Cyclosporine (USP)

HCID 5280754

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

Cyclosporine (USP)RefChem:1082793Iso Cyclosporin H Trifluoroacetic Acid SaltSR-01000075490s2286Sandimmune (TN)Restasis (TN)(2S,3R,4R,6E)-3-Hydroxy-4-methyl-2-(methylamino)-6-octenoyl-(2S)-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-D-valine 11?1)-Lactone Trifluoroacetic Acid Salt; 10-(N-Methyl-D-valine)isocyclosporin A Trifluoroacetic Acid Salt;Gengraf (TN)Neoral (TN)Ciclosporin (JP19)Spectrum5_001628
Weitere Namen anzeigen
CICLOSPORINCYCLOSPORINE ARestasissandimmuneCICLOSPORIN ANeoralCyclosporiCiclosporinOralSolution30-Ethyl-33-(1-hydroxy-2-methyl-hex-4-enyl)-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-dipropan-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-undeconeCL285
SCHEMBL3490Lopac0_000242BSPBio_001596BSPBio_003186SPECTRUM1502202BDBM86672CHEBI:91802HMS502L13

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

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

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)

Chemie und Industrie

Anwendungen · 2 Einträge

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.

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
台州开创生物医药有限公司+86-0576-88827176 +86-18906581668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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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