Vercirnon

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

MedKoo CAT#: 319723

CAS#: 698394-73-9

Description: Vercirnon, also known as CCX282-B and GSK1605786, is a potent and orally active CCR9 antagonist, which is currently under development for Crohn's disease. CCX282-B inhibited CCR9-mediated Ca(2+) mobilization and chemotaxis on Molt-4 cells with IC(50) values of 5.4 and 3.4 nM, respectively. CCX282-B inhibited CCR9-mediated chemotaxis with an IC(50) of 33 nM. CCX282-B inhibited chemotaxis of primary CCR9-expressing cells to CCL25 with an IC(50) of 6.8 nM. CCX282-B was an equipotent inhibitor of CCL25-directed chemotaxis of both splice forms of CCR9 (CCR9A and CCR9B) with IC(50) values of 2.8 and 2.6 nM, respectively. CCX282-B also inhibited mouse and rat CCR9-mediated chemotaxis.

Chemical Structure

Vercirnon

CAS# 698394-73-9

Instruction

Theoretical Analysis

MedKoo Cat#: 319723
Name: Vercirnon
CAS#: 698394-73-9
Chemical Formula: C22H21ClN2O4S
Exact Mass: 444.09
Molecular Weight: 444.930
Elemental Analysis: C, 59.39; H, 4.76; Cl, 7.97; N, 6.30; O, 14.38; S, 7.21

Price and Availability

Size	Price	Availability	Quantity
1g	USD -1
2g	USD -1
5g	USD -1
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: GSK1605786; GSK 1605786; GSK-1605786; CCX282B; CCX 282B; CCX-282b; CCX282-B; Vercirnon.

IUPAC/Chemical Name: 4-(2-((4-(tert-butyl)phenyl)sulfonamido)-5-chlorobenzoyl)pyridine 1-oxide

InChi Key: JRWROCIMSDXGOZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H21ClN2O4S/c1-22(2,3)16-4-7-18(8-5-16)30(28,29)24-20-9-6-17(23)14-19(20)21(26)15-10-12-25(27)13-11-15/h4-14,24H,1-3H3

SMILES Code: O=C(C1=CC=[N+]([O-])C=C1)C2=CC(Cl)=CC=C2NS(=O)(C3=CC=C(C(C)(C)C)C=C3)=O

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: Related CAS# CAS No. 698394-73-9(Vercirnon) 886214-18-2(Vercirnon Sodium) CCR9 antagonism is a promising new therapeutic approach for the treatment of Crohn's disease. CCR9 is expressed on the cell surface of memory/effector CD4(+) T cells and selectively binds to the small intestinal lymphocyte chemoattractant CCL25 (TECK). Blockade of the CCR9/CCL25 interaction inhibits lymphocyte homing to the intestinal mucosa, thereby limiting inflammation and disease at this site.

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 444.93 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:

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1: Feagan BG, Sandborn WJ, D'Haens G, Lee SD, Allez M, Fedorak RN, Seidler U, Vermeire S, Lawrance IC, Maroney AC, Jurgensen CH, Heath A, Chang DJ. Randomised clinical trial: vercirnon, an oral CCR9 antagonist, vs. placebo as induction therapy in active Crohn's disease. Aliment Pharmacol Ther. 2015 Nov;42(10):1170-81. doi: 10.1111/apt.13398. Epub 2015 Sep 23. PubMed PMID: 26400458.

2: Zhang J, Romero J, Chan A, Goss J, Stucka S, Cross J, Chamberlain B, Varoglu M, Chandonnet H, Ryan D, Lippa B. Biarylsulfonamide CCR9 inhibitors for inflammatory bowel disease. Bioorg Med Chem Lett. 2015 Sep 1;25(17):3661-4. doi: 10.1016/j.bmcl.2015.06.046. Epub 2015 Jun 18. PubMed PMID: 26117562.

3: Löwenberg M, D'Haens G. Next-Generation Therapeutics for IBD. Curr Gastroenterol Rep. 2015 Jun;17(6):21. doi: 10.1007/s11894-015-0444-2. Review. PubMed PMID: 26031830; PubMed Central PMCID: PMC4451973.

4: Wendt E, Keshav S. CCR9 antagonism: potential in the treatment of Inflammatory Bowel Disease. Clin Exp Gastroenterol. 2015 Apr 7;8:119-30. doi: 10.2147/CEG.S48305. eCollection 2015. Review. PubMed PMID: 25897254; PubMed Central PMCID: PMC4396201.

