Stereochemistry | ABSOLUTE |
Molecular Formula | C52H79N5O12 |
Molecular Weight | 966.21 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@H](C)[C@@](O)(O1)C(=O)C(=O)N3CCCC[C@@]3([H])C(=O)O[C@@]([H])(CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C2)OC)[C@H](C)C[C@@H]4CC[C@@H]([C@@H](C4)OC)N5C=NN=N5
InChI
InChIKey=CGTADGCBEXYWNE-JUKNQOCSSA-N
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
Molecular Formula | C52H79N5O12 |
Molecular Weight | 966.21 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Zotarolimus (ABT-578) is an immunosuppressant. It is a semi-synthetic derivative of rapamycin. It was designed for use in stents with phosphorylcholine as a carrier. Coronary stents reduce early complications and improve late clinical outcomes in patients needing interventional cardiology. Medtronic are using zotarolimus as the anti-proliferative agent in the polymer coating of their Endeavor and Resolute products. Zotarolimus was developed by Abbott Laboratories as the first cytostatic agent to be used solely for delivery from drug-eluting stents to prevent restenosis. The mechanism (or mechanisms) by which the Endeavor Zotarolimus-Eluting Coronary Stent System affects neointimal production as seen in clinical studies has not been established conclusively. In vitro, zotarolimus inhibited growth factor-induced proliferation of human coronary artery smooth muscle cells and also demonstrated binding affinity with FKBP 12 (binding protein). The suggested mechanism of action of zotarolimus is to bind to FKBP 12, leading to the formation of a trimeric complex with the protein kinase mTOR (mammalian target of rapamycin), inhibiting its activity. Inhibition of mTOR activity leads to inhibition of cell cycle progression from the GI to the S phase.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
The drug component of the Endeavor Zotarolimus-Eluting Coronary Stent System consists of zotarolimus (the active ingredient) and Phosphorylcholine (PC) polymer (the inactive ingredient).
The Endeavor stent contains 10 ug zotarolimus per millimeter of stent length for all diameters. Because an identical dose (l0 ug/mm zotarolimus per mm stent length) is used for the entire Endeavor 2.5 mm - 3.5 mm diameter range, the total drug per stent is a function of stent length, irrespective of stent diameter.
Route of Administration:
Other