An internal standard for the quantification of pranlukast
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Unlabeled Version(s)
10008319Pranlukast
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Pranlukast-d4

Item No. 28709

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[4-oxo-2-(1H-tetrazol-5-yl)-4H-1-benzopyran-8-yl]-4-(4-phenylbutoxy)-benzamide-d4
CAS Number
2713172-43-9
Molecular Formula
C27H19D4N5O4
Formula Weight
485.5
Purity
≥99% deuterated forms (d1-d4)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=C1C=C(C2=NN=NN2)OC(C1=CC=C3)=C3NC(C4=C([2H])C([2H])=C(C([2H])=C4[2H])OCCCCC5=CC=CC=C5)=O
InChi Code
InChI=1S/C27H23N5O4/c33-23-17-24(26-29-31-32-30-26)36-25-21(23)10-6-11-22(25)28-27(34)19-12-14-20(15-13-19)35-16-5-4-9-18-7-2-1-3-8-18/h1-3,6-8,10-15,17H,4-5,9,16H2,(H,28,34)(H,29,30,31,32)/i12D,13D,14D,15D
InChi Key
NBQKINXMPLXUET-YTAQVSDTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $436

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    Product Description

    Pranlukast-d4 is intended for use as an internal standard for the quantification of pranlukast (Item No. 10008319) by GC- or LC-MS. Pranlukast is an orally bioavailable cysteinyl leukotriene 1 (CysLT1) receptor antagonist (IC50s = 4.3-7.2 nM in radioligand binding assays).1 It is selective for the CysLT1 receptor over the CysLT2 receptor (IC50 = 3,620 nM for the human receptor).2 Pranlukast inhibits mucus secretion induced by leukotriene D4 (LTD4; Item No. 20310) in isolated guinea pig trachea with an IC50 value of 0.3 µM.3 It inhibits TNF-α-induced NF-ĸB p65 nuclear localization in U937 and Jurkat cells when used at concentrations of 10 and 100 µM.4 Pranlukast inhibits bronchoconstriction induced by LTC4 (Item No. 20210), LTD4, and LTE4 (Item No. 20410), but not LTB4 (Item No. 20110), in guinea pigs (ID50s = 0.8, 1, 0.7, and >500 µg/kg, respectively).5 It reduces cortical infarct volume by 81.6% and decreases neuronal death in the cortex, hippocampus, and striatum in a rat model of ischemia induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 0.03 mg/kg.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lynch, K.R., O'Neill, G.P., Liu, Q., et al. Characterization of the human cysteinyl leukotriene CysLT1 receptor. Nature 399(6738), 789-793 (1999).

    2. Heise, C.E., O'Dowd, B.F., Figueroa, D.J., et al. Characterization of the human cysteinyl leukotriene 2 receptor. The Journal of Biological Chemisty 275(39), 30531-30536 (2000).

    3. Liu, Y.-C., Khawaja, A.M., and Rogers, D.F. Effects of the cysteinyl leukotriene receptor antagonists pranlukast and zafirlukast on tracheal mucus secretion in ovalbumin-sensitized guinea-pigs in vitro. Br. J. Pharmacol. 124(3), 563-571 (1998).

    4. Ichiyama, T., Hasegawa, S., Umeda, M., et al. Pranlukast inhibits NF-KB activation in human monocytes/macrophages and T cells. Clin. Exp. Allergy 33(6), 802-807 (2003).

    5. Nakai, H., Konno, M., Kosuge, S., et al. New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships. J. Med. Chem. 31(1), 84-91 (1988).

    6. Zhang, W.-P., Wei, E.-Q., Mei, R.-H., et al. Neuroprotective effect of ONO-1078, a leukotriene receptor antagonist, on focal cerebral ischemia in rats. Acta Pharmacol. Sin. 23(10), 871-877 (2002).