Bepafant
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MedKoo CAT#: 528324

CAS#: 114776-28-2

Description: Bepafant, also known as WEB-2170 and STY-2108, is a platelet activating factor (PAF) antagonist potentially for the treatment of asthma. Bepafant triggered apoptosis in NB4, KG1, and NB4-MR4 cells where PTEN was expressed, but not in THP1 and U937 cells where PTEN was absent. Bepafant may produce significant anti-inflammatory effects.


Price and Availability

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Price

5mg
USD 330
Size
Price

Size
Price

Bepafant (WEB-2170, STY-2108) purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 528324
Name: Bepafant
CAS#: 114776-28-2
Chemical Formula: C23H22ClN5O2S
Exact Mass: 467.1183
Molecular Weight: 467.972
Elemental Analysis: C, 59.03; H, 4.74; Cl, 7.58; N, 14.97; O, 6.84; S, 6.85


Related CAS #: 114776-47-5  

Synonym: Bepafant; WEB-2170; WEB 2170; WEB2170; STY-2108; STY 2108; STY2108

IUPAC/Chemical Name: (6-(2-chlorophenyl)-1-methyl-8,9-dihydro-4H,7H-cyclopenta[4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-8-yl)(morpholino)methanone

InChi Key: FWYVRZOREBYLCY-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H22ClN5O2S/c1-13-26-27-19-12-25-21(15-4-2-3-5-17(15)24)20-16-10-14(11-18(16)32-23(20)29(13)19)22(30)28-6-8-31-9-7-28/h2-5,14H,6-12H2,1H3

SMILES Code: O=C(N1CCOCC1)C2CC(S3)=C(C4=C3N5C(CN=C4C6=CC=CC=C6Cl)=NN=C5C)C2


Technical Data

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).

Harmonized System Code:
293490


References

1: Correa-Costa M, Andrade-Oliveira V, Braga TT, Castoldi A, Aguiar CF, Origassa CS, Rodas AC, Hiyane MI, Malheiros DM, Rios FJ, Jancar S, Câmara NO. Activation of platelet-activating factor receptor exacerbates renal inflammation and promotes fibrosis. Lab Invest. 2014 Apr;94(4):455-66. doi: 10.1038/labinvest.2013.155. PubMed PMID: 24492283.

2: Tsoupras AB, Papakyriakou A, Demopoulos CA, Philippopoulos AI. Synthesis, biochemical evaluation and molecular modeling studies of novel rhodium complexes with nanomolar activity against Platelet Activating Factor. J Inorg Biochem. 2013 Mar;120:63-73. doi: 10.1016/j.jinorgbio.2012.12.004. PubMed PMID: 23318288.

3: Bae R, Arteaga A, Raj JU, Ibe BO. Albuterol isomers modulate platelet-activating factor synthesis and receptor signaling in human bronchial smooth muscle cells. Int Arch Allergy Immunol. 2012;158(1):18-26. doi: 10.1159/000330029. PubMed PMID: 22212397.

4: Howard KM, Abdel-Al M, Ditmyer M, Patel N. Lipopolysaccharide and platelet-activating factor stimulate expression of platelet-activating factor acetylhydrolase via distinct signaling pathways. Inflamm Res. 2011 Aug;60(8):735-44. doi: 10.1007/s00011-011-0326-5. PubMed PMID: 21432021; PubMed Central PMCID: PMC3134448.

5: de Oliveira SI, Andrade LN, Onuchic AC, Nonogaki S, Fernandes PD, Pinheiro MC, Rohde CB, Chammas R, Jancar S. Platelet-activating factor receptor (PAF-R)-dependent pathways control tumour growth and tumour response to chemotherapy. BMC Cancer. 2010 May 13;10:200. doi: 10.1186/1471-2407-10-200. PubMed PMID: 20465821; PubMed Central PMCID: PMC2881890.

6: Cellai C, Laurenzana A, Bianchi E, Sdelci S, Manfredini R, Vannucchi AM, Caporale R, Balliu M, Mannelli F, Ferrari S, Bosi A, Miniati D, Cocco PL, Veronneau S, Stankova J, Paoletti F. Mechanistic insight into WEB-2170-induced apoptosis in human acute myelogenous leukemia cells: the crucial role of PTEN. Exp Hematol. 2009 Oct;37(10):1176-1185.e21. doi: 10.1016/j.exphem.2009.07.002. PubMed PMID: 19615424.

7: Chen C, Xia SH, Chen H, Li XH. Therapy for acute pancreatitis with platelet-activating factor receptor antagonists. World J Gastroenterol. 2008 Aug 14;14(30):4735-8. Review. PubMed PMID: 18720532; PubMed Central PMCID: PMC2739333.

