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SML2196

Sigma-Aldrich

Zotarolimus

≥95% (HPLC)

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Synonym(s):
(42S)-42-Deoxy-42-(1H-tetrazol-1-yl)rapamycin, ABT-578
Empirical Formula (Hill Notation):
C52H79N5O12
CAS Number:
221877-54-9
Molecular Weight:
966.21
MDL number:
MFCD09752954
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

C[C@H](CC[C@@H](C[C@H](OC)/C(C)=C/C=C/C=C/[C@H](C[C@H](C([C@H](OC)[C@@H](/C(C)=C/[C@@H](C)C1=O)O)=O)C)C)O2)[C@]2(O)C(C(N3CCCC[C@H]3C(O[C@H]([C@H](C)C[C@@H]4CC[C@H](N5N=NN=C5)[C@H](OC)C4)C1)=O)=O)=O

InChI

1S/C52H79N5O12/c1-31-16-12-11-13-17-32(2)43(65-8)28-39-21-19-37(7)52(64,69-39)49(61)50(62)56-23-15-14-18-41(56)51(63)68-44(34(4)26-38-20-22-40(45(27-38)66-9)57-30-53-54-55-57)29-42(58)33(3)25-36(6)47(60)48(67-10)46(59)35(5)24-31/h11-13,16-17,25,30-31,33-35,37-41,43-45,47-48,60,64H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,32-17+,36-25+/t31-,33-,34-,35-,37-,38+,39+,40+,41+,43+,44+,45-,47-,48+,52-/m1/s1

InChI key

CGTADGCBEXYWNE-JUKNQOCSSA-N

Biochem/physiol Actions

Zotarolimus (ABT-578) is a semi-synthetic rapamycin analog with immunosuppressant and anti-proliferative activity. It binds to the FKBP12 binding protein, which subsequently binds to the mammalian target of rapamycin (mTOR) causing cell cycle arrest in the G1 phase. Zotarolimus was designed to be used for delivery from drug-eluting coronary stents to prevent restenosis.
Zotarolimus is a second generation Drug Eluting Stent (DES).

WGK

WGK 3

Certificates of Analysis (COA)

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Keiichiro Miura et al.
Cardiovascular revascularization medicine : including molecular interventions, 16(6), 344-347 (2015-08-09)
Late and very late stent thrombosis after drug-eluting stent implantation is a major concern. The present study evaluated difference in the effects of sirolimus, paclitaxel and zotarolimus on endothelial cells. Mouse endothelial cells were seeded in a 6-well plate. Cells
Yuji Nishimoto et al.
Journal of cardiology, 70(3), 297-302 (2016-12-31)
First-generation drug-eluting stents (DES) have reduced short-term stent failure as compared to bare-metal stents due to the inhibition of neointima hyperplasia, but instead increased the risk of very-late stent failure. Although better outcomes have been reported for second-generation DES than
Zotarolimus-eluting versus bare-metal stents in uncertain drug-eluting stent candidates
Valgimigli M, et al.
Journal of the American College of Cardiology, 65(8), 805-815 (2015)
Fabrizio D'Ascenzo et al.
European heart journal, 38(42), 3160-3172 (2017-10-12)
The differential impact on ischaemic and bleeding events of the type of drug-eluting stent [durable polymer stents [DES] vs. biodegradable polymer stents vs. bioresorbable scaffolds (BRS)] and length of dual antiplatelet therapy (DAPT) remains to be defined. Randomized controlled trials

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