Cyclosporine (USP)
CICLOSPORIN · CYCLOSPORINE A · Restasis · sandimmune · CICLOSPORIN A · Neoral · Cyclospori · CiclosporinOralSolution
Identifikatoren & physikalische Daten
| CAS No. | 59865-13-3 |
|---|---|
| Summenformel | C62H111N11O12 |
| Durchschnittliche Molmasse | 1.202,6 g/mol |
| Monoisotopische Masse | 1.201,84136802 g/mol |
| SMILES | C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C |
| InChIKey | PMATZTZNYRCHOR-IMVLJIQESA-N |
| PubChem CID | 5280754 |
Chemische & physikalische Eigenschaften
| XLogP | 7,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 279 |
| H-Brücken-Donoren | 5 |
| H-Brücken-Akzeptoren | 12 |
| Frei drehbare Bindungen | 15 |
| Schwere Atome | 85 |
| Formalladung | 0 |
| Komplexität | 2.330 |
| Schmelzpunkt | 148-151°C |
| Siedepunkt | 838.63°C (rough estimate) |
| Dichte | 0.9913 (rough estimate) |
| Brechungsindex | 1.6500 (estimate) |
| Flammpunkt | 87℃ |
| Lagerbedingungen | -20°C |
| Löslichkeit | ethanol: 30 mg/mLSoluble in dimethyl sulfoxide and ethanol. Insoluble in water. |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | 13.32±0.70(Predicted) |
| Farbe | white |
| Merck | 14,2752 |
| BRN | 3647785 |
| Stabilität | Stable for 3 years as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
| InChIKey | PMATZTZNYRCHOR-CGLBZJNRSA-N |
| CAS Datenbank | 59865-13-3(CAS DataBase Reference) |
| EPA chemische Informationen | Cyclosporin A (59865-13-3) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| UN-Transportnummer | UN 1648 3 / PGII |
| Zollcode | 29419090 |
| RTECS-Nr. | GZ4120000 |
| R-Sätze (R) | 45-60-22-40-36-20/21/22-11 |
| Toxizität | LD50 in mice, rats, rabbits (mg/kg): 107, 25, >10 i.v.2329, 1480, >1000 orally (Ryffel) |
| Gefahrensymbole | T,Xn,F |
| Sicherheitshinweise (S) | 53-45-36/37-24/25-22-26-16 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 59865-13-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Cyclosporine A is a powerful immunosuppressive drug intended for preventing rejection of kidney, heart, and lung transplants. A new era in the development of immunopharmacology began with the discovery of cyclosporines. Cyclosporines are produced by mycelial mushrooms Tolypocladium inflatum, Tricoderma polysporum, and Cylindrocarpon lucidum, which are found in the ground.Cyclosporine A is the first drug to affect a specific line of protecting cells of the body. Unlike usual cytotoxics, it suppresses T-cells and acts on all cell lines simultaneously. Cyclosporine A significantly eases the ‘reception’ of transplants, and increases the possibility of treating autoimmune system diseases.
Verwenden
Cyclosporin A is a hydrophobic cyclic peptide isolated from several fungal species including Cylindrocarpon, Fusarium, Trichoderma and Tolypocladium. Cyclosporin A inhibits T-cell activation and has been marketed since 1983 as an immunosuppressant in post-allogeneic organ transplant. Cyclosporin A acts by binding to the protein, cyclophilin (immunophilin), in T-lymphocytes causing inhibition of calcineurin (protein phosphatase 2B). Cyclosporin A reduces transcription of interleukin 2, and inhibits lymphokine production, interleukin release and NO synthesis induced by interleukin 1α, lipopolysaccharides and TNFα.