NBI-74330
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MedKoo CAT#: 206469

CAS#: 855527-92-3 (R-isomer)

Description: NBI-74330 is an antagonist of CXC chemokine receptor 3 (CXCR3) with IC50 values of 7nM to18nM. NBI-74330 attenuates atherosclerotic plaque formation in LDL receptor-deficient mice. Chemokine receptor CXCR3 promotes growth of glioma. CXCR3 antagonism exerts a direct anti-glioma effect and this receptor may be a potential therapeutic target for treating human GBM.


Price and Availability

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5mg USD 150 Inquiry
10mg USD 250 Inquiry
25mg USD 450 Inquiry
50mg USD 850 Inquiry
100mg USD 1350 Inquiry
200mg USD 1950 Inquiry
500mg USD 2650 Inquiry
1g USD 3450 Inquiry
2g USD 6450 Inquiry
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Pricing updated 2020-02-17. Prices are subject to change without notice.

NBI-74330, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206469
Name: NBI-74330
CAS#: 855527-92-3 (R-isomer)
Chemical Formula: C32H27F4N5O3
Exact Mass: 605.205
Molecular Weight: 605.59
Elemental Analysis: C, 63.47; H, 4.49; F, 12.55; N, 11.56; O, 7.93


Related CAS #: 473722-68-8 (racemate)   855527-92-3 (R-isomer)    

Synonym: NBI-74330; NBI 74330; NBI74330.

IUPAC/Chemical Name: N-[(1R)-1-[3-(4-Ethoxyphenyl)-3,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-4-fluoro-N-(3-pyridinylmethyl)-3-(trifluoromethyl)benzeneacetamide

InChi Key: XMRGQUDUVGRCBS-HXUWFJFHSA-N

InChi Code: InChI=1S/C32H27F4N5O3/c1-3-44-24-11-9-23(10-12-24)41-30(39-29-25(31(41)43)7-5-15-38-29)20(2)40(19-22-6-4-14-37-18-22)28(42)17-21-8-13-27(33)26(16-21)32(34,35)36/h4-16,18,20H,3,17,19H2,1-2H3/t20-/m1/s1

SMILES Code: O=C(N([[email protected]@H](C1=NC2=NC=CC=C2C(N1C3=CC=C(OCC)C=C3)=O)C)CC4=CC=CN=C4)CC5=CC=C(F)C(C(F)(F)F)=C5


Technical Data

Appearance:
Solid powder

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
2934.99.90.01


References

1: Scholten DJ, Roumen L, Wijtmans M, Verkade-Vreeker MC, Custers H, Lai M, de Hooge D, Canals M, de Esch IJ, Smit MJ, de Graaf C, Leurs R. Identification of overlapping but differential binding sites for the high-affinity CXCR3 antagonists NBI-74330 and VUF11211. Mol Pharmacol. 2014 Jan;85(1):116-26. doi: 10.1124/mol.113.088633. Epub 2013 Oct 30. PubMed PMID: 24174496.

2: Watts AO, Scholten DJ, Heitman LH, Vischer HF, Leurs R. Label-free impedance responses of endogenous and synthetic chemokine receptor CXCR3 agonists correlate with Gi-protein pathway activation. Biochem Biophys Res Commun. 2012 Mar 9;419(2):412-8. doi: 10.1016/j.bbrc.2012.02.036. Epub 2012 Feb 13. PubMed PMID: 22349504.

3: Korniejewska A, McKnight AJ, Johnson Z, Watson ML, Ward SG. Expression and agonist responsiveness of CXCR3 variants in human T lymphocytes. Immunology. 2011 Apr;132(4):503-15. doi: 10.1111/j.1365-2567.2010.03384.x. Epub 2011 Jan 24. PubMed PMID: 21255008; PubMed Central PMCID: PMC3075504.

4: Liu C, Luo D, Reynolds BA, Meher G, Katritzky AR, Lu B, Gerard CJ, Bhadha CP, Harrison JK. Chemokine receptor CXCR3 promotes growth of glioma. Carcinogenesis. 2011 Feb;32(2):129-37. doi: 10.1093/carcin/bgq224. Epub 2010 Nov 3. PubMed PMID: 21051441; PubMed Central PMCID: PMC3026840.

5: Kapoor S. Emerging new chemokine CXCR3 antagonists and their potential clinical and therapeutic applications. Hepatology. 2009 Apr;49(4):1400-1. doi: 10.1002/hep.22781. PubMed PMID: 19330874.

6: Verzijl D, Storelli S, Scholten DJ, Bosch L, Reinhart TA, Streblow DN, Tensen CP, Fitzsimons CP, Zaman GJ, Pease JE, de Esch IJ, Smit MJ, Leurs R. Noncompetitive antagonism and inverse agonism as mechanism of action of nonpeptidergic antagonists at primate and rodent CXCR3 chemokine receptors. J Pharmacol Exp Ther. 2008 May;325(2):544-55. doi: 10.1124/jpet.107.134783. Epub 2008 Feb 12. PubMed PMID: 18270317; PubMed Central PMCID: PMC3659174.

7: van Wanrooij EJ, de Jager SC, van Es T, de Vos P, Birch HL, Owen DA, Watson RJ, Biessen EA, Chapman GA, van Berkel TJ, Kuiper J. CXCR3 antagonist NBI-74330 attenuates atherosclerotic plaque formation in LDL receptor-deficient mice. Arterioscler Thromb Vasc Biol. 2008 Feb;28(2):251-7. Epub 2007 Nov 29. PubMed PMID: 18048768.

8: Jopling LA, Watt GF, Fisher S, Birch H, Coggon S, Christie MI. Analysis of the pharmacokinetic/pharmacodynamic relationship of a small molecule CXCR3 antagonist, NBI-74330, using a murine CXCR3 internalization assay. Br J Pharmacol. 2007 Dec;152(8):1260-71. Epub 2007 Nov 5. PubMed PMID: 17982480; PubMed Central PMCID: PMC2190000.

9: Storelli S, Verzijl D, Al-Badie J, Elders N, Bosch L, Timmerman H, Smit MJ, De Esch IJ, Leurs R. Synthesis and structure-activity relationships of 3H-quinazolin-4-ones and 3H-pyrido[2,3-d]pyrimidin-4-ones as CXCR3 receptor antagonists. Arch Pharm (Weinheim). 2007 Jun;340(6):281-91. PubMed PMID: 17562560.

10: Heise CE, Pahuja A, Hudson SC, Mistry MS, Putnam AL, Gross MM, Gottlieb PA, Wade WS, Kiankarimi M, Schwarz D, Crowe P, Zlotnik A, Alleva DG. Pharmacological characterization of CXC chemokine receptor 3 ligands and a small molecule antagonist. J Pharmacol Exp Ther. 2005 Jun;313(3):1263-71. Epub 2005 Mar 10. PubMed PMID: 15761110.