UNIL-088 | CAS#473545-11-8 | Prodrug of Cyclosporine

MedKoo Cat#: 522628 | Name: UNIL-088

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

UNIL-088

CAS#473545-11-8

Theoretical Analysis

MedKoo Cat#: 522628

Name: UNIL-088

CAS#: 473545-11-8

Chemical Formula: C73H128N13O22P

Exact Mass: 1569.9034

Molecular Weight: 1570.87

Elemental Analysis: C, 55.82; H, 8.21; N, 11.59; O, 22.41; P, 1.97

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

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

Instruction

View handling instruction

Preparing Stock Solutions

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

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.