63775-96-2

Basic information

• Product Name: CYCLOSPORIN D
• Synonyms: CYCLOSPORIN D;Val2-cyclosporine;(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];7-L-Valinecyclosporin A;Cyclosporine IMpurity-D;7-L-valinecyclosporine A
• CAS NO: 63775-96-2
• Molecular Formula: C63H111N11O12
• Molecular Weight: 1214.62
• EINECS: 200-835-2
• Product Categories: ACTIVE PHARMACEUTICAL INGREDIENTS;Intermediates & Fine Chemicals;Peptides;Pharmaceuticals;Anti-cancer&immunity
• Mol File: 63775-96-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 148-1510C
• Boiling Point: 1294.741 °C at 760 mmHg
• Flash Point: 9 °C
• Appearance: Colorless Crystalline Solid
• Density: 1.015 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Sparingly), Ethyl Aceatate (Slightly), Methanol (Slightly)
• PKA: 13.22±0.70(Predicted)
• CAS DataBase Reference: CYCLOSPORIN D(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOSPORIN D(63775-96-2)
• EPA Substance Registry System: CYCLOSPORIN D(63775-96-2)

Safety Data

• Hazard Codes: F,Xn,T
• 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
• Hazardous Substances Data: 63775-96-2(Hazardous Substances Data)

Usage

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].

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.

InChI:InChI=1/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