Navarixin
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MedKoo CAT#: 206586

CAS#: 473727-83-2

Description: Navarixin, also known as SCH527123, PS291822 and MK-7123, is a potent CXCR2 antagonist. SCH-527123 shows antitumor activity and sensitizes cells to oxaliplatin in preclinical colon cancer models. SCH-527123 showed concentration-dependent antiproliferative effects in HCT116, Caco2, and their respective IL-8-overexpressing variants colorectal cancer cell lines. CH-527123 was able to suppress CXCR2-mediated signal transduction as shown through decreased phosphorylation of the NF-κB/mitogen-activated protein kinase (MAPK)/AKT pathway. SCH-527123 treatment decreased tumor growth and microvessel density when compared with vehicle-treated tumors.


Price and Availability

Size Price Shipping out time Quantity
10mg USD 150 Same Day
25mg USD 250 Same Day
50mg USD 450 Same Day
100mg USD 750 Same Day
200mg USD 1350 Same Day
500mg USD 2150 Same Day
1g USD 3650 Same Day
2g USD 6450 Same Day
Inquire bulk and customized quantity

Pricing updated 2020-09-22. Prices are subject to change without notice.

Navarixin, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 5g may be 6 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206586
Name: Navarixin
CAS#: 473727-83-2
Chemical Formula: C21H23N3O5
Exact Mass: 397.1638
Molecular Weight: 397.431
Elemental Analysis: C, 63.47; H, 5.83; N, 10.57; O, 20.13


Related CAS #: 862464-58-2 (hydrate)   473727-83-2    

Synonym: SCH527123; SCH-527123; SCH 527123; MK-7123; MK7123; MK 7123; PS291822; PS-291822; PS 291822; Navarixin monohydrate; Navarixin

IUPAC/Chemical Name: (R)-2-hydroxy-N,N-dimethyl-3-((2-((1-(5-methylfuran-2-yl)propyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)benzamide

InChi Key: IXBYSXNOKFHHDR-QGZVFWFLSA-N

InChi Code: 1S/C23H26N2O5/c1-5-7-17(18-11-10-13(2)30-18)24-19-16(21(27)22(19)28)12-14-8-6-9-15(20(14)26)23(29)25(3)4/h6,8-11,17,24,26H,5,7,12H2,1-4H3/t17-/m1/s1

SMILES Code: O=C(N(C)C)C1=CC=CC(NC2=C(N[C@@H](C3=CC=C(C)O3)CC)C(C2=O)=O)=C1O


Technical Data

Appearance:
White to off-white solid powder

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

Certificate of Analysis:

Safety Data Sheet (SDS):

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 (>40mg/mL)

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


References

1: Mladic M, Scholten DJ, Niessen WM, Somsen GW, Smit MJ, Kool J. At-line coupling of LC-MS to bioaffinity and selectivity assessment for metabolic profiling of ligands towards chemokine receptors CXCR1 and CXCR2. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:42-53. doi: 10.1016/j.jchromb.2015.08.004. Epub 2015 Aug 10. PubMed PMID: 26301479.

2: Rennard SI, Dale DC, Donohue JF, Kanniess F, Magnussen H, Sutherland ER, Watz H, Lu S, Stryszak P, Rosenberg E, Staudinger H. CXCR2 Antagonist MK-7123. A Phase 2 Proof-of-Concept Trial for Chronic Obstructive Pulmonary Disease. Am J Respir Crit Care Med. 2015 May 1;191(9):1001-11. doi: 10.1164/rccm.201405-0992OC. PubMed PMID: 25695403.

3: Hastrup N, Khalilieh S, Dale DC, Hanson LG, Magnusson P, Tzontcheva A, Tseng J, Huyck S, Rosenberg E, Krogsgaard K. The effects of the CXCR2 antagonist, MK-7123, on bone marrow functions in healthy subjects. Cytokine. 2015 Apr;72(2):197-203. doi: 10.1016/j.cyto.2015.01.002. Epub 2015 Feb 4. PubMed PMID: 25661195.

4: Russo RC, Garcia CC, Teixeira MM, Amaral FA. The CXCL8/IL-8 chemokine family and its receptors in inflammatory diseases. Expert Rev Clin Immunol. 2014 May;10(5):593-619. doi: 10.1586/1744666X.2014.894886. Epub 2014 Mar 29. PubMed PMID: 24678812.

5: Kredel S, Wolff M, Gierschik P, Heilker R. Phenotypic analysis of chemokine-driven actin reorganization in primary human neutrophils. Assay Drug Dev Technol. 2014 Mar;12(2):120-8. doi: 10.1089/adt.2013.553. Epub 2014 Feb 28. PubMed PMID: 24579814.

6: Yaqub F. 2013 American Thoracic Society International Conference. Lancet Respir Med. 2013 Jul;1(5):359. doi: 10.1016/S2213-2600(13)70080-8. Epub 2013 May 31. PubMed PMID: 24429194.

7: Seiberling M, Kamtchoua T, Stryszak P, Ma X, Langdon RB, Khalilieh S. Humoral immunity and delayed-type hypersensitivity in healthy subjects treated for 30 days with MK-7123, a selective CXCR2 antagonist. Int Immunopharmacol. 2013 Oct;17(2):178-83. doi: 10.1016/j.intimp.2013.05.029. Epub 2013 Jun 19. PubMed PMID: 23791619.

8: Nair P, Gaga M, Zervas E, Alagha K, Hargreave FE, O'Byrne PM, Stryszak P, Gann L, Sadeh J, Chanez P; Study Investigators. Safety and efficacy of a CXCR2 antagonist in patients with severe asthma and sputum neutrophils: a randomized, placebo-controlled clinical trial. Clin Exp Allergy. 2012 Jul;42(7):1097-103. doi: 10.1111/j.1365-2222.2012.04014.x. PubMed PMID: 22702508.

