Val2-Cyclosporine

Names

[ Name ]:
Val2-Cyclosporine

[Synonym ]:
33-[(4E)-1-Hydroxy-2-methylhex-4-en-1-yl]-6,9,18,24-tetraisobutyl-3,21,30-triisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-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-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
CyclosporinD
cyclosporine D
Val2-Cyclosporine
1,4,7,10,13,16,19,22,25,28,31-Undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone, 33-[(4E)-1-hydroxy-2-methyl-4-hexen-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-3,21,30-tris(1-methylethyl)-6,9,18,24-tetrakis(2-methylpropyl)-
33-[(4E)-1-Hydroxy-2-methyl-4-hexen-1-yl]-6,9,18,24-tetraisobutyl-3,21,30-triisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
7-L-Valinecyclosporin A
Cyclosporin Impurity 4

Biological Activity

[Description]:

Cyclosporin D, a metabolite of Cyclosporin A, is a weak immunosuppressant. Cyclosporin D is used as internal standard for quantification of Cyclosporin A[1][2]. 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)[3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vitro]

Cyclosporine D inhibits Ca2+/calmodulin dependent EF-2 phosphorylation in vitro[1].

[In Vivo]

Cyclosporine D is a potent inhibitor in vivo of phorbol ester TPA-induced biological effects in mouse skin[1].

[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.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
1294.7±65.0 °C at 760 mmHg

[ Melting Point ]:
148-151ºC

[ Molecular Formula ]:
C₆₃H₁₁₃N₁₁O₁₂

[ Molecular Weight ]:
1216.638

[ Flash Point ]:
736.8±34.3 °C

[ Exact Mass ]:
1215.857056

[ PSA ]:
275.64000

[ LogP ]:
3.70

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.468

[ Storage condition ]:
20°C

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302 + H312 + H332-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338

[ Hazard Codes ]:
F,Xn,T

[ Risk Phrases ]:
11-20/21/22-36-39/23/24/25-23/24/25

[ Safety Phrases ]:
16-36/37-45-7

[ RIDADR ]:
UN 1648 3 / PGII

[ HS Code ]:
29419090

Articles

Antimalarial activity of cyclosporins A, C and D.

Afr. J. Med. Med. Sci. 23(1) , 47-51, (1994)

Cyclosporin A (CsA) is an immunosuppressive drug widely used in organ transplants. It is also accumulated by the erythrocyte, a site that accommodates one of the stages of malaria parasite. We observe...

Enzymatic synthesis of cyclosporin A.

J. Biol. Chem. 262(36) , 17258-9, (1987)

An enzyme fraction, isolated from crude extracts of the fungus Tolypocladium inflatum, strain 7939/F, is able to synthesize the undecapeptide cyclosporin A. The formation of cyclosporin A was monitore...

In vitro and in vivo comparative studies on immunosuppressive properties of cyclosporines A, C, D and metabolites M1, M17 and M21.

Immunopharmacol. Immunotoxicol. 15(2-3) , 163-77, (1993)

Cyclosporine A (CsA) and its major metabolites: M1, M17 and M21 and two analogues: cyclosporines C (CsC) and D (CsD), were studied for their capacity to interfere with different in vitro activation pa...