Israpafant

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Israpafant
Israpafant.svg
Systematic (IUPAC) name
(6R)-4-(2-Chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
Clinical data
Legal status
  • Investigational New Drug
Identifiers
CAS Number 117279-73-9 YesY
PubChem CID: 636426
ChemSpider 552203
Chemical data
Formula C28H29ClN4S
Molecular mass 489.074 g/mol
  • C[C@@H]1C2=NN=C(N2C3=C(C=C(S3)CCC4=CC=C(C=C4)CC(C)C)C(=N1)C5=CC=CC=C5Cl)C
  • InChI=1S/C28H29ClN4S/c1-17(2)15-21-11-9-20(10-12-21)13-14-22-16-24-26(23-7-5-6-8-25(23)29)30-18(3)27-32-31-19(4)33(27)28(24)34-22/h5-12,16-18H,13-15H2,1-4H3/t18-/m1/s1
  • Key:RMSWMRJVUJSDGN-GOSISDBHSA-N

Israpafant (Y-24180) is a drug which acts as a selective antagonist for the platelet-activating factor receptor,[1] and was originally developed for the treatment of asthma.[2] Its chemical structure is a thienotriazolodiazepines, closely related to the sedative benzodiazepine derivative etizolam. However israpafant binds far more tightly to the platelet-activating factor receptor, with an IC50 of 0.84nM for inhibiting PAF-induced human platelet aggregation (compared to etizolam's IC50 of 998nM at this target), while it binds only weakly to benzodiazepine receptors, with a Ki of 3680nM.[3] Israpafant has been found to inhibit the activation of eosinophil cells,[4][5][6] and consequently delays the development of immune responses. It has also been shown to have anti-nephrotoxic properties,[7] and to mobilize calcium transport.[8]


See also

References

  1. ↑ Hirota N, Yasuda D, Hashidate T, Yamamoto T, Yamaguchi S, Nagamune T, Nagase T, Shimizu T, Nakamura M. Amino acid residues critical for endoplasmic reticulum export and trafficking of platelet-activating factor receptor. Journal of Biological Chemistry. 2010 Feb 19;285(8):5931-40. doi: 10.1074/jbc.M109.066282. PMID 20007715
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Komatsu H, Amano M, Yamaguchi S, Sugahara K. Inhibition of activation of human peripheral blood eosinophils by Y-24180, an antagonist to platelet-activating factor receptor. Life Sciences. 1999;65(13):PL171-6. PMID 10503965
  5. ↑ Mizuki M, Komatsu H, Akiyama Y, Iwane S, Tsuda T. Inhibition of eosinophil activation in bronchoalveolar lavage fluid from atopic asthmatics by Y-24180, an antagonist to platelet-activating factor. Life Sciences. 1999;65(20):2031-9. PMID 10579457
  6. ↑ Satoh T, Tahara E, Yamada T, Watanabe C, Itoh T, Terasawa K, Nagai H, Saiki I. Differential effect of antiallergic drugs on IgE-mediated cutaneous reaction in passively sensitized mice. Pharmacology. 2000 Feb;60(2):97-104. PMID 10657759
  7. ↑ Kawaguchi A, Sugimoto K, Fujimura A. Preventive effect of platelet-activating factor antagonist, Y-24180, against cyclosporine-induced acute nephrotoxicity. Life Sciences. 2001 Jan 26;68(10):1181-90. PMID 11228102
  8. ↑ Chao YY, Jan CR. Effect of Y-24180 on Ca2+ movement and proliferation in renal tubular cells. Life Sciences. 2004 Jan 2;74(7):923-33. PMID 14659980


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