MedKoo Cat#: 406185 | Name: LBW242

Description:

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

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.

Chemical Structure

LBW242
LBW242
CAS#867324-12-7

Theoretical Analysis

MedKoo Cat#: 406185

Name: LBW242

CAS#: 867324-12-7

Chemical Formula: C27H42N4O2

Exact Mass: 454.3308

Molecular Weight: 454.65

Elemental Analysis: C, 71.33; H, 9.31; N, 12.32; O, 7.04

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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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
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 454.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.