A degradation product of rapamycin
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Seco Rapamycin (sodium salt)

Item No. 16158

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[2R-[2α,2(S*),3α,6β[2S*,3E,5E,7E,9S*,11R*,13R*,14R*,15E,7R*,19E,21R*,22(1S*,3R*,4R*)]]]-1-[oxo[tetrahydro-2-hydroxy-6-[14-hydroxy-22-(4-hydroxy-3methoxycyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaenyl]-3-methyl-2H-pyran-2-yl]acetyl]-2-piperidinecarboxylic acid, monosodium salt
CAS Number
148554-65-8
Molecular Formula
C51H78NO13 • Na
Formula Weight
936.2
Purity
≥85%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
277, 289 nm
SMILES
O[C@@H]1CC[C@@H](C[C@@H](C)/C=C/C([C@H](C)/C=C(C)/[C@@H](O)[C@@H](OC)C([C@H](C)C[C@H](C)/C=C/C=C/C=C([C@@H](OC)C[C@@H]2CC[C@@H](C)[C@](O)(C(C(N3CCCC[C@H]3C([O-])=O)=O)=O)O2)\C)=O)=O)C[C@H]1OC.[Na+]
InChi Code
InChI=1S/C51H79NO13.Na/c1-31(26-35(5)45(55)47(64-10)46(56)36(6)28-34(4)41(53)23-19-32(2)27-38-21-24-42(54)44(29-38)63-9)16-12-11-13-17-33(3)43(62-8)30-39-22-20-37(7)51(61,65-39)48(57)49(58)52-25-15-14-18-40(52)50(59)60;/h11-13,16-17,19,23,28,31-32,34-35,37-40,42-44,46-47,54,56,61H,14-15,18,20-22,24-27,29-30H2,1-10H3,(H,59,60);/q;+1/p-1/b13-11+,16-12+,23-19+,33-17+,36-28+;/t31-,32+,34-,35-,37-,38+,39+,40+,42-,43+,44-,46-,47+,51-;/m1./s1
InChi Key
DNMSBJYMPJMFNS-OWGFPTNRSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Rapamycin (Item No. 13346) is a natural macrolide immunosuppressant that activates mTORC1. Seco rapamycin (sodium salt) is a nonenzyme-dependent degradation product of rapamycin (Item No. 13346) resulting from ester hydration followed by dehydration.1 It has less than 4% of the potency of rapamycin in a thymocyte proliferation assay.1 Rapamycin quickly degrades to two ring-opened products, including seco rapamycin, in the cytoplasm or in homogenates of Caco-2 cells.2 Like rapamycin, seco rapamycin is secreted from cells by P-glycoprotein and metabolized to a common dihydro species.3 While seco rapamycin poorly activates mTOR, it mimics rapamycin in its ability to inhibit the proteasome.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, C.P., Chan, K.W., Schiksnis, R.A., et al. High performance liquid chromatographic isolation, spectroscopic characterization, and immunosuppressive activities of two rapamycin degradation products. J. Liq. Chromatogr. 17(16), 3383-3392 (1994).

    2. Paine, M.F., Leung, L.Y., Lim, H.K., et al. Identification of a novel route of extraction of sirolimus in human small intestine: Roles of metabolism and secretion. J. Pharmacol. Exp. Ther. 301(1), 174-186 (2002).

    3. Paine, M.F., Leung, L.Y., and Watkins, P.B. New insights into drug absorption: Studies with sirolimus. Ther. Drug Monit. 26(5), 463-467 (2004).

    4. Osmulski, P.A., and Gaczynska, M. Rapamycin allosterically inhibits the proteasome. Mol. Pharmacol. 84(1), 104-113 (2013).