Rapamycin

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Product Details
Synonyms Sirolimus; Rapamune; NSC 226080; Antibiotic AY-22989; WY-090217; RAPA; SILA 9268A; CCRIS 9024
Product Type Chemical
Properties
Formula C51H79NO13
MW 914.2
Merck Index 14: 8114
CAS 53123-88-9
RTECS VE6250000
Source/Host Chemicals Isolated from Streptomyces hygroscopicus.
Purity Chemicals ≥98%
Appearance White to off-white solid.
Solubility Soluble in DMSO, methanol or chloroform.
InChi Key QFJCIRLUMZQUOT-KIHCOMIKSA-N
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
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Product Specification Sheet
Datasheet Download PDF
  • Antibiotic.
  • Antibacterial and antifungal properties [1, 2].
  • Forms a complex with FKBP12 and inhibits the mammalian target of rapamycin (mTOR). Inhibits the response to interleukin-2 (IL-2), and thereby blocks activation of T and B cells [3, 5, 6, 11].
  • Potent immunosuppressant [4, 10] used as an alternative to calcineurin inhibitors [12].
  • Restricts the proliferation of smooth-muscle cells by blocking cell cycle progression at the G1/S transition [7, 13].
  • Anti-proliferative. Antitumor compound [14, 15].
  • Apoptosis enhancer. Activator of autophagy both in vitro and in vivo [8, 9].
  • Anti-HIV and anti-aging compound [16, 17].
  • Neuroprotective [18].
  • Suppressor for self-renewal and vascular differentiation potential in hemangioma stem cells [19].
  • mTORC1 inhibitor [20].
Product References
  1. Rapamycin (AY-22,989), a new antifungal antibiotic. I. Taxonomy of the producing streptomycete and isolation of the active principle: C. Vezina, et al.; J. Antibiot. (Tokyo) 28, 721 (1975)
  2. Rapamycin (AY-22,989), a new antifungal antibiotic. II. Fermentation, isolation and characterization: S.N. Sehgal, et al.; J. Antibiot. (Tokyo) 28, 727 (1975)
  3. Inhibition of T and B lymphocyte proliferation by rapamycin: J.E. Kay, et al.; Immunology 72, 544 (1991)
  4. FK506 and rapamycin: novel pharmacological probes of the immune response: J.Y. Chang, et al.; TIPS 12, 218 (1991) (Review)
  5. Rapamycin-FKBP specifically blocks growth-dependent activation of and signaling by the 70 kd S6 protein kinases: J. Chung, et al.; Cell 69, 1227 (1992),
  6. Rapamycin inhibition of interleukin-2-dependent p33cdk2 and p34cdc2 kinase activation in T lymphocytes: W.G. Morice, et al.; J. Biol. Chem. 268, 22737 (1993)
  7. A mammalian protein targeted by G1-arresting rapamycin-receptor complex: E.J. Brown, et al.; Nature 369, 756 (1994)
  8. Rapamycin, a potent immunosuppressive drug, causes programmed cell death in B lymphoma cells: S. Muthukkumar, et al.; Transplantation 60, 264 (1995)
  9. Rapamycin enhances apoptosis and increases sensitivity to cisplatin in vitro: Y. Shi, et al.; Cancer Res. 55, 1982 (1995)
  10. Mechanism of action of the immunosuppressant rapamycin: F.J. Dumont & Q. Su; Life Sci. 58, 373 (1996) (Review)
  11. Rapamycin causes poorly reversible inhibition of mTOR and induces p53- independent apoptosis in human rhabdomyosarcoma cells: H. Hosoi, et al.; Cancer Res. 59, 886 (1999)
  12. Rapamycin in transplantation: a review of the evidence: R.N. Saunders, et al.; Kidney Int. 59, 3 (2001) (Review)
  13. Rapamycin in cardiovascular medicine: P.N. Ruygrok, et al.; Intern. Med. J. 33, 103 (2003) (Review)
  14. Rapamycin: an anti-cancer immunosuppressant?: B.K. Law; Crit. Rev. Oncol. Hematol. 56, 47 (2005) (Review)
  15. Tubers and tumors: rapamycin therapy for benign and malignant tumors: D.R. Plas & G. Thomas; Curr. Opin. Cell Biol. 21, 230 (2009) (Review)
  16. Potential use of rapamycin in HIV infection: M. Donia, et al.; Br. J. Clin. Pharmacol. 70, 784 (2010) (Review)
  17. Resveratrol and rapamycin: are they anti-aging drugs? M. Kaeberlein; Bioessays 32, 96 (2010)
  18. Fighting neurodegeneration with rapamycin: mechanistic insights: J. Bové, et al.; Nat. Rev. Neurosci. 12, 437 (2011) (Review)
  19. Rapamycin suppresses self-renewal and vasculogenic potential of stem cells isolated from infantile hemangioma: S. Greenberger, et al.; J. Invest. Dermatol. 131, 2467 (2011)
  20. Inhibition of the PI3K–Akt and mTORC1 signaling pathways promotes the elongation of vascular endothelial cells: K. Tsuji-Tamura & M. Ogawa; J. Cell Sci. 129, 1165 (2016)
  21. Chemically defined and growth-factor-free culture system for the expansion and derivation of human pluripotent stem cells: S. Yasuda, et al.; Nature Biomed. Eng. 2, 173 (2018)
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