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Dokumente

PZ0363

Sigma-Aldrich

CP-105,696

≥98% (HPLC)

Synonym(e):

(+)-1-(3S,4R)-[3-(4-Phenylbenzyl)-4-hydroxychroman-7-yl]cyclopentane carboxylic acid, 1-[(3S,4R)-3-([1,1′-Biphenyl]-4-ylmethyl)-3,4-dihydro-4-hydroxy-2H-1-benzopyran-7-yl]-cyclopentanecarboxylic acid, CP-105696, CP105696

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About This Item

Empirische Formel (Hill-System):
C28H28O4
CAS-Nummer:
158081-99-3
Molekulargewicht:
428.52
MDL-Nummer:
MFCD00934881
UNSPSC-Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Lagertemp.

room temp

SMILES String

OC(C1(CCCC1)C(C=C2)=CC3=C2[C@H](O)[C@@H](CC4=CC=C(C5=CC=CC=C5)C=C4)CO3)=O

Anwendung

CP-105,696 has been used as a leukotriene B4 receptor (LTB4R) antagonist to study the influence of the LTB4 pathway in the pathogenesis of acute itch flares in irritant calcipotriol (MC903)+ model allergen ovalbumin (OVA) sensitized murine model of atopic dermatitis (AD)-like disease.

Biochem./physiol. Wirkung

CP-105,696 is an orally active, potent and selective leukotriene B4 receptor (LTB4R) antagonist (IC50 against [3H]LTB4 = 5.6 nM for binding human neutrophils; IC50 = 9.7 nM & 30.3 nM, respectively using guinea pig spleen or mouse membranes) that targets LTB4R high- and low-affinity binding sites in a LTB4 non-competitive and competitive manner, respectively. CP-105,696 inhibits 5 nM LTB4-induced human neutrophils chemotaxis and CDllb upregualtion (IC50 = 5.2 nM and 430 nM, respectively) without inhibiting cyclooxygenase activity or affecting chemotaxis induced by C5a, PAF, IL-8. Oral administration is efficacious against intradermal LTB4 (100 ng/mouse), but not IL-1, injection-induced neutrophil accumulation in mice and guinea pigs (ED50 = 4.2 and 0.26 mgkg, respectively). CP-105,696 in vivo efficacy is also demonstrated in other animal models, including collagen-induced arthritis (CIA; 0.3-10 mg/kg in mice), allergic encephalomyelitis (ED50= 8.6 mg/kg; mice), and asthma (10-30 mg/kg; primate).

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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R-(+)-DIOA ≥98% (HPLC), solid

Sigma-Aldrich

D129

R-(+)-DIOA

Zafirlukast ≥98% (HPLC)

Sigma-Aldrich

Z4152

Zafirlukast

(+)-1-(3S,4R)-[3-(4-phenylbenzyl)-4-hydroxychroman-7-yl]cyclopentane carboxylic acid, a highly potent, selective leukotriene B4 antagonist with oral activity in the murine collagen-induced arthritis model.
K Koch et al.
Journal of medicinal chemistry, 37(20), 3197-3199 (1994-09-30)
C R Turner et al.
The Journal of clinical investigation, 97(2), 381-387 (1996-01-15)
To test the hypothesis that leukotriene (LT) B4 antagonists may be clinically useful in the treatment of asthma, CP-105,696 was evaluated in vitro, using chemotaxis and flow cytometry assays, and in vivo, using a primate asthma model. CP-105,696 inhibited LTB4-mediated
R J Griffiths et al.
Proceedings of the National Academy of Sciences of the United States of America, 92(2), 517-521 (1995-01-17)
Leukotriene B4 (LTB4) is a product of the 5-lipoxygenase pathway of arachidonic acid metabolism. LTB4 is a potent chemotactic factor for neutrophils and has been postulated to play an important role in a variety of pathological conditions including rheumatoid arthritis
Fang Wang et al.
Cell, 184(2), 422-440 (2021-01-16)
Itch is an evolutionarily conserved sensation that facilitates expulsion of pathogens and noxious stimuli from the skin. However, in organ failure, cancer, and chronic inflammatory disorders such as atopic dermatitis (AD), itch becomes chronic, intractable, and debilitating. In addition to

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