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IPI-504 (Retaspimycin hydrochloride)

In stock
Catalog No.
A4061
Hsp90 inhibitor,novel, potent,selective
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$350.00
In stock
5mg
$175.00
In stock
10mg
$315.00
In stock
50mg
$795.00
In stock
100mg
$1,395.00
In stock

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Background

Retaspimycin hydrochloride (also known as IPI-504), a hydroquinone hydrochloride salt derivative of 17-AAG, is a novel, potent and selective inhibitor of heat shock protein 90(Hsp90) that binds to the amino-terminal ATP/ADP-binding site of Hsp90. As a highly water-soluble version of 17-AAG, IPI-504 (solubility > 200 mg/mL) does not need prior dissolution in organic solvents and hence can be delivered in high concentrations. Once in the systemic circulation, IPI-504 is deprotonated and converted into the free base IPI-504 which is subsequently oxidized to 17-AAG. IPI-504 potently inhibits proliferation in several tumor cell lines with 50% inhibition concentration IC50 values ranging from 10-40 nmol/L and has been used for the treatment of gastrointestinal stromal tumors, soft-tissue sarcomas and non-small cell lung cancer.

Reference

Britt Erika Hanson and David H Vesole. Retaspimycin hydrochloride (IPI-504): a novel heat shock protein inhibitor as an anticancer agent. Expert Opin. Investi. Drugs (2009) 18(9): 1375-1383

David Siegel, Sundar Jagannath, David H. Vesole, Ivan Borello, Amitabha Mazumder, Constantine Mitsiades, Jill Goddard, Joi Dunbar, Emmanuel Normant, Julian Adams, David Grayzel, Kenneth C. Anderson and Paul Richardson. A phase 1 study of IPI-504 (retaspimycin hydrochloride) in patients with relapsed or relapsed and refractory multiple myeloma. Leukemia & Lymphoma, 2011; 52(12): 2308-2315

Ching Ching Leow, Jon Chesebrough, Karen T. Coffman, Christine A. Fazenbaker, John Gooya, David Weng, Steve Coats, Dowdy Jackson, Bahija Jallal and Yong Chang. Antitumor efficacy of IPI-504, a selective heat shock protein 90 inhibitor against human epidermal growth factor receptor 2-positive human xenograft models as a single agent and in combination with trastuzumab or lapatinib. Mol Cancer Ther 2009; 8: 2131-2141

Product Citation

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt624.2
Cas No.857402-63-2
FormulaC31H46ClN3O8
SynonymsIPI 504, IPI504
Solubility≥26.1 mg/mL in DMSO with gentle warming, ≥100 mg/mL in EtOH with ultrasonic, <2.5 mg/mL in H2O
Chemical Name[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6,20,22-trihydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16-oxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(22),8,12,14,18,20-hexaen-10-yl] carbamate;hydrochloride
SDFDownload SDF
Canonical SMILESCC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=C(C(=C2O)C1)NCC=C)O)C)OC)OC(=O)N)C)C)O)OC.Cl
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Protocol

Cell experiment [1]:

Cell lines

Glioma cell lines (D-54 MG and U-251 MG cells)

Preparation method

This compound was soluble in DMSO. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reaction Conditions

1 or 2.5 μM; 24 or 48 hrs

Applications

In glioma cells, IPI-504 inhibited cell proliferation through increasing sub-G1 population of cells and dose-dependently inducing fragmented DNA of the apoptotic cells.

Animal experiment [1]:

Animal models

Mice bearing human brain tumor D-54MG xenografts

Dosage form

100 mg/kg; i.p.; b.i.d., twice weekly or 5/2/5 schedule (5 days on, 2 days off, and then 5 days on), for 6 weeks

Applications

In immunocompromised mice, IPI-504 mildly attenuated tumor growth.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Di K, Keir ST, Alexandru-Abrams D, Gong X, Nguyen H, Friedman HS, Bota DA. Profiling Hsp90 differential expression and the molecular effects of the Hsp90 inhibitor IPI-504 in high-grade glioma models. J Neurooncol. 2014 Dec;120(3):473-81.

Biological Activity

Description Retaspimycin Hcl(IPI504 Hcl) is a small-molecule inhibitor of heat shock protein 90 (HSP90) with antiproliferative and antineoplastic activities.
Targets HSP90          
IC50            

Quality Control

Chemical structure

IPI-504 (Retaspimycin hydrochloride)

Related Biological Data

IPI-504 (Retaspimycin hydrochloride)

Related Biological Data

IPI-504 (Retaspimycin hydrochloride)

Related Biological Data

IPI-504 (Retaspimycin hydrochloride)