Cyclosporin D

Cyclosporin D, a metabolite of Cyclosporin A, is a weak immunosuppressant. Cyclosporin D is used as internal standard for quantification of Cyclosporin A. Cyclosporin A is a potent immunosuppressant drug, suppress T cell activation by inhibiting calcineurin and the calcineurin-dependent transcription factors nuclear factor of activated T cells (NFAc).

Product information

CAS Number: 63775-96-2

Molecular Weight: 1216.64

Formula: C63H113N11O12

Chemical Name: (3S, 6S, 9S, 12R, 15S, 18S, 21S, 24S, 30S, 33S)-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, 30-tri(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

Smiles: C/C=C/C[C@@H](C)[C@@H](O)[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C

InChiKey: ZNVBEWJRWHNZMK-SYOLRUPNSA-N

InChi: InChI=1S/C63H113N11O12/c1-26-27-28-41(16)53(76)52-57(80)67-49(38(10)11)61(84)68(19)33-48(75)69(20)44(29-34(2)3)56(79)66-50(39(12)13)62(85)70(21)45(30-35(4)5)55(78)64-42(17)54(77)65-43(18)58(81)71(22)46(31-36(6)7)59(82)72(23)47(32-37(8)9)60(83)73(24)51(40(14)15)63(86)74(52)25/h26-27,34-47,49-53,76H,28-33H2,1-25H3,(H,64,78)(H,65,77)(H,66,79)(H,67,80)/b27-26+/t41-,42+,43-,44+,45+,46+,47+,49+,50+,51+,52+,53-/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: To be determined

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Cyclosporine D inhibits Ca2+/calmodulin dependent EF-2 phosphorylation in vitro.

In Vivo:

Cyclosporine D is a potent inhibitor in vivo of phorbol ester TPA-induced biological effects in mouse skin.

References:

1. Gschwendt M, et al. The weak immunosuppressant cyclosporine D as well as the immunologically inactive cyclosporine H are potent inhibitors in vivo of phorbol ester TPA-induced biological effects in mouse skin and of Ca2+/calmodulin dependent EF-2 phosphorylation in vitro. Biochem Biophys Res Commun. 1988 Jan 29;150(2):545-51.
2. Kaiser P, et al. A new approach for the determination of immunosuppressive drugs using HPLC-MS/MS and Cs+ adducts. Ger Med Sci. 2006 Jan 18;4:Doc01.
3. Minguillón J, et al. Concentrations of cyclosporin A and FK506 that inhibit IL-2 induction in human T cells do not affect TGF-beta1 biosynthesis, whereas higher doses of cyclosporin A trigger apoptosis and release of preformed TGF-beta1. J Leukoc Biol. 2005 May;77(5):748-58. Epub 2005 Feb 16.

Products are for research use only. Not for human use.