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Key Documents

SML1018

Sigma-Aldrich

Cyclosporin A

≥95% (HPLC), DMSO solution, calcineurin inhibitor

Synonym(s):

CsA, Cyclosporine

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About This Item

Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
59865-13-3
Molecular Weight:
1202.61
EC Number:
200-664-3
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Cyclosporin A, Ready Made Solution, 1 mg/mL in DMSO

form

DMSO solution

Quality Level

200

storage condition

protect from light

concentration

1 mg/mL in DMSO

shipped in

dry ice

storage temp.

−20°C

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+

InChI key

PMATZTZNYRCHOR-IMVLJIQESA-N

Application

Cyclosporin A has been used to test its toxic effect on perfused 3D proximal tubule model.

Biochem/physiol Actions

Cyclosporin A is a non-polar cyclic oligopeptide produced by the fungus Tolypocladium inflatum. It is a potent immunosuppressive agent, affecting primarily T-lymphocytes. It has been shown to inhibit the functioning of several nuclear proteins involved in T-cell activation at the level of mRNA transcription. It forms a complex with its intracellular receptor cyclophilin, which can then bind to calcineurin, a Ca2+- and calmodulin-dependent protein phosphatase, inhibiting its enzymatic activity. CsA was found to suppress the replication of hepatitis C virus genome in cultured hepatocytes. At concentrations >10 nM, CsA protected isolated hepatocytes against the action of phalloidin. CsA can inhibit IL2 production resulting from T cell activation via Calcineurin inhibition.
An extensive list of references has been reported, including a comprehensive review of analytical properties.
Cyclosporin A is generally given subsequent to transplant surgery to prevent rejection. In addition to its beneficial effects in organ transplantation, cyclosporin (CyA) exhibits nephrotoxic side effects.

Other Notes

Light sensitive

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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