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PZ0020 Sigma-Aldrich

Temsirolimus

≥98% (HPLC)

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

  • CAS Number 162635-04-3

  • Empirical Formula (Hill Notation) C56H87NO16

  • Molecular Weight 1030.29

  •  MDL number MFCD00934421

  •  PubChem Substance ID 329823687

  •  NACRES NA.77

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Autophagy, Autophagy Activators, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
mfr. no.   Pfizer®
color   white to off-white
solubility   DMSO: ≥20 mg/mL
originator   Pfizer
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)

Description

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

Packaging

5, 25 mg in glass bottle

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.

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®Pfizer), a collection of 90 Pfizer-developed drugs and research tools. Click here to learn more.

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.

Other Notes

This compound was developed by Pfizer for Kinase Phosphatase Biology research. To learn more about Sigma′s partnership with Pfizer and view other authentic, high-quality Pfizer compounds, visit sigma.com/bsm-pfizer.

To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold for research purposes under agreement from Pfizer Inc.

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pfizer is a registered trademark of Pfizer, Inc.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Oncogenes and Tumor Suppressors Reprogram Metabolism

Proliferating cells require the biosynthesis of structural components for biomass production and for genomic replication. This requires a reprogramming of the metabolic pathways to ensure nutrients s...
BioFiles v7 n4
Keywords: Aerobic, Antitumor agents, Apoptosis, Cancer, Citric Acid Cycle, Degradations, Environmental, Gene expression, Glycolysis, Growth factors, Metabolic Pathways, Metabolism, Metabolites, Nucleotide Synthesis, Pentose phosphate pathway, Phosphorylations

PKB/Akt

The PDK1–PKB/Akt axis represents one of the most actively researched cell signaling pathways. This protein kinase cascade is known to play a central role in mediating the actions of a range of stimul...
Keywords: Apoptosis, Atomic absorption spectroscopy, Cancer, Cell proliferation, Cell signaling, Diabetes, Gene expression, Growth factors, Inflammation, Metabolism, Myristoylations, Phosphorylations, Reversible addition-fragmentation chain transfer polymerizations

Pfizer Compounds for Kinase Phosphatase Biology

From our library of Articles, Sigma-Aldrich presents Pfizer Compounds for Kinase Phosphatase Biology

UHPLC Analysis of Temsirolimus and Sirolimus on Titan™ C18

From our library of Articles, Sigma-Aldrich presents UHPLC Analysis of Temsirolimus and Sirolimus on Titan™ C18
Keywords: Chromatography, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Pharmaceutical, Solvents

UHPLC Analysis of Temsirolimus on Titan™ C18

From our library of Articles, Sigma-Aldrich presents UHPLC Analysis of Temsirolimus on Titan™ C18
Keywords: Chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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