WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H407335
CAS#: 130717-51-0
Description: FR-122047 is a potent and selective cyclooxygenase-1 (COX-1) inhibitor (IC50 values are 0.028 and 65 μM for COX-1 and COX-2 respectively). FR122047 treatment led to a distinct suppression of cell growth in MCF-7 cells. FR122047 may have an anti-cancer potential in breast cancer.
Hodoodo Cat#: H407335
Name: FR-122047 HCl
CAS#: 130717-51-0
Chemical Formula: C23H26ClN3O3S
Exact Mass: 459.14
Molecular Weight: 459.989
Elemental Analysis: C, 60.06; H, 5.70; Cl, 7.71; N, 9.14; O, 10.43; S, 6.97
Synonym: FR-122047; FR 122047; FR122047.
IUPAC/Chemical Name: (4,5-bis(4-methoxyphenyl)thiazol-2-yl)(4-methylpiperazin-1-yl)methanone hydrochloride
InChi Key: YWMAVHIKOAOSFM-UHFFFAOYSA-N
InChi Code: InChI=1S/C23H25N3O3S.ClH/c1-25-12-14-26(15-13-25)23(27)22-24-20(16-4-8-18(28-2)9-5-16)21(30-22)17-6-10-19(29-3)11-7-17;/h4-11H,12-15H2,1-3H3;1H
SMILES Code: CN1CCN(C(C2=NC(C3=CC=C(OC)C=C3)=C(C4=CC=C(OC)C=C4)S2)=O)CC1.[H]Cl
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, not in water
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 459.99 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Sandberg M, Jansson L. Effects of cyclooxygenase inhibition on insulin release and pancreatic islet blood flow in rats. Ups J Med Sci. 2014 Nov;119(4):316-23. doi: 10.3109/03009734.2014.964381. Epub 2014 Oct 7. PubMed PMID: 25291145; PubMed Central PMCID: PMC4248071.
2: Larsson-Callerfelt AK, Dahlén SE, Kühl AR, Lex D, Uhlig S, Martin C. Modulation of antigen-induced responses by serotonin and prostaglandin E2 via EP1 and EP4 receptors in the peripheral rat lung. Eur J Pharmacol. 2013 Jan 15;699(1-3):141-9. doi: 10.1016/j.ejphar.2012.11.039. Epub 2012 Dec 3. PubMed PMID: 23220160.
3: Restrepo B, García M, López C, Martín ML, San Román L, Morán A. The cyclooxygenase and nitric oxide synthesis/pathways mediate the inhibitory serotonergic response to the pressor effect elicited by sympathetic stimulation in long-term diabetic pithed rats. Pharmacology. 2012;90(3-4):169-76. doi: 10.1159/000341911. Epub 2012 Aug 29. PubMed PMID: 22948792.
4: Morales A, Gao W, Lu J, Xing J, Li J. Muscle cyclo-oxygenase-2 pathway contributes to the exaggerated muscle mechanoreflex in rats with congestive heart failure. Exp Physiol. 2012 Aug;97(8):943-54. doi: 10.1113/expphysiol.2012.065425. Epub 2012 Apr 20. PubMed PMID: 22523381; PubMed Central PMCID: PMC3606264.
5: Nam YH, Min A, Kim SH, Lee YA, Kim KA, Song KJ, Shin MH. Leukotriene B(4) receptors BLT1 and BLT2 are involved in interleukin-8 production in human neutrophils induced by Trichomonas vaginalis-derived secretory products. Inflamm
Res. 2012 Feb;61(2):97-102. doi: 10.1007/s00011-011-0425-3. Epub 2012 Jan 4. PubMed PMID: 22215047.
6: Restrepo B, García M, Rodríguez-Barbero A, Román LS, Martin ML, Morán A. Participation of cyclooxygenase pathway in the vasoconstriction induced by 5-HT in the in situ autoperfused kidney of long-term diabetic rats. Eur J Pharmacol. 2011 May 20;659(1):37-44. doi: 10.1016/j.ejphar.2011.03.006. Epub 2011 Mar 22. PubMed PMID: 21414306.
7: Jeong HS, Kim JH, Choi HY, Lee ER, Cho SG. Induction of cell growth arrest and apoptotic cell death in human breast cancer MCF-7 cells by the COX-1 inhibitor FR122047. Oncol Rep. 2010 Aug;24(2):351-6. PubMed PMID: 20596620.
