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SML0238

Sigma-Aldrich

WEB2086

≥98% (HPLC)

Synonym(s):

3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]-1-(4-morpholinyl)-1-propanone, Apafant, WEB 2086BS

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About This Item

Empirical Formula (Hill Notation):
C22H22ClN5O2S
CAS Number:
105219-56-5
Molecular Weight:
455.96
MDL number:
MFCD00865271
UNSPSC Code:
12352200
PubChem Substance ID:
329825250
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 10 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

Cc1nnc2CN=C(c3ccccc3Cl)c4cc(CCC(=O)N5CCOCC5)sc4-n12

InChI

1S/C22H22ClN5O2S/c1-14-25-26-19-13-24-21(16-4-2-3-5-18(16)23)17-12-15(31-22(17)28(14)19)6-7-20(29)27-8-10-30-11-9-27/h2-5,12H,6-11,13H2,1H3

InChI key

JGPJQFOROWSRRS-UHFFFAOYSA-N

Biochem/physiol Actions

WEB 2086 inhibits PAF mediated chemotaxis and leukotriene C4 production in eosinophils. It prevents surge in airway resistance and cardiovascular side effects mediated by PAF inhalation.
WEB2086 is a very potent, selective platelet-activating factor (PAF) antagonist (IC50 = 16 nM). WEB2086 inhibits the proliferation of tumor cells and slows tumor growth in xenograft tumor models, and has been shown to inhibit angiogenesis.

Features and Benefits

This compound is featured on the PAF Receptor page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yoichi Ajiro et al.
American journal of physiology. Heart and circulatory physiology, 301(6), H2395-H2401 (2011-09-29)
Sodium-hydrogen exchanger (NHE), the principal sarcolemmal acid extruder in ventricular myocytes, is stimulated by a variety of autocrine/paracrine factors and contributes to myocardial injury and arrhythmias during ischemia-reperfusion. Platelet-activating factor (PAF; 1-o-alkyl-2-acetyl-sn-glycero-3-phosphocholine) is a potent proinflammatory phospholipid that is released
The effect of WEB 2086 on PAF-induced eosinophil chemotaxis and LTC 4 production from eosinophils
Miyagawa H, et al.
Agents and Actions, 37(1-2), 39-43 (1992)
Anita Thyagarajan et al.
International journal of molecular sciences, 20(1) (2018-12-24)
Studies, including ours, have shown that pro-oxidative stressors, such as chemotherapeutic agents, generate oxidized lipids with agonistic platelet-activating factor (PAF) activity. Importantly, recent reports have implicated that these PAF-agonists are transported extracellularly via microvesicle particles (MVPs). While the role of
Izumi Kikuchi et al.
American journal of respiratory cell and molecular biology, 34(6), 760-765 (2006-02-04)
Neutrophilic inflammation observed with severe asthma is often associated with interleukin-8 (IL-8). Neutrophils can secrete a variety of mediators that may augment the migration of eosinophils. We have reported a positive correlation between the concentrations of neutrophils and eosinophils in
Julie S Lefebvre et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 24(2), 637-647 (2009-10-22)
Activation of toll-like receptors (TLRs) and polymorphonuclear leukocyte (PMN) accumulation at infection sites are critical events of host defense. The involvement of leukotriene (LT) B(4) and platelet-activating factor (PAF) in TLR ligand-induced activation of inflammatory cell functions is essentially unknown.
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