XL-388

XL-388
Identifiers
IUPAC name
  • [7-(6-aminopyridin-3-yl)-3,5-dihydro-2H-1,4-benzoxazepin-4-yl]-(3-fluoro-2-methyl-4-methylsulfonylphenyl)methanone
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC23H22FN3O4S
Molar mass455.50 g·mol−1
3D model (JSmol)
SMILES
  • CC1=C(C=CC(=C1F)S(=O)(=O)C)C(=O)N2CCOC3=C(C2)C=C(C=C3)C4=CN=C(C=C4)N
InChI
  • InChI=1S/C23H22FN3O4S/c1-14-18(5-7-20(22(14)24)32(2,29)30)23(28)27-9-10-31-19-6-3-15(11-17(19)13-27)16-4-8-21(25)26-12-16/h3-8,11-12H,9-10,13H2,1-2H3,(H2,25,26)
  • Key:LNFBAYSBVQBKFR-UHFFFAOYSA-N

XL-388 is a drug which acts as a potent and selective inhibitor of both subtypes of the mechanistic target of rapamycin (mTOR), mTORC1 and mTORC2.[1] It is being researched for the treatment of various forms of cancer,[2][3][4] and has also been used to demonstrate a potential application for mTOR inhibitors in the treatment of neuropathic pain.[5][6]

References

  1. ↑ Takeuchi CS, Kim BG, Blazey CM, Ma S, Johnson HW, Anand NK, et al. (March 2013). "Discovery of a novel class of highly potent, selective, ATP-competitive, and orally bioavailable inhibitors of the mammalian target of rapamycin (mTOR)". Journal of Medicinal Chemistry. 56 (6): 2218–34. doi:10.1021/jm3007933. PMID 23394126.
  2. ↑ Zhu YR, Zhou XZ, Zhu LQ, Yao C, Fang JF, Zhou F, et al. (August 2016). "The anti-cancer activity of the mTORC1/2 dual inhibitor XL388 in preclinical osteosarcoma models". Oncotarget. 7 (31): 49527–49538. doi:10.18632/oncotarget.10389. PMC 5226526. PMID 27385099.
  3. ↑ Xiong Z, Zang Y, Zhong S, Zou L, Wu Y, Liu S, et al. (May 2017). "The preclinical assessment of XL388, a mTOR kinase inhibitor, as a promising anti-renal cell carcinoma agent". Oncotarget. 8 (18): 30151–30161. doi:10.18632/oncotarget.15620. PMC 5444733. PMID 28404914.
  4. ↑ Zhong S, Xue J, Cao JJ, Sun B, Sun QF, Bian LG, et al. (November 2020). "The therapeutic value of XL388 in human glioma cells". Aging. 12 (22): 22550–22563. doi:10.18632/aging.103791. PMC 7746352. PMID 33159013.
  5. ↑ Choi S, Kim K, Cha M, Kim M, Lee BH (January 2020). "mTOR signaling intervention by Torin1 and XL388 in the insular cortex alleviates neuropathic pain". Neuroscience Letters. 718: 134742. doi:10.1016/j.neulet.2020.134742. PMID 31917234.
  6. ↑ Cha M, Choi S, Kim K, Lee BH (November 2020). "Manganese-enhanced MRI depicts a reduction in brain responses to nociception upon mTOR inhibition in chronic pain rats". Molecular Brain. 13 (1): 158. doi:10.1186/s13041-020-00687-1. PMC 7713325. PMID 33267907.
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