Umirolimus
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04310 |
| CAS | 851536-75-9 |
| Molecular Weight | 986.28 |
| Molecular Formula | C55H87NO14 |
| Purity | >95% by HPLC |
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Description
A semi-synthetic macrocyclic lactone prepared from rapamycin by selective alkylation of the 42-hydroxy group. It is one of the most hydrophobic tacrolimus analogues. It binds to the cytosolic FK-binding protein 12 (FKBP12) to inhibit the mammalian target of rapamycin (mTOR) pathway.
Specification
| Synonyms | Biolimus; Biolimus A9; TRM 986; 42-O-(2-Ethoxyethyl)rapamycin |
| Storage | Store at -20°C |
| IUPAC Name | (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-12-[(2R)-1-[(1S,3R,4R)-4-(2-ethoxyethoxy)-3-methoxycyclohexyl]propan-2-yl]-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone |
| Canonical SMILES | CCOCCOC1CCC(CC1OC)CC(C)C2CC(=O)C(C=C(C(C(C(=O)C(CC(C=CC=CC=C(C(CC3CCC(C(O3)(C(=O)C(=O)N4CCCCC4C(=O)O2)O)C)OC)C)C)C)OC)O)C)C |
| InChI | InChI=1S/C55H87NO14/c1-12-67-26-27-68-45-24-22-41(31-48(45)65-10)30-37(5)47-33-44(57)36(4)29-39(7)50(59)51(66-11)49(58)38(6)28-34(2)18-14-13-15-19-35(3)46(64-9)32-42-23-21-40(8)55(63,70-42)52(60)53(61)56-25-17-16-20-43(56)54(62)69-47/h13-15,18-19,29,34,36-38,40-43,45-48,50-51,59,63H,12,16-17,20-28,30-33H2,1-11H3/b15-13+,18-14+,35-19+,39-29+/t34-,36-,37-,38-,40-,41+,42+,43+,45-,46+,47+,48-,50-,51+,55-/m1/s1 |
| InChI Key | YYSFXUWWPNHNAZ-PKJQJFMNSA-N |
| Source | Streptomyces hygroscopicus |
Properties
| Appearance | White Solid |
| Boiling Point | 991.0±75.0°C (Predicted) |
| Density | 1.15±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. The Nobori biolimus-eluting stent: update of available evidence
Raffaele Piccolo, Annamaria Nicolino, Gian Battista Danzi Expert Rev Med Devices . 2014 May;11(3):275-82. doi: 10.1586/17434440.2014.894458.
Despite first-generation drug-eluting stents (DES) dramatically reduced the need for repeat revascularization in patients undergoing percutaneous coronary intervention, their use was associated with an increased risk of thrombotic events at long-term follow-up. The Nobori biolimus-eluting stent (BES) is a second-generation DES with a biodegradable poly-lactic acid polymer. During the last few years, several randomized trials have compared the Nobori BES with other DES, making this device the most investigated biodegradable DES. In this article, we reviewed current available data about Nobori BES from pharmacokinetic and observational studies to randomized clinical trials.
2. Polymer-based or Polymer-free Stents in Patients at High Bleeding Risk
Stephen G Worthley, Hyo-Soo Kim, Ajay J Kirtane, Ivana Jankovic, Elvin Kedhi, Alexandre Abizaid, Kamaraj Selvaraj, ONYX ONE Investigators, Azeem Latib, Martin Hudec, Adel Aminian, Adrian Wlodarczak, Gregg W Stone, Charles Tie, Daniel I Simon, Eduardo Pinar, Matthew J Price, Lisa Bousquette, Stephan Windecker, Roxana Mehran, Petra Poliacikova, Franco Fabbiocchi, Steven O Marx, Darren Mylotte, Azfar Zaman, David E Kandzari, Ivo Petrov, Seung-Ho Hur, Minglei Liu, Sandeep Brar, Sanjeevan Pasupati, A Kahar Bin Abdul Ghapar, Raul Moreno N Engl J Med . 2020 Mar 26;382(13):1208-1218. doi: 10.1056/NEJMoa1910021.
