An allosteric inhibitor of mTORC1
Related Products
Labeled Version(s)
22093Rapamycin-d3
Pro-drug Form(s)
13671Wortmannin-Rapamycin Conjugate
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Rapamycin

Item No. 13346

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7E,15E,17E,19E)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34aS-Hexadecahydro-9R,27-dihydroxy-3S-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10R,21S-dimethoxy-6R,8,12R,14S,20,26R-hexamethyl-23S,27R-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
CAS Number
53123-88-9
Synonyms
  • AY 22989
  • NSC 226080
  • Sirolimus
  • Wy 090217
Molecular Formula
C51H79NO13
Formula Weight
914.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 0.25 mg/ml
λmax
268, 278, 289 nm
SMILES
O=C([C@]1([H])CCCCN1C(C([C@@]2(O)[C@H](C)CC[C@](C[C@H](OC)/C(C)=C/C=C/C=C/[C@H](C3)C)([H])O2)=O)=O)O[C@](CC([C@H](C)/C=C(C)/[C@@H](O)[C@@H](OC)C([C@@H]3C)=O)=O)([H])[C@H](C)C[C@H]4C[C@@H](OC)[C@H](O)CC4
InChi Code
InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
InChi Key
QFJCIRLUMZQUOT-HPLJOQBZSA-N
Origin
Bacterium/Streptomyces hygroscopicus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $43

    Add

    5 mg

    $108

    Add

    10 mg

    $194

    Add

    25 mg

    $429

    Add
    Cayman Chemical
    Explore Obesity & Metabolic Disease Resources

    Discover high-quality research tools to investigate GLP-1 mechanisms and next-generation metabolic targets.

    OBESITY RESEARCH SOLUTIONS
    Product Description

    Rapamycin is an allosteric inhibitor of the mammalian target of rapamycin (mTOR) complex 1 (mTORC1) originally isolated from S. hygroscopicus.1 It interacts with FKBP prolyl isomerase 1A (FKBP12) to form a complex that binds to and inhibits the kinase activity of mTORC1. Rapamycin inhibits growth of Rh1 and Rh30 rhabdomyosarcoma cells in serum-free medium, with 50% inhibition observed at concentrations of 0.1 and 0.5 ng/ml, respectively, and increases apoptosis in these cells at 100 ng/ml.2 It also induces autophagy in a variety of cell types.1 Rapamycin inhibits IL-2-induced proliferation of IL-2-dependent T cells by 50% when used at concentrations less than 5 pM.3 Formulations containing rapamycin have been used as immunosuppressive agents in the prevention of organ transplant rejection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, Y.C., and Guan, K.-L. mTOR: A pharmacological target for autophagy regulation. J. Clin. Invest. 125(1), 25-32 (2015).

    2. Hosoi, H., Dilling, M.B., Shikata, T., et al. Rapamycin causes poorly reversible inhibition of mTOR and induces p53-independent apoptosis in human rhabdomyosarcoma cells. Cancer Res. 59(4), 886-894 (1999).

    3. Kay, J.E., Kromwel, L., Doe, S.E.A., et al. Inhibition of T and B lymphocyte proliferation by rapamycin. Immunology 72(4), 544-549 (1991).

    Product Citations

    Chen, J., Wang, Q., Feng, X., et al. Umbilical cord-derived mesenchymal stem cells suppress autophagy of T cells in patients with systemic lupus erythematosus via transfer of mitochondria. Stem Cells Int. 2016, 4062789 (2016).

    Reinke, E.N., Ekoue, D.N., Bera, S., et al. Translational regulation of GPx-1 and GPx-4 by the mTOR pathway. PLOS One 9(4), e93472 (2014).

    Gharibi, B., Ghuman, M.S., and Hughes, F.J. Akt- and Erk-mediated regulation of proliferation and differentiation during PDGFRβ-induced MSC self-renewal. J. Cell. Mol. Med. 16(11), 2789-2801 (2012).

    Kapoor, V., Zaharieva, M.M., Das, S.N., et al. Erufosine simultaneously induces apoptosis and autophagy by modulating the Akt-mTOR signaling pathway in oral squamous cell carcinoma. Cancer Lett. 319(1), 39-48 (2012).

    Lu, C.-H., Liu, Y.-W., Hua, S.-C., et al. Autophagy induction of reversine on human follicular thyroid cancer cells. Biomed. Pharmacother. 66(8), 642-647 (2012).

    Zhang, Y., Xu, S., Lin, J., et al. mTORC1 is a target of nordihydroguaiaretic acid to prevent breast tumor growth in vitro and in vivo. Breast Cancer Res. Treat. 136(2), 379-388 (2012).