temsirolimus

Also known as CCI-779, Torisel®, 42-[3-Hydroxy-2-(hydroxymethyl)-2-methylpropanoate]rapamycin, CCI 779

Temsirolimus, sold under the brand name Torisel, is an intravenous drug for the treatment of renal cell carcinoma (RCC), developed by Wyeth Pharmaceuticals and approved by the U.S. Food and Drug Administration (FDA) in May 2007, and was also approved by the European Medicines Agency (EMA) in November 2007. It is a derivative and prodrug of sirolimus.

Chemical data

Formula: C56H87NO16
Molecular weight: 1030.3 g/mol
IUPAC name: [(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl] 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate
SMILES: C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)OC(=O)C(C)(CO)CO)C)/C)O)OC)C)C)/C)OC
InChIKey: CBPNZQVSJQDFBE-FUXHJELOSA-N
XLogP: 5.6
Polar surface area: 242 Å²
H-bond donors: 4
H-bond acceptors: 16
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2007
Admin. routes: parenteral
Indications: lymphoma, myelodysplastic syndrome, renal cell carcinoma, rheumatoid arthritis

via ChEMBL · EBI

Wikidata facts

Has part: carbon
Mass: 1029.602486
Has use: medication

Show 8 more facts

chemical formula: C₅₆H₈₇NO₁₆
isomeric SMILES: C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)OC(=O)C(C)(CO)CO)C)/C)O)OC)C)C)/C)OC
canonical SMILES: CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)OC(=O)C(C)(CO)CO)C)C)O)OC)C)C)C)OC
significant drug interaction: fluconazole
subject has role: protein kinase inhibitors
medical condition treated: mantle cell lymphoma
physically interacts with: mechanistic target of rapamycin kinase
Commons category: Temsirolimus

Sources (4)

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~6 min read

Encyclopedic overview

8 sections

Contents

Mechanism of action
Efficacy
Adverse reactions
Toxicity to lungs
Dosing
See also
References
External links

{{Drugbox | Verifiedfields = changed | verifiedrevid = 409344559 | IUPAC_name = (1R,2R,4S)-4-{(2R)-2-[(3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-1,5,11,28,29-pentaoxo-1,4,5,6,9,10,11,12,13,14,21,22,23,24,25,26,27,28,29,31,32,33,34,34a-tetracosahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontin-3-yl]propyl}-2-methoxycyclohexyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate | image = Temsirolimus.svg | image_class = skin-invert-image

Excerpted from Wikipedia’s “temsirolimus” article, available under the CC BY-SA 4.0 licence.

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