Cyclosporin A

Cyclosporin A is a cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It can bind to the cyclophilin and then inhibits calcineurin. Thus, it is widely used in organ transplantation to prevent rejection.

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CAT#	10-101-77
CAS	59865-13-3
Synonyms/Alias	Cyclosporine; Ciclosporin; Cyclosporin; Cyclosporin A; Cyclosporine A; Neoral; OL 27-400; Restasis; Sandimmun; Sandimmune
Chemical Name	(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-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
M.F/Formula	C62H111N11O12
M.W/Mr.	1202.61
Sequence	(R-(R,R-(E)))-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl)
Labeling Target	Peptidyl-prolyl cis-trans isomerase A; Calcium signal-modulating cyclophilin ligand; Calcineurin subunit B type 2; Peptidyl-prolyl cis-trans isomerase F, mitochondrial
Application	For prevention or treatment of organ (kidney, liver, and heart) transplant and tissue transplant rejection, rheumatoid arthritis, severe psoriasis.
Appearance	white solid powder
Purity	>98% (or refer to the Certificate of Analysis)
Biological Activity	Cyclosporin A (Cyclosporine A, Cyclosporine, Ciclosporin, CsA) is an immunosuppressive agent, binds to the cyclophilin and then inhibits calcineurin with IC50 of 7 nM in a cell-free assay, widely used in organ transplantation to prevent rejection.
Areas of Interest	Inflammation/Immunology
Functions	Calcium ion binding; Virion binding; Peptidyl-prolyl cis-trans isomerase activity
Disease	Prevention of Cardiac Transplant Rejection; Prevention of Liver Transplant Rejection; Prevention of Kidney Transplant Rejection
Target	Calcineurin

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Source#	Synthetic
Solubility	Soluble in DMSO, not in water
Shipping Condition	Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage Conditions	Dry, dark and at 0 - 4 °C
Long-term Storage Conditions	-20 °C
Organism	Human
InChI	InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1
InChI Key	PMATZTZNYRCHOR-CGLBZJNRSA-N
Canonical SMILES	CCC1C(=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)N(C(C(=O)N1)C(C(C)CC=CC)O)C)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
Isomeric SMILES	CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)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
BoilingPoint	1293.8±65.0 °C at 760 mmHg
ShelfLife	>2 years if stored properly
Melting Point	148-151°C