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CYCLOSPORIN D

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CYCLOSPORIN D Basic information

Product Name:
CYCLOSPORIN D
Synonyms:
  • CYCLOSPORIN D
  • (3R,4R)-3-Hydroxy-N-methyl-5-[(E)-1-propenyl]-cyclo(L-Leu-L-Val-Sar-N-methyl-L-Leu-L-Val-N-methyl-L-Leu-L-Ala-D-Ala-N-methyl-L-Leu-N-methyl-L-Leu-N-methyl-L-Val-)
  • (3R,4R)-3-Hydroxy-N-methyl-5-[(E)-1-propenyl]cyclo(L-Leu-L-Val-Sar-N-methyl-L-Leu-L-Val-N-methyl-L-Leu-L-Ala-D-Ala-N-methyl-L-Leu-N-methyl-L-Leu-N-methyl-L-Val-)
  • Cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-valyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl]
  • Val2-cyclosporine
  • 7-L-Valinecyclosporin A
  • Cyclosporin D, froM MicroMonospora
  • Cyclosporine IMpurity-D
CAS:
63775-96-2
MF:
C63H113N11O12
MW:
1216.64
EINECS:
806-434-4
Product Categories:
  • Anti-cancer&immunity
  • ACTIVE PHARMACEUTICAL INGREDIENTS
  • Intermediates & Fine Chemicals
  • Peptides
  • Pharmaceuticals
Mol File:
63775-96-2.mol
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CYCLOSPORIN D Chemical Properties

Melting point:
148-1510C
alpha 
D20 -245° (c = 0.52 in CHCl3); D20 -211° (c = 0.51 in methanol)
Boiling point:
1294.7±65.0 °C(Predicted)
Density 
1.015±0.06 g/cm3(Predicted)
Flash point:
9 °C
storage temp. 
-20°C Freezer
solubility 
Chloroform (Sparingly), Ethyl Aceatate (Slightly), Methanol (Slightly)
form 
Colorless to off-white crystalline solid.
pka
13.22±0.70(Predicted)
color 
White to Off-White
InChIKey
YJDYDFNKCBANTM-QCWCSKBGSA-N
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Safety Information

Hazard Codes 
F,Xn,T
Risk Statements 
11-20/21/22-36-39/23/24/25-23/24/25
Safety Statements 
16-36/37-45-7
RIDADR 
UN 1648 3 / PGII
WGK Germany 
2
HS Code 
29419090
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CYCLOSPORIN D Usage And Synthesis

Chemical Properties

Colorless Crystalline Solid

Uses

A group of nonpolar cyclic oligopeptides with immunosupppressant activity.

Uses

Cyclosporin D is a minor analogue of the cyclosporin family which is only weakly immunologically active. Cyclosporin D is a potent inhibitor of tumour-promoting phorbol esters on mouse skin in vivo, and a potent inhibitor of calcium/calmodulin-dependent EF-2 phosphorylation in vitro.

Biological Activity

cyclosporin d is an immunosuppressive agent [1].cyclosporin d (csd) is an analogue of cyclosporine a with weak immunosuppressive activity. cyclosporin d has been used as an internal standard for the quantification of cyclosporin a. in human multidrug-resistant ovarian cancer cells, cyclosporin d significantly overcame adriamycin resistance [2]. in lymphocyte, csd weakly inhibited pha-, pwm-, and pma + ca2+-induced cell proliferation [3].in mice, csd inhibited edema in mouse ear and alkaline phosphatase activity in mouse skin induced by tpa by 98% and 88%, respectively. in cytosol of mouse pancreas, csd inhibited the ca2+/calmodulin-dependent phosphorylation of the elongation factor 2 (ef-2) and the tpa-induced increase of ef-2 [1]. cyclosporin d was effective in inhibiting p. falciparum parasite in vitro and p. berghei malaria parasite development in vivo when administered orally [4].

storage

+4°C

References

[1]. gschwendt m, kittstein w, marks f. 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, 150(2): 545-551.
[2]. mizuno k, furuhashi y, misawa t, et al. modulation of multidrug resistance by immunosuppressive agents: cyclosporin analogues, fk506 and mizoribine. anticancer res, 1992, 12(1): 21-25.
[3]. sadeg n, pham-huy c, rucay p, et al. in vitro and in vivo comparative studies on immunosuppressive properties of cyclosporines a, c, d and metabolites m1, m17 and m21. immunopharmacol immunotoxicol, 1993, 15(2-3): 163-177.
[4]. uadia po1, ezeamuzie ic, ladan mj, et al. antimalarial activity of cyclosporins a, c and d. afr j med med sci, 1994, 23(1): 47-51.

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