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80688

Cyclosporin A

pharmaceutical secondary standard; traceable to USP and PhEur

Synonym(s):

Antibiotic S 7481F1, Cyclosporine

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About This Item

Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
59865-13-3
Molecular Weight:
1202.61
UNSPSC Code:
41116000
Beilstein/REAXYS Number:
3647785
MDL number:
MFCD00274558
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agency

traceable to Ph. Eur. C2163000, traceable to USP 1158504

storage temp.

−20°C

SMILES string

CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)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+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1

InChI key

PMATZTZNYRCHOR-CGLBZJNRSA-N

Biochem/physiol Actions

A fungal metabolite possessing potent immunosuppressive properties. It inhibits the T-cell receptor signal transduction pathway via the formation of cyclosporin A−cyclophilin complex that inhibits calcineurin (protein phosphatase 2B). Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα. Can block cytochrome c release from mitochondria.
Potent immunosuppressant; inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα; blocks cytochrome c release from mitochondria.

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Regulatory Information

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Zhong-Shun Yang et al.
Journal of medicinal chemistry, 48(14), 4608-4617 (2005-07-08)
A series of novel dihydroartemisinin derivatives were synthesized and evaluated on their immunosuppressive activity in the search for potential immunosuppressive agents with high efficacy and low toxicity. These compounds were assayed in their cytotoxicity of lymphocyte, inhibition activity on concanavalin
Jean-François Guichou et al.
Journal of medicinal chemistry, 49(3), 900-910 (2006-02-03)
Cyclophilin A is involved in many cellular processes, including protein folding and intracellular transports. Because cyclophilin A has been shown to interact with HIV-1 gag proteins and to enhance the viral infectivity, nonimmunosuppressive cyclophilin A ligands may represent a new
Mau-Sun Chang et al.
Journal of natural products, 68(1), 11-13 (2005-02-01)
From the methanolic extract of the leaves of Ficus ruficaulis Merr. var. antaoensis, 5-O-beta-D-glucopyranosyl-6-hydroxyangelicin (1), 6-O-beta-D-glucopyranosyl-5-hydroxyangelicin (2), 5,6-O-beta-D-diglucopyranosylangelicin (3), 8-O-beta-D-glucopyranosyl-5-hydroxypsoralen (4), 5-O-beta-D-glucopyranosyl-8-hydroxypsoralen (5), 3,4,5-trihydroxydehydro-alpha-ionol-9-O-beta-D-glucopyranoside (6), rutin (7), and isoquercitrin (8) were isolated. The structures of compounds 1-4 were elucidated by
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