Cyclosporine (USP)
Grundinformationen
- CAS
59865-13-3- Standard-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- Summenformel
- C62H111N11O12
- Durchschnittliche Molmasse
- 1.202,6 g/mol
- Monoisotopische Masse
- 1.201,84136802
Namen und Bezeichner
- Bevorzugter Name
- Cyclosporine (USP)
- IUPAC
- 30-ethyl-33-[(E)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
- Englischer Name
- Cyclosporin A
- Summenformel
- C62H111N11O12
- Molmasse
- 1202.61
Namen und Synonyme
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Datenbank-Bezeichner
- CAS
59865-13-3- PubChem CID
- 5280754
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 7,5
- Polarare Oberfläche (TPSA)
- 279 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 12
- Frei drehbare Bindungen
- 15
- Schwere Atome
- 85
- Formalladung
- 0
- Komplexität
- 2.330
Physikochemische Eigenschaften
- Schmelzpunkt
- 148 · 148-151°C
- Siedepunkt
- 838.63 °C · 838.63°C (rough estimate)
- Dichte
- 0.9913 · 0.9913 (rough estimate)
- Brechungsindex
- 1.65 · 1.6500 (estimate)
- Flammpunkt
- 87 ℃ · 87℃
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 30 mg/mL · ethanol: 30 mg/mL
- Aggregatzustand
- solid
- pka
- 13.32 · 13.32±0.70(Predicted)
- Farbe
- white
- Wasserlöslichkeit
- Soluble in dimethyl sulfoxide and ethanol. Insoluble in water.
- Merck
- 14 · 14,2752
- BRN
- 3647785 · 3647785
- Stabilität
- 3 years · 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 · 59865-13-3(CAS DataBase Reference)
- EPA chemische Informationen
- Cyclosporin A (59865-13-3)
Sicherheit und Regulatorisches
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29419090
- RTECS-Nr.
- GZ4120000
- risk_code
- 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)
- hazard_code
- T,Xn,F
- safety_code
- 53-45-36/37-24/25-22-26-16
- Speicherklasse
- 10 - Combustible liquids
- Giftige Stoffe Daten
- 59865-13-3(Hazardous Substances Data)
Chemie und Industrie
Anwendungen
BeschreibungCyclosporine 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.
VerwendenCyclosporin 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.
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Ergänzende Hinweise
DefinitionChEBI: A cyclic nonribosomal peptide of eleven amino acids; an immunosuppressant drug widely used in post-allogeneic organ transplant to reduce the activity of the patient's immune system, and therefore the risk of organ rejection. Also causes reversible inhibiti n of immunocompetent lymphocytes in the G0- and G1-phase of the cell cycle.
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