Description
Rapamycin is a natural macrolide immunosuppressant that activates mTORC1. Seco Rapamycin (sodium salt) is a nonenzyme-
dependent degradation product of rapamycin resulting from ester hydration followed by dehydration. It has less than 4% of the potency of rapamycin in a thymocyte proliferation assay. Rapamycin quickly degrades to two ring-
opened products, including seco rapamycin, in the cytoplasm or in homogenates of Caco-
2 cells. Like rapamycin, seco rapamycin is secreted from cells by P-
glycoprotein and metabolized to a common dihydro species. While seco rapamycin poorly activates mTOR, it mimics rapamycin in its ability to inhibit the proteasome.
Chemical Properties
Yellow Solid
Uses
A metabolite of Sirolimus
Uses
A decomposition product of Rapamycin (R124000).
References
[1] C. P. WANG. High Performance Liquid Chromatographic Isolation, Spectroscopic Characterization, and Immunosuppressive Activities of Two Rapamycin Degradation Products[J]. Journal of Liquid Chromatography & Related Technologies, 1994, 17 1: 3383-3392. DOI:
10.1080/10826079408013519[2] PAINE M, LEUNG L, LIM H, et al. Identification of a novel route of extraction of sirolimus in human small intestine: roles of metabolism and secretion.[J]. The Journal of Pharmacology and Experimental Therapeutics, 2002, 11 1: 0. DOI:
10.1124/jpet.301.1.174[3] MARY F PAINE Paul B W Louis Y Leung. New insights into drug absorption: studies with sirolimus.[J]. Therapeutic Drug Monitoring, 2004, 26 5: 463-467. DOI:
10.1097/00007691-200410000-00001[4] PAWEL A OSMULSKI M G. Rapamycin allosterically inhibits the proteasome.[J]. Molecular Pharmacology, 2013, 84 1: 104-113. DOI:
10.1124/mol.112.083873
