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Key Documents

PZ0020

Sigma-Aldrich

Temsirolimus

≥98% (HPLC)

Synonym(s):

42-[3-Hydroxy-2-(hydroxymethyl)-2-methylpropanoate]-rapamycin, CCI-779

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About This Item

Empirical Formula (Hill Notation):
C56H87NO16
CAS Number:
Molecular Weight:
1030.29
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

SMILES string

CO[C@@H]1CC(CC[C@H]1OC(=O)C(C)(CO)CO)C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](CC3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCCC4C(=O)O2)OC

InChI

1S/C56H87NO16/c1-33-17-13-12-14-18-34(2)45(68-9)29-41-22-20-39(7)56(67,73-41)51(63)52(64)57-24-16-15-19-42(57)53(65)71-46(30-43(60)35(3)26-38(6)49(62)50(70-11)48(61)37(5)25-33)36(4)27-40-21-23-44(47(28-40)69-10)72-54(66)55(8,31-58)32-59/h12-14,17-18,26,33,35-37,39-42,44-47,49-50,58-59,62,67H,15-16,19-25,27-32H2,1-11H3/b14-12+,17-13+,34-18+,38-26+/t33-,35-,36-,37-,39-,40+,41+,42+,44-,45+,46+,47-,49-,50+,56-/m1/s1

InChI key

CBPNZQVSJQDFBE-FUXHJELOSA-N

Gene Information

human ... FKBP1A(2280)

General description

Temsirolimus is an esterified rapamycin compound, soluble in water.

Application

Temsirolimus has been used:
  • in combination with radiation to study its effect on von Hippel Lindau (VHL) tumour suppressor gene-deficient renal carcinoma cell lines
  • to induce autophagy
  • as a mammalian target of rapamycin complex 1 (mTORC1) inhibitor to study the effect of cellular Akt-kinase on human papillomaviruses 16 (HPV16) late gene expression

Biochem/physiol Actions

Temsirolimus is a specific inhibitor of mammalian target of rapamycin (mTOR) mTOR Complex 1 (mTORC1). Temsirolimus is an antiproliferative and antiangiogenic, the first-in-class mTOR inhibitor approved for the treatment of patients with advanced poor prognosis renal cell carcinoma.
Temsirolimus is an antiproliferative and antiangiogenic mTORC1 inhibitor.
The inhibitory action of temsirolimus is mediated by FKBP-12 (FK506-binding protein 12), a major intracellular protein. It is useful in treating renal-cell carcinoma.

Features and Benefits

This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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