Zotarolimus

Base Information

• Chemical Name: Zotarolimus
• CAS No.: 221877-54-9
• Deprecated CAS: 916135-04-1
• Molecular Formula: C52H79 N5 O12
• Molecular Weight: 966.21
• Hs Code.: 29349990
• UNII: H4GXR80IZE
• DSSTox Substance ID: DTXSID50873387
• Wikipedia: Zotarolimus
• Wikidata: Q15410168
• NCI Thesaurus Code: C82294
• Pharos Ligand ID: GU8P4TKXMSQJ
• ChEMBL ID: CHEMBL219410
• Mol file: 221877-54-9.mol

Synonyms:ABT 578;ABT-578;ABT578;zotarilumus;zotarolimus

Chemical Property of Zotarolimus

Chemical Property:

• Melting Point: 100-105°C
• Boiling Point: 1016.2°Cat760mmHg
• PKA: 10.40±0.70(Predicted)
• Flash Point: 568.4°C
• PSA: 218.80000
• Density: 1.25g/cm³
• LogP: 5.98540
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO, Methanol (Slightly)
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 7
• Exact Mass: 965.57252297
• Heavy Atom Count: 69
• Complexity: 1890

Purity/Quality:

99.8% ^*data from raw suppliers

Zotarolimus ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)N5C=NN=N5)C)C)O)OC)C)C)C)OC
• Isomeric SMILES: C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@@H]([C@@H](C4)OC)N5C=NN=N5)C)/C)O)OC)C)C)/C)OC
• Description: Zotarolimus is a macrocyclic lactone immunosuppressant and a derivative of rapamycin . It binds to FKBP prolyl isomerase 1A (FKBP12; IC50 = 2.57 nM) and inhibits proliferation of human peripheral blood mononuclear cells (PBMCs), rat splenocytes, and human coronary artery smooth muscle cells (IC50s = 7, 1,337, and 0.8 nM, respectively). Zotarolimus has immunosuppressive activity in a one-way mixed lymphocyte reaction using human or rat lymphocytes (IC50s = 1.2 and 1,465 nM, respectively). It also reduces symptom severity in a rat model of experimental autoimmune encephalomyelitis (EAE; ED50 = 1.17 mg/kg per day) and delays cardiac allograft rejection in rats (ED50 = 3.71 mg/kg per day). Zotarolimus inhibits neointimal formation and reduces stenosis in pig coronary arteries when applied at 10 μg/mm to stainless steel balloon expandable stents with phosphorylcholine in a model of restenosis. Formulations containing zotarolimus have been used in drug-eluting stents in the prevention of restenosis following stent placement.
• Uses: Zotarolimus is a semi-synthetic macrocyclic lactone prepared from rapamycin by preparation of the 42-triflate ester, followed by displacement with tetrazole and purification of the two isomeric products. This structural change affords a less bioavailable product, a preferred profile for some applications. Like all tacrolimus analogues, zotarolimus binds to a receptor protein (FKBP12). The complex then binds to preventing it from interacting with target proteins. Zotarolimus is extensively cited in the literature with over 200 citations. A tetrazole-containing Rapamycin analog as immunomodulator and useful in the treatment of restenosis and immune and autoimmune diseases.