8: Ibe BO, Abdallah MF, Portugal AM, Raj JU. Platelet-activating factor stimulates ovine foetal pulmonary vascular smooth muscle cell proliferation: role of nuclear factor-kappa B and cyclin-dependent kinases. Cell Prolif. 2008 Apr;41(2):208-29. doi: 10.1111/j.1365-2184.2008.00517.x. PubMed PMID: 18336468.

9: Landgraf RG, Nossi DF, Sirois P, Jancar S. Prostaglandins, leukotrienes and PAF selectively modulate lymphocyte subset and eosinophil infiltration into the airways in a murine model of asthma. Prostaglandins Leukot Essent Fatty Acids. 2007 Oct-Nov;77(3-4):163-72. PubMed PMID: 17923399.

10: Souza LJ, Shio MT, Molan NA, Machado MC, Jancar S. Acute pancreatitis affects non-parenchymal liver cells by a mechanism dependent on platelet-activating factor. Pancreatology. 2007;7(1):67-73. PubMed PMID: 17449968.

11: Riccio M, Pangrazi PP, Campodonico A, Scalise A, Marchesini A, Talevi D, Carboni A, Bertani C, Bertani A, Mazzanti L. Combined use of WEB2170 and HBO therapy can reduce ischemia and reperfusion injury to the skeletal muscle in a rabbit model. Microsurgery. 2007;27(1):43-7. PubMed PMID: 17206621.

12: Kassuya CA, Silvestre A, Menezes-de-Lima O Jr, Marotta DM, Rehder VL, Calixto JB. Antiinflammatory and antiallodynic actions of the lignan niranthin isolated from Phyllanthus amarus. Evidence for interaction with platelet activating factor receptor. Eur J Pharmacol. 2006 Sep 28;546(1-3):182-8. PubMed PMID: 16925995.

13: de Oliveira SI, Fernandes PD, Amarante Mendes JG, Jancar S. Phagocytosis of apoptotic and necrotic thymocytes is inhibited by PAF-receptor antagonists and affects LPS-induced COX-2 expression in murine macrophages. Prostaglandins Other Lipid Mediat. 2006 Jul;80(1-2):62-73. PubMed PMID: 16846787.

14: De Plaen IG, Han XB, Liu X, Hsueh W, Ghosh S, May MJ. Lipopolysaccharide induces CXCL2/macrophage inflammatory protein-2 gene expression in enterocytes via NF-kappaB activation: independence from endogenous TNF-alpha and platelet-activating factor. Immunology. 2006 Jun;118(2):153-63. PubMed PMID: 16771850; PubMed Central PMCID: PMC1782278.

15: Jawień J, Lomnicka M, Korbut R, Chłopicki S. The involvement of adhesion molecules and lipid mediators in the adhesion of human platelets to eosinophils. J Physiol Pharmacol. 2005 Dec;56(4):637-48. PubMed PMID: 16391420.

16: Laurenzana A, Cellai C, Vannucchi AM, Pancrazzi A, Romanelli MN, Paoletti F. WEB-2086 and WEB-2170 trigger apoptosis in both ATRA-sensitive and -resistant promyelocytic leukemia cells and greatly enhance ATRA differentiation potential. Leukemia. 2005 Mar;19(3):390-5. PubMed PMID: 15674364.

17: Penna C, Alloatti G, Cappello S, Gattullo D, Berta G, Mognetti B, Losano G, Pagliaro P. Platelet-activating factor induces cardioprotection in isolated rat heart akin to ischemic preconditioning: role of phosphoinositide 3-kinase and protein kinase C activation. Am J Physiol Heart Circ Physiol. 2005 May;288(5):H2512-20. PubMed PMID: 15637120.

18: Karasen RM, Uslu C, Gundogdu C, Taysi S, Akcay F. Effect of WEB 2170 BS, platelet activating factor receptor inhibitor, in the rabbit model of sinusitis. Ann Otol Rhinol Laryngol. 2004 Jun;113(6):477-82. PubMed PMID: 15224833.

19: Jakubowski A, Olszanecki R, Chlopicki S. Involvement of platelet activating factor in immediate heart response to lipopolysaccharide. J Physiol Pharmacol. 2004 Jun;55(2):409-21. PubMed PMID: 15213362.

20: Jung TT, John EO, Park SK, Park YS, Rhee CK. Effect of platelet activating factor with and without receptor antagonist (WEB2170) on morphology of isolated cochlear outer hair cells. Ann Otol Rhinol Laryngol. 2004 Feb;113(2):164-8. PubMed PMID: 14994775.