LBW242

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

MedKoo CAT#: 406185

CAS#: 867324-12-7

Description: LBW242 is a Smac mimetic, and potent IAP inhibitor. LBW242 is effective against mutant FLT3 at doses that are physiologically achievable and well tolerated in vivo. LBW242 also enhances the inhibitory effects of PKC412, as well as standard chemotherapeutic agents such as doxorubicin and Ara-c, by acting in an additive-synergistic fashion against mutant FLT3-expressing cells in vitro. LBW242 also sensitizes ovarian cancer cells to the antitumor effects of TRAIL and anticancer drugs commonly used in clinic.


Price and Availability

Size
Price

10mg
Not available
100mg
Not available
1g
Ask price
Size
Price

25mg
Not available
200mg
Not available
2g
Ask price
Size
Price

50mg
Not available
500mg
Not available
5g
Ask price

LBW242 is not in stock, but 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

img

Theoretical Analysis

MedKoo Cat#: 406185
Name: LBW242
CAS#: 867324-12-7
Chemical Formula: C27H42N4O2
Exact Mass: 454.33078
Molecular Weight: 454.65
Elemental Analysis: C, 71.33; H, 9.31; N, 12.32; O, 7.04


Synonym: LBW242; LBW 242; LBW-242.

IUPAC/Chemical Name: (S)-N-((S)-1-cyclohexyl-2-oxo-2-((3aR,7aS)-6-phenethyloctahydro-1H-pyrrolo[2,3-c]pyridin-1-yl)ethyl)-2-(methylamino)propanamide

InChi Key: HCSMRSHIIKPNAK-LSAVBLLPSA-N

InChi Code: InChI=1S/C27H42N4O2/c1-20(28-2)26(32)29-25(23-11-7-4-8-12-23)27(33)31-18-15-22-14-17-30(19-24(22)31)16-13-21-9-5-3-6-10-21/h3,5-6,9-10,20,22-25,28H,4,7-8,11-19H2,1-2H3,(H,29,32)/t20-,22+,24+,25-/m0/s1

SMILES Code: C[C@H](NC)C(N[C@@H](C1CCCCC1)C(N2CC[C@]3([H])[C@@]2([H])CN(CCC4=CC=CC=C4)CC3)=O)=O


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:
>2 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


References

1: Keating J, Tsoli M, Hallahan AR, Ingram WJ, Haber M, Ziegler DS. Targeting the inhibitor of apoptosis proteins as a novel therapeutic strategy in medulloblastoma. Mol Cancer Ther. 2012 Dec;11(12):2654-63. doi: 10.1158/1535-7163.MCT-12-0352. Epub 2012 Sep 25. PubMed PMID: 23012247.

2: Petrucci E, Pasquini L, Bernabei M, Saulle E, Biffoni M, Accarpio F, Sibio S, Di Giorgio A, Di Donato V, Casorelli A, Benedetti-Panici P, Testa U. A small molecule SMAC mimic LBW242 potentiates TRAIL- and anticancer drug-mediated cell death of ovarian cancer cells. PLoS One. 2012;7(4):e35073. doi: 10.1371/journal.pone.0035073. Epub 2012 Apr 25. PubMed PMID: 22558117; PubMed Central PMCID: PMC3338831.

3: Eschenburg G, Eggert A, Schramm A, Lode HN, Hundsdoerfer P. Smac mimetic LBW242 sensitizes XIAP-overexpressing neuroblastoma cells for TNF-α-independent apoptosis. Cancer Res. 2012 May 15;72(10):2645-56. doi: 10.1158/0008-5472.CAN-11-4072. Epub 2012 Apr 9. PubMed PMID: 22491673.

4: Ziegler DS, Keating J, Kesari S, Fast EM, Zawel L, Ramakrishna N, Barnes J, Kieran MW, Veldhuijzen van Zanten SE, Kung AL. A small-molecule IAP inhibitor overcomes resistance to cytotoxic therapies in malignant gliomas in vitro and in vivo. Neuro Oncol. 2011 Aug;13(8):820-9. doi: 10.1093/neuonc/nor066. Epub 2011 Jul 1. PubMed PMID: 21724651; PubMed Central PMCID: PMC3145470.

5: Xu Y, Zhou L, Huang J, Liu F, Yu J, Zhan Q, Zhang L, Zhao X. Role of Smac in determining the chemotherapeutic response of esophageal squamous cell carcinoma. Clin Cancer Res. 2011 Aug 15;17(16):5412-22. doi: 10.1158/1078-0432.CCR-11-0426. Epub 2011 Jun 15. PubMed PMID: 21676925.

6: Hundsdoerfer P, Dietrich I, Schmelz K, Eckert C, Henze G. XIAP expression is post-transcriptionally upregulated in childhood ALL and is associated with glucocorticoid response in T-cell ALL. Pediatr Blood Cancer. 2010 Aug;55(2):260-6. doi: 10.1002/pbc.22541. PubMed PMID: 20582956.

7: Weber A, Kirejczyk Z, Besch R, Potthoff S, Leverkus M, Häcker G. Proapoptotic signalling through Toll-like receptor-3 involves TRIF-dependent activation of caspase-8 and is under the control of inhibitor of apoptosis proteins in melanoma cells. Cell Death Differ. 2010 Jun;17(6):942-51. doi: 10.1038/cdd.2009.190. Epub 2009 Dec 18. PubMed PMID: 20019748.

8: Ziegler DS, Wright RD, Kesari S, Lemieux ME, Tran MA, Jain M, Zawel L, Kung AL. Resistance of human glioblastoma multiforme cells to growth factor inhibitors is overcome by blockade of inhibitor of apoptosis proteins. J Clin Invest. 2008 Sep;118(9):3109-22. doi: 10.1172/JCI34120. PubMed PMID: 18677408; PubMed Central PMCID: PMC2491457.

9: Gaither A, Porter D, Yao Y, Borawski J, Yang G, Donovan J, Sage D, Slisz J, Tran M, Straub C, Ramsey T, Iourgenko V, Huang A, Chen Y, Schlegel R, Labow M, Fawell S, Sellers WR, Zawel L. A Smac mimetic rescue screen reveals roles for inhibitor of apoptosis proteins in tumor necrosis factor-alpha signaling. Cancer Res. 2007 Dec 15;67(24):11493-8. PubMed PMID: 18089776.

10: Weisberg E, Kung AL, Wright RD, Moreno D, Catley L, Ray A, Zawel L, Tran M, Cools J, Gilliland G, Mitsiades C, McMillin DW, Jiang J, Hall-Meyers E, Griffin JD. Potentiation of antileukemic therapies by Smac mimetic, LBW242: effects on mutant FLT3-expressing cells. Mol Cancer Ther. 2007 Jul;6(7):1951-61. PubMed PMID: 17620426.

11: Chauhan D, Neri P, Velankar M, Podar K, Hideshima T, Fulciniti M, Tassone P, Raje N, Mitsiades C, Mitsiades N, Richardson P, Zawel L, Tran M, Munshi N, Anderson KC. Targeting mitochondrial factor Smac/DIABLO as therapy for multiple myeloma (MM). Blood. 2007 Feb 1;109(3):1220-7. Epub 2006 Oct 10. PubMed PMID: 17032924; PubMed Central PMCID: PMC1785138.