A rapamycin derivative
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Umirolimus

Item No. 23585

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
42-O-(2-ethoxyethyl)-rapamycin
CAS Number
851536-75-9
Molecular Formula
C55H87NO14
Formula Weight
986.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C([C@]1([H])CCCCN1C(C([C@@]2(O)[C@H](C)CC[C@](C[C@H](OC)/C(C)=C/C=C/C=C/[C@H](C3)C)([H])O2)=O)=O)O[C@](CC([C@H](C)/C=C(C)/[C@@H](O)[C@@H](OC)C([C@@H]3C)=O)=O)([H])[C@H](C)C[C@@H]4CC[C@@H](OCCOCC)[C@H](OC)C4
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $129

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    5 mg

    $510

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    Product Description

    Umirolimus is a semisynthetic macrocyclic lactone and a derivative of rapamycin (Item No. 13346) that has immunosuppressive and anti-inflammatory effects.1 It halts the cell cycle at the G1 phase through an IL-2/mTOR-mediated pathway and inhibits proliferation of human smooth muscle cells. In a porcine overstretch model, coronary stents containing umirolimus for localized delivery to the vessel wall reduced stenosis by 50% and led to less thickening of the vessel wall than a bare metal stent. Rapamycin, and likely its derivatives, binds to the cytosolic FK-binding protein 12 (FKBP12) to inhibit the mammalian target of rapamycin (mTOR) pathway. Formulations containing umirolimus have been used in coronary stents for localized delivery to the vessel wall.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Grube, E., and Buellesfeld, L. BioMatrix® Biolimus A9®-eluting coronary stent: A next-generation drug-eluting stent for coronary artery disease. Expert Rev. Med. Devices 3(6), 731-741 (2006).