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Structure via PubChem · Public domain (PubChem)
umirolimus
Sign in to saveAlso known as biolimus A9
Umirolimus (INN/USAN, also called Biolimus) is an immunosuppressant, a macrocyclic lactone, a highly lipophilic derivative of sirolimus. This drug is proprietary to Biosensors International, which uses it in its own drug-eluting stents, and licenses it to partners such as Terumo.
Chemical data
- Formula
- C55H87NO14
- Molecular weight
- 986.3 g/mol
- 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
- SMILES
- CCOCCO[C@@H]1CC[C@H](C[C@H]1OC)C[C@@H](C)[C@@H]2CC(=O)[C@@H](/C=C(/[C@H]([C@H](C(=O)[C@@H](C[C@@H](/C=C/C=C/C=C(/[C@H](C[C@@H]3CC[C@H]([C@@](O3)(C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)O)C)OC)\C)C)C)OC)O)\C)C
- InChIKey
- YYSFXUWWPNHNAZ-PKJQJFMNSA-N
- XLogP
- 6.8
- Polar surface area
- 194 Ų
- H-bond donors
- 2
- H-bond acceptors
- 14
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
251 papers- Structural Aspects of mTOR Inhibitors: Search for Potential Compounds.Anti-cancer agents in medicinal chemistry · 2022
- Polymer-based or Polymer-free Stents in Patients at High Bleeding Risk.The New England journal of medicine · 2020
- Polymer-free Drug-Coated Coronary Stents in Patients at High Bleeding Risk.The New England journal of medicine · 2015
- Randomized Trial of Biolimus DCB for In-Stent Restenosis: The Primary Results of the REFORM Study.JACC. Cardiovascular interventions · 2025
- Visualization of the human coronary vasa vasorum in vivo.Circulation journal : official journal of the Japanese Circulation Society · 2015
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 985.613
Show 5 more facts
- 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
- chemical formula
- C₅₅H₈₇NO₁₄
- isomeric SMILES
- CCOCCO[C@@H]1CC[C@@H](C[C@@H](C)[C@@H]2CC(=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](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC)C[C@H]1OC
- subject has role
- immunosuppressive drug
- Commons category
- Umirolimus
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Physiological effects of umirolimus
- References
Umirolimus (INN/USAN, also called Biolimus) is an immunosuppressant, a macrocyclic lactone, a highly lipophilic derivative of sirolimus. This drug is proprietary to Biosensors International, which uses it in its own drug-eluting stents, and licenses it to partners such as Terumo.
Umirolimus inhibits T cell and smooth muscle cell proliferation, and was designed for use in drug eluting stents. This analog has a chemical modification at position 40 of the rapamycin ring. It has potent immunosuppressive properties that are similar to those of sirolimus, but the drug is more rapidly absorbed by the vessel wall, readily attaches and enters smooth muscle cell membranes causing cell cycle arrest at G0, and is comparable to sirolimus in terms of potency.
Excerpted from Wikipedia’s “umirolimus” article, available under the CC BY-SA 4.0 licence.