID: 18719338. 15: Rajagopalan G, Asmann YW, Lytle AK, Tilahun AY, Theuer JE, Smart MK, Patel R, David CS. Cyclooxygenase 2 pathway and its therapeutic inhibition in superantigen-induced toxic shock. Shock. 2008 Dec;30(6):721-8. doi: 10.1097/SHK.0b013e31817048f7. PubMed PMID: 18496243. 16: Tajima T, Murata T, Aritake K, Urade Y, Hirai H, Nakamura M, Ozaki H, Hori M. Lipopolysaccharide induces macrophage migration via prostaglandin D(2) and prostaglandin E(2). J Pharmacol Exp Ther. 2008 Aug;326(2):493-501. doi: 10.1124/jpet.108.137992. Epub 2008 May 20. PubMed PMID: 18492946. 17: Cusimano A, Foderà D, D'Alessandro N, Lampiasi N, Azzolina A, Montalto G, Cervello M. Potentiation of the antitumor effects of both selective cyclooxygenase-1 and cyclooxygenase-2 inhibitors in human hepatic cancer cells by inhibition of the MEK/ERK pathway. Cancer Biol Ther. 2007 Sep;6(9):1461-8. Epub 2007 Jun 26. PubMed PMID: 18424914. 18: Riondino S, Trifirò E, Principessa L, Mascioletti S, Di Renzo L, Gaudio C, Biasucci LM, Crea F, Pulcinelli FM. Lack of biological relevance of platelet cyclooxygenase-2 dependent thromboxane A2 production. Thromb Res. 2008;122(3):359-65. doi: 10.1016/j.thromres.2007.12.011. Epub 2008 Mar 4. PubMed PMID: 18295304. 19: 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. Epub 2007 Aug 1. PubMed PMID: 17668203. 20: Cao J, Kitazawa T, Takehana K, Taneike T. Endogenous prostaglandins regulate spontaneous contractile activity of uterine strips isolated from non-pregnant pigs. Prostaglandins Other Lipid Mediat. 2006 Dec;81(3-4):93-105. Epub 2006 Sep 25. PubMed PMID: 17085318.