5: Westphal MV, Wolfstädter BT, Plancher JM, Gatfield J, Carreira EM. Evaluation of tert-butyl isosteres: case studies of physicochemical and pharmacokinetic properties, efficacies, and activities. ChemMedChem. 2015 Mar;10(3):461-9. doi: 10.1002/cmdc.201402502. Epub 2015 Jan 28. PubMed PMID: 25630804.

6: Danese S, Panés J. Development of drugs to target interactions between leukocytes and endothelial cells and treatment algorithms for inflammatory bowel diseases. Gastroenterology. 2014 Nov;147(5):981-9. doi: 10.1053/j.gastro.2014.08.044. Epub 2014 Sep 16. Review. PubMed PMID: 25220794.

7: Saruta M, Papadakis KA. Lymphocyte homing antagonists in the treatment of inflammatory bowel diseases. Gastroenterol Clin North Am. 2014 Sep;43(3):581-601. doi: 10.1016/j.gtc.2014.05.012. Epub 2014 Jun 25. Review. PubMed PMID: 25110260.

8: Leiman DA, Lichtenstein GR. Therapy of inflammatory bowel disease: what to expect in the next decade. Curr Opin Gastroenterol. 2014 Jul;30(4):385-90. doi: 10.1097/MOG.0000000000000077. Review. PubMed PMID: 24902037.

9: Lobatón T, Vermeire S, Van Assche G, Rutgeerts P. Review article: anti-adhesion therapies for inflammatory bowel disease. Aliment Pharmacol Ther. 2014 Mar;39(6):579-94. doi: 10.1111/apt.12639. Epub 2014 Jan 30. Review. PubMed PMID: 24479980.

10: Haberer LJ, McSherry I, Cargill A, McCarthy L. Effects of vercirnon on the activity of CYP3A4, CYP2C19 and CYP2C8 enzymes and BCRP and OATP1B1 transporters using probe substrates. Eur J Clin Pharmacol. 2014 Jan;70(1):37-45. doi: 10.1007/s00228-013-1592-7. Epub 2013 Oct 8. PubMed PMID: 24100471; PubMed Central PMCID: PMC3889518.

11: Arseneau KO, Cominelli F. Vercirnon for the treatment of Crohn's disease. Expert Opin Investig Drugs. 2013 Jul;22(7):907-13. doi: 10.1517/13543784.2013.795946. Epub 2013 Apr 30. Review. PubMed PMID: 23627683.

12: Keshav S, Vaňásek T, Niv Y, Petryka R, Howaldt S, Bafutto M, Rácz I, Hetzel D, Nielsen OH, Vermeire S, Reinisch W, Karlén P, Schreiber S, Schall TJ, Bekker P; Prospective Randomized Oral-Therapy Evaluation in Crohn’s Disease Trial-1 PROTECT-1 Study Group. A randomized controlled trial of the efficacy and safety of CCX282-B, an orally-administered blocker of chemokine receptor CCR9, for patients with Crohn's disease. PLoS One. 2013;8(3):e60094. doi: 10.1371/journal.pone.0060094. Epub 2013 Mar 20. PubMed PMID: 23527300; PubMed Central PMCID: PMC3603920.

13: Ghosh N, Chaki R, Mandal SC. Inhibition of selective adhesion molecules in treatment of inflammatory bowel disease. Int Rev Immunol. 2012 Oct;31(5):410-27. doi: 10.3109/08830185.2012.690794. PubMed PMID: 23083349.

14: Thomas S, Baumgart DC. Targeting leukocyte migration and adhesion in Crohn's disease and ulcerative colitis. Inflammopharmacology. 2012 Feb;20(1):1-18. doi: 10.1007/s10787-011-0104-6. Epub 2011 Dec 20. Review. PubMed PMID: 22205271.

15: Walters MJ, Wang Y, Lai N, Baumgart T, Zhao BN, Dairaghi DJ, Bekker P, Ertl LS, Penfold ME, Jaen JC, Keshav S, Wendt E, Pennell A, Ungashe S, Wei Z, Wright JJ, Schall TJ. Characterization of CCX282-B, an orally bioavailable antagonist of the CCR9 chemokine receptor, for treatment of inflammatory bowel disease. J Pharmacol Exp Ther. 2010 Oct;335(1):61-9. doi: 10.1124/jpet.110.169714. Epub 2010 Jul 21. PubMed PMID: 20660125.

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