8: Miozza V, Borda E, S-Borda L, Busch L. Increase nitric oxide synthase activity in parotid glands from rats with experimental periodontitis. Oral Dis. 2010 Nov;16(8):801-6. doi: 10.1111/j.1601-0825.2010.01691.x. PubMed PMID: 20561219.
9: Miozza V, Borda E, Sterin-Borda L, Busch L. Experimental periodontitis induces a cAMP-dependent increase in amylase activity in parotid glands from male rats. Inflammation. 2009 Dec;32(6):357-63. doi: 10.1007/s10753-009-9142-2. PubMed PMID: 19669869.
10: Collins C, Klausner AP, Herrick B, Koo HP, Miner AS, Henderson SC, Ratz PH. Potential for control of detrusor smooth muscle spontaneous rhythmic contraction
by cyclooxygenase products released by interstitial cells of Cajal. J Cell Mol Med. 2009 Sep;13(9B):3236-50. doi: 10.1111/j.1582-4934.2009.00714.x. Epub 2009 Feb 20. PubMed PMID: 19243470; PubMed Central PMCID: PMC4516481.
11: Selg E, Låstbom L, Ryrfeldt A, Kumlin M, Dahlén SE. Effects of selective and
non-selective COX inhibitors on antigen-induced release of prostanoid mediators and bronchoconstriction in the isolated perfused and ventilated guinea pig lung.
Prostaglandins Leukot Essent Fatty Acids. 2008 Feb;78(2):89-97. doi: 10.1016/j.plefa.2008.01.001. PubMed PMID: 18294831.
12: Qi W, Wei JX, Dorairaj I, Mahajan RP, Wilson VG. Evidence that a prostanoid produced by cyclo-oxygenase-2 enhances contractile responses of the porcine isolated coronary artery following exposure to lipopolysaccharide. Br J Anaesth.
2007 Mar;98(3):323-30. Epub 2007 Feb 1. PubMed PMID: 17272385.
13: Wibberley A, McCafferty GP, Evans C, Edwards RM, Hieble JP. Dual, but not selective, COX-1 and COX-2 inhibitors, attenuate acetic acid-evoked bladder irritation in the anaesthetised female cat. Br J Pharmacol. 2006 May;148(2):154-61. PubMed PMID: 16547526; PubMed Central PMCID: PMC1617054.
14: Abe T, Hayasaka Y, Zhang XY, Hayasaka S. Effects of intravenous administration of FR122047 (a selective cyclooxygenase 1 inhibitor) and FR188582
(a selective cyclooxygenase 2 inhibitor) on prostaglandin-E2-induced aqueous flare elevation in pigmented rabbits. Ophthalmic Res. 2004 Nov-Dec;36(6):321-6. PubMed PMID: 15627832.
15: Ochi T, Ohkubo Y, Mutoh S. Role of cyclooxygenase-2, but not cyclooxygenase-1, on type II collagen-induced arthritis in DBA/1J mice. Biochem Pharmacol. 2003 Sep 15;66(6):1055-60. PubMed PMID: 12963493.
16: Ochi T, Goto T. Differential effect of FR122047, a selective cyclo-oxygenase-1 inhibitor, in rat chronic models of arthritis. Br J Pharmacol.
2002 Feb;135(3):782-8. PubMed PMID: 11834626; PubMed Central PMCID: PMC1573175.
17: Ochi T, Motoyama Y, Goto T. The analgesic effect profile of FR122047, a selective cyclooxygenase-1 inhibitor, in chemical nociceptive models. Eur J Pharmacol. 2000 Mar 10;391(1-2):49-54. PubMed PMID: 10720634.
18: Tanaka A, Sakai H, Motoyama Y, Ishikawa T, Takasugi H. Antiplatelet agents based on cyclooxygenase inhibition without ulcerogenesis. Evaluation and synthesis of 4,5-bis(4-methoxyphenyl)-2-substituted-thiazoles. J Med Chem. 1994 Apr 15;37(8):1189-99. PubMed PMID: 8164261.
19: Dohi M, Sakata Y, Seki J, Namikawa Y, Fujisaki J, Tanaka A, Takasugi H, Motoyama Y, Yoshida K. The anti-platelet actions of FR122047, a novel cyclooxygenase inhibitor. Eur J Pharmacol. 1993 Oct 19;243(2):179-84. PubMed PMID: 8276067.