Background:Polymer-free drug-coated stents provide superior clinical outcomes to bare-metal stents in patients at high bleeding risk who undergo percutaneous coronary intervention (PCI) and are treated with 1 month of dual antiplatelet therapy. Data on the use of polymer-based drug-eluting stents, as compared with polymer-free drug-coated stents, in such patients are limited.Methods:In an international, randomized, single-blind trial, we compared polymer-based zotarolimus-eluting stents with polymer-free umirolimus-coated stents in patients at high bleeding risk. After PCI, patients were treated with 1 month of dual antiplatelet therapy, followed by single antiplatelet therapy. The primary outcome was a safety composite of death from cardiac causes, myocardial infarction, or stent thrombosis at 1 year. The principal secondary outcome was target-lesion failure, an effectiveness composite of death from cardiac causes, target-vessel myocardial infarction, or clinically indicated target-lesion revascularization. Both outcomes were powered for noninferiority.Results:A total of 1996 patients at high bleeding risk were randomly assigned in a 1:1 ratio to receive zotarolimus-eluting stents (1003 patients) or polymer-free drug-coated stents (993 patients). At 1 year, the primary outcome was observed in 169 of 988 patients (17.1%) in the zotarolimus-eluting stent group and in 164 of 969 (16.9%) in the polymer-free drug-coated stent group (risk difference, 0.2 percentage points; upper boundary of the one-sided 97.5% confidence interval [CI], 3.5; noninferiority margin, 4.1; P = 0.01 for noninferiority). The principal secondary outcome was observed in 174 patients (17.6%) in the zotarolimus-eluting stent group and in 169 (17.4%) in the polymer-free drug-coated stent group (risk difference, 0.2 percentage points; upper boundary of the one-sided 97.5% CI, 3.5; noninferiority margin, 4.4; P = 0.007 for noninferiority).Conclusions:Among patients at high bleeding risk who received 1 month of dual antiplatelet therapy after PCI, use of polymer-based zotarolimus-eluting stents was noninferior to use of polymer-free drug-coated stents with regard to safety and effectiveness composite outcomes. (Funded by Medtronic; ONYX ONE ClinicalTrials.gov number,NCT03344653.).
3. Polymer-free Drug-Coated Coronary Stents in Patients at High Bleeding Risk
Robaayah Zambahari, Gert Richardt, Christophe Dubois, Agustin Albarran, Jacques Berland, Jonathan Byrne, Tiziano Moccetti, Simon Redwood, Philip Lurz, Samantha Greene, Janusz Lipiecki, Philippe Garot, Evald H Christiansen, John Gregson, Andres Iñiguez, Shmuel Banai, Haim Danenberg, Eric Van Belle, Luc Maillard, Ian T Meredith, Mariano Valdes-Chavarri, Alexandre Abizaid, Andrejs Erglis, Antonio Bartorelli, Paul Ong, Simon James Walsh, Ian B A Menown, Stuart J Pocock, Marc Bedossa, Irene Lang, Lim Soo Teik, Mark De Belder, Eric Maupas, Franz-Josef Neumann, Oliver Gaemperli, David Foley, Jean Fajadet, Mohamed Abdellaoui, Maurizio Tespili, Marcel Gosselink, Marie-Claude Morice, LEADERS FREE Investigators, Alaide Chieffo, Keith Oldroyd, Antonio Colombo, Thomas Engström, Franz Eberli, Silvio Klugmann, Werner Jung, Christoph Naber, Hans-Peter Stoll, Corrado Tamburino, David Hildick-Smith, Roberto Violini, Eric Eeckhout, Azfar Zaman, Damras Tresukosol, Didier Carrié, Philippe Brunel, Marc Eric Moulichon, Stefan Verheye, Robayaah Zambahari, Christian Spaulding, Chan Koo Hui, Sonny Dandona, Piers Clifford, Philip Strike, Rune Wiseth, Stephen Lee, Darren Walters, Ran Kornowski, Thomas Hovasse, Ever Grech, Ian Meredith, Luc Bilodeau, Philip Urban, Florian Krackhardt, Raul Moreno, Suneel Talwar N Engl J Med . 2015 Nov 19;373(21):2038-47. doi: 10.1056/NEJMoa1503943.
Background:Patients at high risk for bleeding who undergo percutaneous coronary intervention (PCI) often receive bare-metal stents followed by 1 month of dual antiplatelet therapy. We studied a polymer-free and carrier-free drug-coated stent that transfers umirolimus (also known as biolimus A9), a highly lipophilic sirolimus analogue, into the vessel wall over a period of 1 month.Methods:In a randomized, double-blind trial, we compared the drug-coated stent with a very similar bare-metal stent in patients with a high risk of bleeding who underwent PCI. All patients received 1 month of dual antiplatelet therapy. The primary safety end point, tested for both noninferiority and superiority, was a composite of cardiac death, myocardial infarction, or stent thrombosis. The primary efficacy end point was clinically driven target-lesion revascularization.Results:We enrolled 2466 patients. At 390 days, the primary safety end point had occurred in 112 patients (9.4%) in the drug-coated-stent group and in 154 patients (12.9%) in the bare-metal-stent group (risk difference, -3.6 percentage points; 95% confidence interval [CI], -6.1 to -1.0; hazard ratio, 0.71; 95% CI, 0.56 to 0.91; P<0.001 for noninferiority and P=0.005 for superiority). During the same time period, clinically driven target-lesion revascularization was needed in 59 patients (5.1%) in the drug-coated-stent group and in 113 patients (9.8%) in the bare-metal-stent group (risk difference, -4.8 percentage points; 95% CI, -6.9 to -2.6; hazard ratio, 0.50; 95% CI, 0.37 to 0.69; P<0.001).Conclusions:Among patients at high risk for bleeding who underwent PCI, a polymer-free umirolimus-coated stent was superior to a bare-metal stent with respect to the primary safety and efficacy end points when used with a 1-month course of dual antiplatelet therapy. (Funded by Biosensors Europe; LEADERS FREE ClinicalTrials.gov number,NCT01623180.).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