9: Aul R, Patel S, Summerhill S, Kilty I, Plumb J, Singh D. LPS challenge in healthy subjects: an investigation of neutrophil chemotaxis mechanisms involving CXCR1 and CXCR2. Int Immunopharmacol. 2012 Jul;13(3):225-31. doi: 10.1016/j.intimp.2012.04.008. Epub 2012 May 2. PubMed PMID: 22561413.

10: Ning Y, Labonte MJ, Zhang W, Bohanes PO, Gerger A, Yang D, Benhaim L, Paez D, Rosenberg DO, Nagulapalli Venkata KC, Louie SG, Petasis NA, Ladner RD, Lenz HJ. The CXCR2 antagonist, SCH-527123, shows antitumor activity and sensitizes cells to oxaliplatin in preclinical colon cancer models. Mol Cancer Ther. 2012 Jun;11(6):1353-64. doi: 10.1158/1535-7163.MCT-11-0915. Epub 2012 Mar 5. PubMed PMID: 22391039.

11: Burton VJ, Holmes AM, Ciuclan LI, Robinson A, Roger JS, Jarai G, Pearce AC, Budd DC. Attenuation of leukocyte recruitment via CXCR1/2 inhibition stops the progression of PAH in mice with genetic ablation of endothelial BMPR-II. Blood. 2011 Oct 27;118(17):4750-8. doi: 10.1182/blood-2011-05-347393. Epub 2011 Sep 7. PubMed PMID: 21900197; PubMed Central PMCID: PMC3208288.

12: Varney ML, Singh S, Li A, Mayer-Ezell R, Bond R, Singh RK. Small molecule antagonists for CXCR2 and CXCR1 inhibit human colon cancer liver metastases. Cancer Lett. 2011 Jan 28;300(2):180-8. doi: 10.1016/j.canlet.2010.10.004. Epub 2010 Oct 29. PubMed PMID: 21035946; PubMed Central PMCID: PMC2994987.

13: Salchow K, Bond ME, Evans SC, Press NJ, Charlton SJ, Hunt PA, Bradley ME. A common intracellular allosteric binding site for antagonists of the CXCR2 receptor. Br J Pharmacol. 2010 Apr;159(7):1429-39. doi: 10.1111/j.1476-5381.2009.00623.x. Epub 2010 Mar 3. PubMed PMID: 20233217; PubMed Central PMCID: PMC2850400.

14: Gernez Y, Tirouvanziam R, Chanez P. Neutrophils in chronic inflammatory airway diseases: can we target them and how? Eur Respir J. 2010 Mar;35(3):467-9. doi: 10.1183/09031936.00186109. PubMed PMID: 20190324.

15: Kredel S, Wolff M, Wiedenmann J, Moepps B, Nienhaus GU, Gierschik P, Kistler B, Heilker R. CXCR2 inverse agonism detected by arrestin redistribution. J Biomol Screen. 2009 Oct;14(9):1076-91. doi: 10.1177/1087057109344616. Epub 2009 Sep 22. PubMed PMID: 19773589.

16: Holz O, Khalilieh S, Ludwig-Sengpiel A, Watz H, Stryszak P, Soni P, Tsai M, Sadeh J, Magnussen H. SCH527123, a novel CXCR2 antagonist, inhibits ozone-induced neutrophilia in healthy subjects. Eur Respir J. 2010 Mar;35(3):564-70. doi: 10.1183/09031936.00048509. Epub 2009 Jul 30. PubMed PMID: 19643947.

17: Singh S, Sadanandam A, Nannuru KC, Varney ML, Mayer-Ezell R, Bond R, Singh RK. Small-molecule antagonists for CXCR2 and CXCR1 inhibit human melanoma growth by decreasing tumor cell proliferation, survival, and angiogenesis. Clin Cancer Res. 2009 Apr 1;15(7):2380-6. doi: 10.1158/1078-0432.CCR-08-2387. Epub 2009 Mar 17. PubMed PMID: 19293256; PubMed Central PMCID: PMC4232212.

18: Gonsiorek W, Fan X, Hesk D, Fossetta J, Qiu H, Jakway J, Billah M, Dwyer M, Chao J, Deno G, Taveras A, Lundell DJ, Hipkin RW. Pharmacological characterization of Sch527123, a potent allosteric CXCR1/CXCR2 antagonist. J Pharmacol Exp Ther. 2007 Aug;322(2):477-85. Epub 2007 May 11. PubMed PMID: 17496166.

19: Chapman RW, Minnicozzi M, Celly CS, Phillips JE, Kung TT, Hipkin RW, Fan X, Rindgen D, Deno G, Bond R, Gonsiorek W, Billah MM, Fine JS, Hey JA. A novel, orally active CXCR1/2 receptor antagonist, Sch527123, inhibits neutrophil recruitment, mucus production, and goblet cell hyperplasia in animal models of pulmonary inflammation. J Pharmacol Exp Ther. 2007 Aug;322(2):486-93. Epub 2007 May 11. PubMed PMID: 17496165.

20: Dwyer MP, Yu Y, Chao J, Aki C, Chao J, Biju P, Girijavallabhan V, Rindgen D, Bond R, Mayer-Ezel R, Jakway J, Hipkin RW, Fossetta J, Gonsiorek W, Bian H, Fan X, Terminelli C, Fine J, Lundell D, Merritt JR, Rokosz LL, Kaiser B, Li G, Wang W, Stauffer T, Ozgur L, Baldwin J, Taveras AG. Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5- methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123): a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist. J Med Chem. 2006 Dec 28;49(26):7603-6. PubMed PMID: 17181143.