WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H522628
CAS#: 473545-11-8
Description: UNIL088 is a water-soluble prodrug of cyclosporine A (CsA) designed for topical ocular delivery. The pro-moiety is grafted via an ester function to CsA and the solubilizing group is a phosphate ion. UNIL-088 can be rapidly hydrolysed under physiological conditions, and can retain a long shelf-life in aqueous media. UNIL-088 is more stable at pH 5 than at pH 7 with conversion rate constant of 3.2 x 10(-3) and 26.0 x 10(-3)days(-1), respectively.
Hodoodo Cat#: H522628
Name: UNIL-088
CAS#: 473545-11-8
Chemical Formula: C73H128N13O22P
Exact Mass: 1,569.90
Molecular Weight: 1,570.870
Elemental Analysis: C, 55.82; H, 8.21; N, 11.59; O, 22.41; P, 1.97
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Synonym: UNIL-088, UNIL 088, UNIL088, Cyclosporin A
IUPAC/Chemical Name: (1R,2R,E)-1-((2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-ethyl-11,17,26,29-tetraisobutyl-14,32-diisopropyl-1,7,10,16,20,23,25,28,31-nonamethyl-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl)-2-methylhex-4-en-1-yl N-(N-((1-acetoxyethoxy)carbonyl)-O-phosphono-L-seryl)-N-methylglycinate
InChi Key: INYOUNWJPIAZGW-VITLZLMDSA-N
InChi Code: InChI=1S/C73H128N13O22P/c1-28-30-31-45(15)61(108-57(89)37-80(21)68(96)51(38-105-109(102,103)104)77-73(101)107-49(19)106-48(18)87)60-65(93)76-50(29-2)67(95)79(20)36-56(88)81(22)52(32-39(3)4)64(92)78-58(43(11)12)71(99)82(23)53(33-40(5)6)63(91)74-46(16)62(90)75-47(17)66(94)83(24)54(34-41(7)8)69(97)84(25)55(35-42(9)10)70(98)85(26)59(44(13)14)72(100)86(60)27/h28,30,39-47,49-55,58-61H,29,31-38H2,1-27H3,(H,74,91)(H,75,90)(H,76,93)(H,77,101)(H,78,92)(H2,102,103,104)/b30-28+/t45-,46+,47-,49?,50+,51+,52+,53+,54+,55+,58+,59+,60+,61-/m1/s1
SMILES Code: O=C(O[C@H]([C@@H](C/C=C/C)C)[C@@H](C(N1)=O)N(C)C([C@H](C(C)C)N(C)C([C@H](CC(C)C)N(C)C([C@H](CC(C)C)N(C)C([C@@H](C)NC([C@H](C)NC([C@H](CC(C)C)N(C)C([C@H](C(C)C)NC([C@H](CC(C)C)N(C)C(CN(C)C([C@@H]1CC)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CN(C([C@H](COP(O)(O)=O)NC(OC(OC(C)=O)C)=O)=O)C
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: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 1,570.87 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1. Lallemand, F.; Varesio, E.; Felt-Baeyens, O.; Bossy, Leila; Hopfgartner, G.; Gurny, R. Biological conversion of a water-soluble prodrug of cyclosporine A. European Journal of Pharmaceutics and Biopharmaceutics (2007), 67(2), 555-561.
2. Lallemand, F.; Behar-Cohen, F.; Felt-Baeyens, O.; Rudaz, S.; Furrer, P.; Besseghir, K.; Dumont, J.-M.; Gurny, R. Cyclosporine A prodrug for topical delivery to the eye. Ocular Pharmacology and Therapeutics--ISOPT, Proceedings of the International Symposium, 5th, Monte Carlo, Monaco, Mar. 11-14, 2004 (2004), 105-109.
3. Lallemand, Frederic; Perottet, Philippe; Felt-Baeyens, Olivia; Kloeti, Werner; Philippoz, Florence; Marfurt, Judith; Besseghir, Kamel; Gurny, RobertA water-soluble prodrug of cyclosporine A for ocular application: A stability study. European Journal of Pharmaceutical Sciences (2005), 26(1), 124-129.
4. Lallemand, F.; Furrer, P.; Felt-Baeyens, O.; Gex-Fabry, M.; Dumont, J.-M.; Besseghir, K.; Gurny, R. A novel water-soluble cyclosporine A prodrug: ocular tolerance and in vivo kinetics. International Journal of Pharmaceutics (2005), 295(1-2), 7-14.
5. Hamel, A. R.; Hubler, F.; Mutter, M. Water-soluble prodrugs of cyclosporine A with tailored conversion rates. Journal of Peptide Research (2005), 65(3), 364-374.
6. Lallemand, F.; Felt-Baeyens, O.; Rudaz, S.; Hamel, A. R.; Hubler, F.; Wenger, R.; Mutter, M.; Besseghir, K.; Gurny, R.Conversion of cyclosporine A prodrugs in human tears vs rabbits tears. European Journal of Pharmaceutics and Biopharmaceutics (2005), 59(1), 51-56.
7. Wenger, Roland; Mutter, Manfred; Hamel, Arnaud; Hubler, Francis Preparation of cyclic undecapeptides for use as prodrugs. PCT Int. Appl. (2002), WO 2002085928 A2 20021031.
