WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 414667
CAS#: 135548-15-1
Description: Oxeclosporin is a hydroxyethyl derivative of serine(8)-cyclosporine; inhibits proliferation and functions of lymphocytes.
MedKoo Cat#: 414667
Name: Oxeclosporin
CAS#: 135548-15-1
Chemical Formula: C64H115N11O14
Exact Mass: 1261.8625
Molecular Weight: 1262.69
Elemental Analysis: C, 60.88; H, 9.18; N, 12.20; O, 17.74
This product is not in stock, which may be available by custom synthesis.
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Synonym: Oxeclosporin; Sdz imm 125
IUPAC/Chemical Name: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-((1R,2R,E)-1-hydroxy-2-methylhex-4-en-1-yl)-12-((2-hydroxyethoxy)methyl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,15,19,25,28-octamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
InChi Key: XZDDMPMZGYEESG-VNHFGJPGSA-N
InChi Code: InChI=1S/C64H115N11O14/c1-24-26-27-42(15)54(78)53-58(82)66-44(25-2)59(83)69(17)34-50(77)70(18)46(30-36(3)4)57(81)68-51(40(11)12)63(87)71(19)47(31-37(5)6)56(80)65-43(16)55(79)67-45(35-89-29-28-76)60(84)72(20)48(32-38(7)8)61(85)73(21)49(33-39(9)10)62(86)74(22)52(41(13)14)64(88)75(53)23/h24,26,36-49,51-54,76,78H,25,27-35H2,1-23H3,(H,65,80)(H,66,82)(H,67,79)(H,68,81)/b26-24+/t42-,43+,44+,45-,46+,47+,48+,49+,51+,52+,53+,54-/m1/s1
SMILES Code: CC[C@@H]1NC([C@@H](N(C([C@@H](N(C([C@@H](N(C([C@@H](N(C([C@H](NC([C@@H](NC([C@@H](N(C([C@H](C(C)C)NC([C@@H](N(C(CN(C1=O)C)=O)C)CC(C)C)=O)=O)C)CC(C)C)=O)C)=O)COCCO)=O)C)CC(C)C)=O)C)CC(C)C)=O)C)C(C)C)=O)C)[C@@H]([C@@H](C/C=C/C)C)O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 1262.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Billich A, Vyplel H, Grassberger M, Schmook FP, Steck A, Stuetz A. Novel cyclosporin derivatives featuring enhanced skin penetration despite increased molecular weight. Bioorg Med Chem. 2005 May 2;13(9):3157-67. doi: 10.1016/j.bmc.2005.02.049. PMID: 15809151.
2: Hiestand PC, Gräber M, Hurtenbach U, Herrmann P, Cammisuli S, Richardson BP, Eberle MK, Donatsch P, Ryffel B, Borel JF. New cyclosporine derivative SDZ IMM 125: in vitro and in vivo pharmacologic effects and toxicologic evaluation. Transplant Proc. 1993 Feb;25(1 Pt 1):691-2. PMID: 8438439.
3: Vickers AE, Meyer E, Dannecker R, Keller B, Tynes RE, Maurer G. Human liver cytochrome P4503A biotransformation of the cyclosporin derivative SDZ IMM 125. Drug Metab Dispos. 1995 Mar;23(3):321-6. PMID: 7628296.
4: Vickers AE, Jimenez RM, Spaans MC, Pflimlin V, Fisher RL, Brendel K. Human and rat lung biotransformation of cyclosporin A and its derivatives using slices and bronchial epithelial cells. Drug Metab Dispos. 1997 Jul;25(7):873-80. PMID: 9224782.
5: Kawai R, Lemaire M, Steimer JL, Bruelisauer A, Niederberger W, Rowland M. Physiologically based pharmacokinetic study on a cyclosporin derivative, SDZ IMM 125. J Pharmacokinet Biopharm. 1994 Oct;22(5):327-65. doi: 10.1007/BF02353860. PMID: 7791036.
6: Witkamp L, Zonneveld IM, Jung EG, Schopf RE, Christophers E, Grossman R, Meffert H, Belaich S, Mahrle G, Van Joost T, et al. Efficacy and tolerability of multiple-dose SDZ IMM 125 in patients with severe psoriasis. Br J Dermatol. 1995 Jul;133(1):95-103. doi: 10.1111/j.1365-2133.1995.tb02500.x. PMID: 7669649.
7: Vickers AE, Alegret M, Meyer E, Smiley S, Guertler J. Hydroxyethyl cyclosporin A induces and decreases P4503A and P-glycoprotein levels in rat liver. Xenobiotica. 1996 Jan;26(1):27-39. doi: 10.3109/00498259609046686. PMID: 8851819.
8: Bruelisauer A, Kawai R, Misslin P, Lemaire M. Absorption and disposition of SDZ IMM 125, a new cyclosporine derivative, in rats after single and repeated administration. Drug Metab Dispos. 1994 Mar-Apr;22(2):194-9. PMID: 8013274.
9: Vickers AE, Fisher RL, Brendel K, Guertler J, Dannecker R, Keller B, Fischer V. Sites of biotransformation for the cyclosporin derivative SDZ IMM 125 using human liver and kidney slices and intestine. Comparison with rat liver slices and cyclosporin A metabolism. Drug Metab Dispos. 1995 Mar;23(3):327-33. PMID: 7628297.
10: Grub S, Trommer WE, Wolf A. Role of antioxidants in the O-hydroxyethyl-D-(Ser)8-cyclosporine A (SDZ IMM125)-induced apoptosis in rat hepatocytes. Biochem Pharmacol. 2002 Dec 15;64(12):1725-36. doi: 10.1016/s0006-2952(02)01384-9. PMID: 12445861.
