Cyclosporin D is a nonpolar cyclic oligopeptide and a novel metabolite of Cyclosporin A, which is an immunosuppressant agent that binds cyclophilin D, inhibiting the phosphatase activity of calcineurin in T cells. Cyclosporin D is a minor analogue of the cyclosporin complex produced by Trichoderma.
Physicochemical Properties
| Molecular Formula | C₆₃H₁₁₃N₁₁O₁₂ |
| Molecular Weight | 1216.64 |
| Exact Mass | 1215.857 |
| CAS # | 63775-96-2 |
| PubChem CID | 5287819 |
| Appearance | White to off-white solid powder |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 1294.7±65.0 °C at 760 mmHg |
| Melting Point | 148-151ºC |
| Flash Point | 736.8±34.3 °C |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.468 |
| LogP | 3.7 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 15 |
| Heavy Atom Count | 86 |
| Complexity | 2360 |
| Defined Atom Stereocenter Count | 12 |
| SMILES | C/C=C/C[C@@H](C)[C@H]([C@H]1C(=O)N[C@H](C(=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)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)C)O |
| InChi Key | ZNVBEWJRWHNZMK-SYOLRUPNSA-N |
| InChi Code | 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 |
| 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 |
| Synonyms | Cyclosporin DVal2-cyclosporine |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In vitro, EF-2 phosphorylation that is dependent on Ca2+/calmodulin is inhibited by cyclosporin D [1]. |
| ln Vivo | In vivo biological effects of phorbol ester TPA on mouse skin are strongly inhibited by cyclosporine D [1]. |
| References |
[1]. 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]. 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]. 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. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~25 mg/mL (~20.55 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.8219 mL | 4.1097 mL | 8.2194 mL | |
| 5 mM | 0.1644 mL | 0.8219 mL | 1.6439 mL | |
| 10 mM | 0.0822 mL | 0.4110 mL | 0.8219 mL |