SM-164
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MedKoo CAT#: 407187

CAS#: 957135-43-2

Description: SM-164 is a potent cell-permeable and bivalent Smac mimetic which bind to a XIAP protein and binds to cIAP-1 and cIAP-2 proteins. It is developed as an anticancer agent. It plays its antitumor roles through inducing degradation of cellular inhibitor of apoptosis protein (cIAP)-1/2, antagonizing X-linked inhibitor of apoptosis protein (XIAP) and inducing TNFα–dependent apoptosis in tumor cells. SM-164 is a bivalent mimetic containing two SM-122 analogues. It binds to cIAP-1 protein containing bothBIR2 and BIR3 domains, cIAP-2 BIR3 protein and XIAP protein containing both BIR2 and BIR3 domains.


Chemical Structure

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SM-164
CAS# 957135-43-2

Theoretical Analysis

MedKoo Cat#: 407187
Name: SM-164
CAS#: 957135-43-2
Chemical Formula: C62H84N14O6
Exact Mass: 1120.66983
Molecular Weight: 1121.45
Elemental Analysis: C, 66.40; H, 7.55; N, 17.49; O, 8.56

Price and Availability

Size Price Availability Quantity
5.0mg USD 550.0 2 Weeks
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Synonym: SM 164; SM164; SM-164.

IUPAC/Chemical Name: (3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-((1,4-phenylenebis(butane-4,1-diyl))bis(1H-1,2,3-triazole-1,4-diyl))bis(phenylmethylene))bis(6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide)

InChi Key: LGYDZXNSSLRFJS-IOQQVAQYSA-N

InChi Code: InChI=1S/C62H84N14O6/c1-41(63-3)57(77)65-49-27-13-11-25-47-33-35-53(75(47)61(49)81)59(79)67-55(45-21-7-5-8-22-45)51-39-73(71-69-51)37-17-15-19-43-29-31-44(32-30-43)20-16-18-38-74-40-52(70-72-74)56(46-23-9-6-10-24-46)68-60(80)54-36-34-48-26-12-14-28-50(62(82)76(48)54)66-58(78)42(2)64-4/h5-10,21-24,29-32,39-42,47-50,53-56,63-64H,11-20,25-28,33-38H2,1-4H3,(H,65,77)(H,66,78)(H,67,79)(H,68,80)/t41-,42-,47-,48-,49-,50-,53-,54-,55-,56-/m0/s1

SMILES Code: O=C1N2[C@@](CC[C@H]2C(N[C@H](C3=CN(CCCCC4=CC=C(CCCCN5N=NC([C@@H](NC([C@H](CC[C@@]6(CCCC7)[H])N6C([C@H]7NC([C@@H](NC)C)=O)=O)=O)C8=CC=CC=C8)=C5)C=C4)N=N3)C9=CC=CC=C9)=O)([H])CCCC[C@@H]1NC([C@H](C)NC)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 1121.45 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

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1: Kocab AJ, Veloso A, Paulsen MT, Ljungman M, Duckett CS. Effects of physiological and synthetic IAP antagonism on c-IAP-dependent signaling. Oncogene. 2015 Oct;34(43):5472-81. doi: 10.1038/onc.2015.3. Epub 2015 Feb 9. PubMed PMID: 25659587; PubMed Central PMCID: PMC4530109.

2: Raulf N, El-Attar R, Kulms D, Lecis D, Delia D, Walczak H, Papenfuss K, Odell E, Tavassoli M. Differential response of head and neck cancer cell lines to TRAIL or Smac mimetics is associated with the cellular levels and activity of caspase-8 and caspase-10. Br J Cancer. 2014 Nov 11;111(10):1955-64. doi: 10.1038/bjc.2014.521. Epub 2014 Oct 14. PubMed PMID: 25314064; PubMed Central PMCID: PMC4229641.

3: Wu MS, Wang GF, Zhao ZQ, Liang Y, Wang HB, Wu MY, Min P, Chen LZ, Feng QS, Bei JX, Zeng YX, Yang D. Smac mimetics in combination with TRAIL selectively target cancer stem cells in nasopharyngeal carcinoma. Mol Cancer Ther. 2013 Sep;12(9):1728-37. doi: 10.1158/1535-7163.MCT-13-0017. Epub 2013 May 22. PubMed PMID: 23699656.

4: Zhang S, Li G, Zhao Y, Liu G, Wang Y, Ma X, Li D, Wu Y, Lu J. Smac mimetic SM-164 potentiates APO2L/TRAIL- and doxorubicin-mediated anticancer activity in human hepatocellular carcinoma cells. PLoS One. 2012;7(12):e51461. doi: 10.1371/journal.pone.0051461. Epub 2012 Dec 11. PubMed PMID: 23240027; PubMed Central PMCID: PMC3519882.

5: Zhou B, Zhang J, Chen G, You L, Zhang TP, Zhao YP. Therapy of Smac mimetic SM-164 in combination with gemcitabine for pancreatic cancer. Cancer Lett. 2013 Feb 1;329(1):118-24. doi: 10.1016/j.canlet.2012.10.039. Epub 2012 Nov 8. PubMed PMID: 23142291.

6: McComb S, Cheung HH, Korneluk RG, Wang S, Krishnan L, Sad S. cIAP1 and cIAP2 limit macrophage necroptosis by inhibiting Rip1 and Rip3 activation. Cell Death Differ. 2012 Nov;19(11):1791-801. doi: 10.1038/cdd.2012.59. Epub 2012 May 11. PubMed PMID: 22576661; PubMed Central PMCID: PMC3469059.

7: Bai L, McEachern D, Yang CY, Lu J, Sun H, Wang S. LRIG1 modulates cancer cell sensitivity to Smac mimetics by regulating TNFα expression and receptor tyrosine kinase signaling. Cancer Res. 2012 Mar 1;72(5):1229-38. doi: 10.1158/0008-5472.CAN-11-2428. Epub 2012 Jan 12. PubMed PMID: 22241084; PubMed Central PMCID: PMC3294058.

8: Yang D, Zhao Y, Li AY, Wang S, Wang G, Sun Y. Smac-mimetic compound SM-164 induces radiosensitization in breast cancer cells through activation of caspases and induction of apoptosis. Breast Cancer Res Treat. 2012 May;133(1):189-99. doi: 10.1007/s10549-011-1752-3. Epub 2011 Sep 7. PubMed PMID: 21901386.

9: Lu J, McEachern D, Sun H, Bai L, Peng Y, Qiu S, Miller R, Liao J, Yi H, Liu M, Bellail A, Hao C, Sun SY, Ting AT, Wang S. Therapeutic potential and molecular mechanism of a novel, potent, nonpeptide, Smac mimetic SM-164 in combination with TRAIL for cancer treatment. Mol Cancer Ther. 2011 May;10(5):902-14. doi: 10.1158/1535-7163.MCT-10-0864. Epub 2011 Mar 3. PubMed PMID: 21372226; PubMed Central PMCID: PMC3091962.

10: Yang J, McEachern D, Li W, Davis MA, Li H, Morgan MA, Bai L, Sebolt JT, Sun H, Lawrence TS, Wang S, Sun Y. Radiosensitization of head and neck squamous cell carcinoma by a SMAC-mimetic compound, SM-164, requires activation of caspases. Mol Cancer Ther. 2011 Apr;10(4):658-69. doi: 10.1158/1535-7163.MCT-10-0643. Epub 2011 Jan 31. PubMed PMID: 21282353; PubMed Central PMCID: PMC3073022.

SM-164

5.0mg / USD 550.0