Cyclosporin C


CAS No. : 59787-61-0

Cyclosporin C,59787-61-0
Product Details
Cat No:R009083
Synonyms:Thr2-cyclosporine;
Molecular Formula:C62H111N11O13
Molecular Weight:1218.6 g/mol
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Appearance:White Powder
Purity:95%(HPLC)
Cat No:R009083
Cas No:59787-61-0
Product-Name:Cyclosporin C
IUPAC Name:(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-[(1R)-1-hydroxyethyl]-33-[(E,1R,2R)-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
InChI:InChI=1S/C62H111N11O13/c1-25-26-27-39(14)52(76)51-56(80)66-49(42(17)74)60(84)67(18)32-47(75)68(19)43(28-33(2)3)55(79)65-48(37(10)11)61(85)69(20)44(29-34(4)5)54(78)63-40(15)53(77)64-41(16)57(81)70(21)45(30-35(6)7)58(82)71(22)46(31-36(8)9)59(83)72(23)50(38(12)13)62(86)73(51)24/h25-26,33-46,48-52,74,76H,27-32H2,1-24H3,(H,63,78)(H,64,77)(H,65,79)(H,66,80)/b26-25+/t39-,40+,41-,42-,43+,44+,45+,46+,48+,49+,50+,51+,52-/m1/s1
InChIKey:JTOKYIBTLUQVQV-QRVTZXGZSA-N
SMILES:CC=CCC(C)C(C1C(=O)NC(C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C)C(C)O)O
Cyclosporin C is a hydroxylated metabolite of cyclosporin A (CsA). Cyclosporin C has been found to have similar immunosuppressant activity, but lower nephrotoxicity than cyclosporin A (CsA). Cyclosporin C has also been found to have antimycotic properties.

Cyclosporin C (and other cyclosporin A (CsA) metabolites) have lower immunosuppressant activity but most likely operate under the same mechanism as cyclosporin A (CsA) described below.

Cyclosporin A (CsA) immunosuppressant activity stems from its ability to prevent T-cell activation by blocking specific cytokine transcription genes. After entering a T-cell, cyclosporin A (CsA) associates with ubiquitous cytosolic proteins called cyclophilins which aid in protein folding. Cyclosporin A (CsA) : cyclophilin complexes together bind calcineurin, (another cytosolic protein) effectively blocking the pathway to IL-2 gene transcription and T-cell activation.

Stiller, C. R., MD, and R. A. Ulan, MD. /Cyclosporin A: A Powerful Immunosuppressant./Canadian Medical Association 126 (1981): 1041-046. www.ncbi.gov. Web. 27 Aug. 2012.

Crabtree, G. R., J. Nourse, and L. Timmermann. /The Mechanism of Action of Cyclosporin A and FK506./ Clinical Immunology and Immunotherapy (1996): 40-45.www.ncbi.gov. Web. 27 Aug. 2012.

Wang, Paul C. et. al. /Isolation of 10 Cyclosporine Metabolites from Human Bile./ Drug Metabolism and Disposition 17.3 (1989): 292-96. Nih.gov. Web. 28 Oct. 2013.

Copeland, Kenneth R. /Immunosuppressive Activity of Cyclosporine Metabolites Compared and Characterized by Mass Spectrometry and Nuclear Magnetic Resonance./Clinical Chemistry 36.2 (1990): 225-29. Web. 28 Oct. 2013.

Matsuda, Staoshi. /Mechanisms of Action of Cyclosporine./ Immunopharmacology 47 (2000): 119-25. Elsevier. Web. 28 Oct. 2013.

 

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