Rapamycin

Rapamycin

Cayman Chemical Item Number 13346

Sirolimus (CAS 53123-88-9)

Rapamycin (CAS 53123-88-9)

Description

Rapamycin is an immunosuppressant that is used primarily to prevent the rejection of organ and bone marrow transplant. It was first described as a potent inhibitor of interleukin-2 activation of lymphocytes (IC₅₀ = 5 pM).¹ It is now known that rapamycin specifically interacts with the cytosolic FK-binding protein 12 (FKBP12) to form a complex which inhibits the mammalian target of rapamycin (mTOR) pathway by directly binding to mTOR Complex 1 (mTORC1). Rapamycin and other inhibitors of mTORC1 signaling show potential in treating cancer, adipogenesis, diabetes, tuberous sclerosis, and cardiovascular disease.^2,3,4

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

2 Akcakanat, A., Zhang, L., Tsavachidis, S., et al. The rapamycin-regulated gene expression signature determines prognosis for breast cancer. Mol Cancer 8(75) (2009).

3 Zhang, H.H., Huang, J., Düvel, K., et al. Insulin stimulates adipogenesis through the Akt-TSC2-mTORC1 pathway. PLoS One 4(7) (2009).

4 Balgi, A.D., Fonseca, B.D., Donohue, E., et al. Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling. PLoS One 4(9) (2009).

Synonyms

Sirolimus

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

Molecular Formula

C₅₁H₇₉NO₁₃

Formula Weight

914.2

Formulation

A crystalline solid

Purity

≥95%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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O=C(C(N1[C@H](C(O[C@H]([C@@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC([C@H](C)/C=C(C)/[C@@H](O)[C@@H](OC)C([C@@H]3C)=O)=O)=O)CCCC1)=O)[C@]4(O)O[C@H](C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C3)CC[C@H]4C

Background Reading

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

Zhang, H.H., Huang, J., Düvel, K., et al. Insulin stimulates adipogenesis through the Akt-TSC2-mTORC1 pathway. PLoS One 4(7) (2009).

Balgi, A.D., Fonseca, B.D., Donohue, E., et al. Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling. PLoS One 4(9) (2009).

Akcakanat, A., Zhang, L., Tsavachidis, S., et al. The rapamycin-regulated gene expression signature determines prognosis for breast cancer. Mol Cancer 8(75) (2009).

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Rapamycin (CAS 53123-88-9)

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Rapamycin

Rapamycin (CAS 53123-88-9)

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