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Merck

PZ0020

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:
162635-04-3
Molecular Weight:
1030.29
NACRES:
NA.77
PubChem Substance ID:
329823687
UNSPSC Code:
12352200
MDL number:
MFCD00934421

Product Name

Temsirolimus, ≥98% (HPLC)

InChI key

CBPNZQVSJQDFBE-FUXHJELOSA-N

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

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

Quality Level

100

Gene Information

human ... FKBP1A(2280)

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.

General description

Temsirolimus is an esterified rapamycin compound, soluble in water.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000357802
0000357802
0000295421
0000295421
0000189194

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Viktor Grünwald et al.
European urology, 70(6), 1006-1015 (2016-05-31)
The predictive role of objective remission remains undefined for targeted agents in metastatic renal cell carcinoma (mRCC); however, early tumour shrinkage (eTS) was shown to be predictive and/or prognostic for overall survival (OS) and progression-free survival (PFS) in mRCC in
C Le Tourneau et al.
British journal of cancer, 99(8), 1197-1203 (2008-09-18)
The proof of principle that a drug targeting mTOR can improve survival has been obtained recently from a large randomised trial using temsirolimus as a first-line therapy in patients with advanced poor prognostic renal cell carcinoma. Consistent data have recently
Cynthia Guilbert et al.
PloS one, 8(12), e85995-e85995 (2014-01-07)
Inhibitors of the mammalian target of rapamycin (mTORi) have clinical activity; however, the benefits of mTOR inhibition by rapamycin and rapamycin-derivatives (rapalogs) may be limited by a feedback mechanism that results in AKT activation. Increased AKT activity resulting from mTOR
Temsirolimus, interferon alfa, or both for advanced renal-cell carcinoma
Hudes G, et al.
The New England Journal of Medicine, 356(22), 2271-2281 (2007)
Temsirolimus
Ma WW and Jimeno A
Drugs Today (Barc), 43(10), 659-669 (2007)
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