BMS-536924

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200521

CAS#: 468740-43-4

Description: BMS-536924 is a potent small molecule inhibitor of IGF-IR, which shows antitumor activity in multiple tumor models, including sarcoma.


Price and Availability

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BMS-536924, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200521
Name: BMS-536924
CAS#: 468740-43-4
Chemical Formula: C25H26ClN5O3
Exact Mass: 479.17242
Molecular Weight: 479.96
Elemental Analysis: C, 62.56; H, 5.46; Cl, 7.39; N, 14.59; O, 10.00


Synonym: BMS536924; BMS-536924; BMS 536924.

IUPAC/Chemical Name: (S)-4-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)-3-(4-methyl-6-morpholino-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one

InChi Key: ZWVZORIKUNOTCS-OAQYLSRUSA-N

InChi Code: InChI=1S/C25H26ClN5O3/c1-15-11-18(31-7-9-34-10-8-31)13-20-23(15)30-24(29-20)22-19(5-6-27-25(22)33)28-14-21(32)16-3-2-4-17(26)12-16/h2-6,11-13,21,32H,7-10,14H2,1H3,(H,29,30)(H2,27,28,33)/t21-/m1/s1

SMILES Code: O=C1C(C2=NC3=C(C)C=C(N4CCOCC4)C=C3N2)=C(NC[C@H](C5=CC=CC(Cl)=C5)O)C=CN1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

BMS-535924 is a potent inhibitor of the IGF-1 receptor in vitro  (IC50 = 100 nM). BMS-536924 has been shown to inhibit the catalytic activity of IGF-1R and its down stream signaling components such as Akt and MAPK in cells; it also inhibits proliferation in a wide variety of human cancer cell lines including, colon, breast, lung, pancreas, prostate, sarcoma and multiple myeloma. In vivo, BMS-536924 inhibits tumor growth in an IGF-1R-dependent tumor model (IGF-1R Sal) as well as in a broad range of human tumor xenografts.
 


References

1: Velaparthi U, Saulnier MG, Wittman MD, Liu P, Frennesson DB, Zimmermann K, Carboni JM, Gottardis M, Li A, Greer A, Clarke W, Yang Z, Menard K, Lee FY, Trainor G, Vyas D. Insulin-like growth factor-1 receptor (IGF-1R) kinase inhibitors: SAR of a series of 3-[6-(4-substituted-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-1H-pyridine-2- one. Bioorg Med Chem Lett. 2010 May 15;20(10):3182-5. Epub 2010 Mar 27. PubMed PMID: 20399649.

2: Novosyadlyy R, Lann DE, Vijayakumar A, Rowzee A, Lazzarino DA, Fierz Y, Carboni JM, Gottardis MM, Pennisi PA, Molinolo AA, Kurshan N, Mejia W, Santopietro S, Yakar S, Wood TL, LeRoith D. Insulin-mediated acceleration of breast cancer development and progression in a nonobese model of type 2 diabetes. Cancer Res. 2010 Jan 15;70(2):741-51. Epub 2010 Jan 12. PubMed PMID: 20068149.

3: Wahner Hendrickson AE, Haluska P, Schneider PA, Loegering DA, Peterson KL, Attar R, Smith BD, Erlichman C, Gottardis M, Karp JE, Carboni JM, Kaufmann SH. Expression of insulin receptor isoform A and insulin-like growth factor-1 receptor in human acute myelogenous leukemia: effect of the dual-receptor inhibitor BMS-536924 in vitro. Cancer Res. 2009 Oct 1;69(19):7635-43. Epub 2009 Sep 29. PubMed PMID: 19789352; PubMed Central PMCID: PMC2762752.

4: Beauchamp MC, Knafo A, Yasmeen A, Carboni JM, Gottardis MM, Pollak MN, Gotlieb WH. BMS-536924 sensitizes human epithelial ovarian cancer cells to the PARP inhibitor, 3-aminobenzamide. Gynecol Oncol. 2009 Nov;115(2):193-8. Epub 2009 Aug 21. PubMed PMID: 19699512.

5: Avnet S, Sciacca L, Salerno M, Gancitano G, Cassarino MF, Longhi A, Zakikhani M, Carboni JM, Gottardis M, Giunti A, Pollak M, Vigneri R, Baldini N. Insulin receptor isoform A and insulin-like growth factor II as additional treatment targets in human osteosarcoma. Cancer Res. 2009 Mar 15;69(6):2443-52. Epub 2009 Mar 3. PubMed PMID: 19258511.

6: Xu Y, Wang GS, Sun W, Yang XH, Xu LB. [Progress in the studies on small molecule IGF-1R inhibitors]. Yao Xue Xue Bao. 2008 Oct;43(10):979-84. Review. Chinese. PubMed PMID: 19127859.

7: Litzenburger BC, Kim HJ, Kuiatse I, Carboni JM, Attar RM, Gottardis MM, Fairchild CR, Lee AV. BMS-536924 reverses IGF-IR-induced transformation of mammary epithelial cells and causes growth inhibition and polarization of MCF7 cells. Clin Cancer Res. 2009 Jan 1;15(1):226-37. PubMed PMID: 19118050; PubMed Central PMCID: PMC2819349.

8: Huang F, Greer A, Hurlburt W, Han X, Hafezi R, Wittenberg GM, Reeves K, Chen J, Robinson D, Li A, Lee FY, Gottardis MM, Clark E, Helman L, Attar RM, Dongre A, Carboni JM. The mechanisms of differential sensitivity to an insulin-like growth factor-1 receptor inhibitor (BMS-536924) and rationale for combining with EGFR/HER2 inhibitors. Cancer Res. 2009 Jan 1;69(1):161-70. PubMed PMID: 19117999.

9: Law JH, Habibi G, Hu K, Masoudi H, Wang MY, Stratford AL, Park E, Gee JM, Finlay P, Jones HE, Nicholson RI, Carboni J, Gottardis M, Pollak M, Dunn SE. Phosphorylated insulin-like growth factor-i/insulin receptor is present in all breast cancer subtypes and is related to poor survival. Cancer Res. 2008 Dec 15;68(24):10238-46. PubMed PMID: 19074892.

10: Haluska P, Carboni JM, TenEyck C, Attar RM, Hou X, Yu C, Sagar M, Wong TW, Gottardis MM, Erlichman C. HER receptor signaling confers resistance to the insulin-like growth factor-I receptor inhibitor, BMS-536924. Mol Cancer Ther. 2008 Sep;7(9):2589-98. Epub 2008 Sep 2. PubMed PMID: 18765823; PubMed Central PMCID: PMC2614316.