SM-164

ChemicalBook > CAS DataBase List > SM-164

Product Name: SM-164
CAS No.: 957135-43-2
Chemical Name: SM-164
Synonyms: SM-164;SM 164; SM164;SM-164;SM 164;SM164;SM 164 (pharmaceutical);Apoptosis,inhibit,SM164,IAP,Inhibitor,SM-164,SM 164;(3S,3'S,6S,6'S,10aS,10'aS)-N,N'-[1,4-Phenylenebis[4,1-butanediyl-1H-1,2,3-triazole-1,4-diyl[(S)-phenylmethylene]]]bis[decahydro-6-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-5-oxo-pyrrolo[1,2-a]azocine-3-carboxamide;Pyrrolo[1,2-a]azocine-3-carboxamide, N,N'-[1,4-phenylenebis[4,1-butanediyl-1H-1,2,3-triazole-1,4-diyl[(S)-phenylmethylene]]]bis[decahydro-6-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-5-oxo-, (3S,3'S,6S,6'S,10aS,10'aS)-;(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);(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);(S,3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-(1,1'-(1,4-Phenylenebis(butane-4,1-diyl))bis(1H-1,2,3-triazole-4,1-diyl))bis(phenylmethylene))bis(6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide)
CBNumber: CB92705096
Molecular Formula: C62H84N14O6
Formula Weight: 1121.45
MOL File: 957135-43-2.mol

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SM-164 Property

Density: 1.33±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO (50 mg/ml)
form: solid
pka: 12.62±0.40(Predicted)
color: White to pale-yellow
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 28632
Product name: SM-164
Packaging: 500μg
Price: $99
Updated: 2024/03/01

Cayman Chemical

Product number: 28632
Product name: SM-164
Packaging: 1mg
Price: $188
Updated: 2024/03/01

ApexBio Technology

Product number: A8815
Product name: SM-164
Packaging: 5mg
Price: $350
Updated: 2021/12/16

ApexBio Technology

Product number: A8815
Product name: SM-164
Packaging: 10mg
Price: $500
Updated: 2021/12/16

ApexBio Technology

Product number: A8815
Product name: SM-164
Packaging: 10mM(in 1mL DMSO)
Price: $630
Updated: 2021/12/16

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SM-164 Chemical Properties,Usage,Production

Description

SM-164 (957135-43-2) is a cell-permeable Smac (DIABLO) mimetic that inhibits caspase blockers XIAP, cIAP1, and cIAP2 (Ki = 36, <1, and <1.9 nM), thus inducing apoptosis.1-3 SM-164 sensitizes cancer cells to DNA damaging agents.4 It also prevents binding of Hsp70 to XIAP.5 At high concentrations, it causes lytic cell death that is neither apoptosis nor necroptosis.6

Definition

ChEBI: SM-164 is a potent cell-permeable and bivalent Smac mimetic which binds to XIAP, cIAP-1 and cIAP-2 proteins (Ki = 0.56 nM, 0.31 nM and 1.1 nM, respectively). It induces apoptosis and tumor regression in cancer xenograft models. It has a role as a radiosensitizing agent, an antineoplastic agent and an apoptosis inducer. It is a member of triazoles, a member of benzenes, a secondary carboxamide and an organic heterobicyclic compound.

target

IAP

References

Sun et al. (2007) Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP; J. Am.Chem.Soc.?129 15279 Sun et al. (2010) Nonpeptidic and potent small-molecule inhibitors of cIAP-1/2 and XIAP proteins; Med. Chem.?53 6361 Lu et al. (2008) SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP; Cancer Res.?68 9384 Chen et al. (2019) SM-164 enhances the antitumor activity of adriamycin in human U2-OS cells via downregulation of X-linked inhibitor of apoptosis protein; Med. Rep.?19 5079 Cesa et al. (2018) X-linked inhibitor of apoptosis protein (XIAP) is a client of heat shock protein 70 (Hsp70) and a biomarker of its inhibition; Biol. Chem.?293 2370 Miles et al. (2020) Smac mimetic can provoke lytic cell death that is neither apoptotic nor necroptotic; Apoptosis?25 500

SM-164 Preparation Products And Raw materials

Raw materials

Preparation Products

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SM-164 Suppliers

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957135-43-2, SM-164Related Search:

Tigecycline ML335 AZ20 NORFLUOXETINE HYDROCHLORIDE

SM-164;SM 164;SM164

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

SM 164; SM164

SM-164

(3S,3'S,6S,6'S,10aS,10'aS)-N,N'-[1,4-Phenylenebis[4,1-butanediyl-1H-1,2,3-triazole-1,4-diyl[(S)-phenylmethylene]]]bis[decahydro-6-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-5-oxo-pyrrolo[1,2-a]azocine-3-carboxamide

SM 164 (pharmaceutical)

Pyrrolo[1,2-a]azocine-3-carboxamide, N,N'-[1,4-phenylenebis[4,1-butanediyl-1H-1,2,3-triazole-1,4-diyl[(S)-phenylmethylene]]]bis[decahydro-6-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-5-oxo-, (3S,3'S,6S,6'S,10aS,10'aS)-

Apoptosis,inhibit,SM164,IAP,Inhibitor,SM-164,SM 164

(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)

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

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

957135-43-2

C62H84N14O6